138 Magical Things to Do in Boston: December 2025
When:
Monday, Dec 01, 2025 7:00a -
Wednesday, Dec 31, 2025 11:59p
Monday, Dec 01, 2025 7:00a -
Wednesday, Dec 31, 2025 11:59p
Where:
Boston
Surrounding Areas
Boston, MA
Admission:
$0+
Categories:
Art, Date Idea, Drinks, Festivals & Fairs, Food, Good for Groups, History, Meetup, Movies, Music, Nature, Nightlife, Party, Photoworthy, Seasonal, Shopping
Happy final month of 2025, my Boston friends. It’s time to close out the year with some holiday cheer. Get ready for community tree lightings, free movie screenings, cozy meet-ups, festive bar pop-ups, holiday shows, and so much more.
It’s the most magical time of the year in Boston. Happy holidays from us to you!
By Yelena Nicolle Salvador
Experiences listed chronologically by categories.
LIGHTINGS & STROLLS
1) Copley Square Tree Lighting & Reopening of Copley Square
When: Mon. 12/1
Where: Back Bay
Cost: Free
Info: Head to the newly renovated Copley Square. Since 2022, this lighting ceremony has been put on pause, so don’t miss your chance to see its grand return. There will be live music by local groups like the Boston Pops Brass Ensemble and special appearances from Santa and Rudolph. Munch on complimentary cookies and feel the holiday cheer in the heart of the city.
2) 31 Nights of Light at the Prudential Center
When: Daily until Wed. 12/31
Where: Back Bay
Cost: Free
Info: Look out the window to see the top of the Pru in bursting with color every night during the month of December. For the 18th year, this iconic Boston building will be honoring 28 different nonprofit organizations and 3 holidays.
3) Somerville Illuminations 2025
When: Daily until Fri. 1/1
Where: Somerville
Cost: Free
Info: One of the best holiday traditions in the Boston area is heading over to Somerville to catch the annual Illuminations event. Wander around the neighborhood to spot houses, triple-deckers, and local businesses that go all out with giant inflatables, thousands of lights, and synchronized musical displays. Check out the free interactive map to find your favorites! Keep in mind that folks can add their locations until 12/11, so if you want a full experience, wait until then — however, plenty of people have decorations up already! And mark your calendar for the Illuminations Bike Tour on 12/13 where you can meet new friends while exploring the lights.
When: Daily until Thu. 1/2
Where: Downtown
Cost: Free
Info: This quirky animal-nutcracker art installation is back and scattered around Downtown Crossing. Bundle up and spot 12 of the 16-foot, illuminated nutcracker bodies with silly and very realistic animal heads. You’ll find a rhino, a penguin, and more!
5) Boston Landing Holiday Tree Lighting
When: Wed. 12/3
Where: Brighton
Cost: Free
Info: Boston Landing is hosting their annual tree lighting in the middle of Athletes Park. Dance to the tunes of a live DJ and sing along with the tunes of the holiday carolers. There will be storytime, free goodies, complimentary mini photo sessions, crafts, DIY cookie kits, and other fun surprises.
6) South Boston Holiday Stroll
When: Thu. 12/4
Where: Southie
Cost: Free
Info: Say hello to Santa as he waves from an antique firetruck and makes his way around Southie. There will be complimentary hot cocoa and sweet treats at every stop, so cheer him on and enjoy live music too. Don’t miss the holiday tree lighting, strolling carolers, and more.
7) Beacon Hill Holiday Stroll & Tree Lighting
When: Thu. 12/4
Where: Beacon Hill
Cost: Free
Info: One of Boston’s most iconic neighborhoods will be transforming into a winter wonderland. Enjoy car-free streets while shopping at some of the city’s most quaint small businesses for the perfect gifts. There will be roaming carolers, live music, and refreshments. Then, watch the lighting of the Beacon Hill tree at 7PM sharp.
8) Boston Common Tree Lighting Ceremony
When: Thu. 12/4
Where: Boston Common
Cost: Free
Info: Join the festivities for the 84th Annual Boston Common Tree Lighting Ceremony. Explore the sampling village where there will be giveaways and complimentary refreshments. Get ready for live music and other performances. And join Santa, Rudolph the Red-Nosed Reindeer, and Mayor Wu as they turn on the lights for the Nova Scotia tree.
9) Commonwealth Avenue Mall Holiday Lights
When: Thu. 12/4
Where: Back Bay
Cost: Free
Info: Immediately after the Boston Common Tree Lighting Ceremony, the switch will be flipped to turn on the lights along the Comm Ave Mall. Join your neighbors as you find a spot along the boulevard and watch the street come to life.
10) Light Up Seaport
When: Fri. 12/5
Where: Seaport
Cost: Free
Info: Join your neighbors at the 9th Annual Light Up Seaport. Get there early for a chance to get a free Betty the Yeti beanie if you’re a VIP Insider (P.S. it’s free to join). Say hi to her as she stops by from the Himalayas. Jam out to DJ tunes, listen to live music, enjoy complimentary treats, and watch the giant tree light up on the Seaport Common.
11) SOLSTICE: Reflections on Winter Light
When: Daily except Mondays & Thursdays, starting Fri. 12/5 until Sun. 12/21
Where: Mt. Auburn
Cost: $38.75
Info: Mount Auburn Cemetery will be illuminated with unique light displays by artists. Grab a ticket and stroll around the property to embark on an adventure that combines music and large-scale light installations. There will even be an indoor experience with live music and candles. This is a unique way to celebrate the holiday season and reflect on the year, so come check it out to celebrate the Winter solstice.
12) Boston Mayor’s Enchanted Trolley Tour & Tree Lightings
When: Sat. 12/6 - Sun. 12/7
Where: Boston
Cost: Free
Info: The Mayor’s holiday trolley tour is back for its 29th year. Say hi to Mayor Wu and Santa as they light trees in 16 different neighborhoods around the city. There will be giveaways, photo-ops, and other fun surprises.
13) Open Newbury Street Winter 2025: Holiday Stroll
When: Sun. 12/7
Where: Back Bay
Cost: Free
Info: For one day only, Open Newbury Street will be back to ring in the holiday season. Enjoy a car-free stroll along one of Boston’s most famous streets. Enjoy the holiday lights, specials from local businesses, and other activations.
14) Christmas on the East Boston Greenway
When: Sun. 12/7
Where: East Boston
Cost: Free
Info: Cross the Harbor and stop by East Boston’s Bremen Street Park. There will be a holiday show by Riverside Theater Works, complimentary hot cocoa & sweet treats, as well as crafts, games, and a visit from Santa and Mrs. Claus. Don’t miss the luminaria candle-lit stroll too.
15) Generals Bridge & Park Tree Lighting
When: Sun. 12/7
Where: Quincy
Cost: Free
Info: Join the community for this special lighting ceremony at Quincy’s Generals Park. Active and retired military will be honored at this event where family and friends can sign the name of those who have served on a yellow ribbon that will be placed on the tree.
16) Union Square Jingle: Shop, Single, & Mingle
When: Sun. 12/7
Where: Union Square
Cost: Free
Info: Head to Union Square for a day of holiday cheer as locally-owned businesses will be dressed up in sparkling lights, decorations, and inflatables. During this stroll, you can spot fun characters and carolers. Vote for your favorite storefront. Follow the Festivus Trail with fun balloon sculptures. And enjoy special deals from local restaurants and shops.
When: Daily, starting Thu. 12/4 until Sat. 1/3
Where: Jamaica Plain
Cost: Free
Info: The First Baptist Church will be lit with a special holiday projection show every night. Catch ‘Twas the Night Before Solstice’ where you can spot the famous albino squirrel and listen to synchronized music from your phone in Spanish or English! Don’t forget to check out the first-ever South Street Illumination display and the opening party for both activations where there will also be hot cocoa and light refreshments.
18) Fenway Tree Lighting & Luminary Walk 2025
When: Wed. 12/10
Where: Fenway
Cost: Free
Info: Get ready for an evening of holiday cheer in the beloved Fenway neighborhood. Stop by the Fenway Community Center’s pre-party to craft and meet the Red Sox’s Wally and Tessie. Watch the tree light up right outside the Kelleher Rose Garden while enjoying complimentary hot cocoa, cider, and refreshments. Then, walk with neighbors to The Station and see the tree farm while sipping a fun cocktail from Cisco’s The Fenway Chalet.
When: Wed. 12/10
Where: South End
Cost: Free
Info: Enjoy a festive evening as you explore the South End neighborhood. There will be local shops with beautiful decorations that will be serving up special deals and discounts for everyone to enjoy. Find one-of-a-kind holiday gifts, participate in raffles, and more.
20) Charlestown’s Holiday Night Out
When: Wed. 12/10
Where: Charlestown
Cost: Free
Info: Make your way to Charlestown and take a holiday stroll around the neighborhood. Local restaurants and small businesses will be decorated and offering holiday gifts, seasonal bites, and themed drinks for purchase. Shop small this season and enjoy fun surprises.
21) The Anchor Winter Garden Holiday Tree Lighting
When: Thu. 12/11
Where: Charlestown
Cost: Free
Info: The Anchor’s Winter Garden is making its grand return after a break last year. Don’t miss this special event where 175 trees along the waterfront will be illuminated with the Boston skyline as its backdrop.
When: Fri. 12/12
Where: North End
Cost: Free
Info: Head to Boston’s Little Italy for the 18th Annual North End Holiday Stroll. As you grab some Italian sweets and treats, walk around the neighborhood for some fun deals at local businesses. There will also be roaming carolers, a visit from Santa, and more.
When: Sat. 12/13
Where: Seaport
Cost: Free
Info: Wander around Seaport and spot all of the fun decorations. Say hi to Betty the Yeti, grab a portrait in front of the big tree in Seaport Common, shop great deals at your favorite shops, and so much more. Get there early for a free tote while supplies last too.
24) Adams Village Holiday Stroll
When: Sat. 12/13
Where: Dorchester
Cost: Free
Info: Explore the Adams Village neighborhood in Dorchester while shopping small on this holiday stroll. Enjoy discounts at local businesses, festive treats & drinks, and visits from Santa. There will even be live music, giveaways, and crafts for all.
25) 4th Annual Hanukkah Celebration at Arsenal Yards
When: Mon. 12/15
Where: Watertown
Cost: Free
Info: Arsenal Yards will be hosting their 4th annual public menorah lighting ceremony and celebration. Get ready for live music and complimentary treats, as well as crafts, games, and a live fire dance performance. There will even be an interactive light display and a special gelt drop.
26) The Speedway Holiday Stroll
When: Sat. 12/20 - Sun. 12/21
Where: Brighton
Cost: Free
Info: Join the Brighton Bazaar and the Charles River Speedway for the annual Speedway Holiday Stroll. Throughout the weekend, there will be over 60 small businesses, special deals, and themed drinks and food. Find the perfect gift for yourself or a loved one at this sip & shop stroll.
27) Menorah Lighting
When: Sun. 12/21
Where: Seaport
Cost: Free
Info: Make your way to Seaport and celebrate Hanukkah with the annual Menorah Lighting Celebration. There will be complimentary kosher jelly donuts and chocolate gelt for all. Bring your friends and family to experience the Hanukkah season.
28) 10+ Places to See Holiday Lights Around Boston and New England
When: December
Where: Boston & New England
Cost: Varies
Info: Adventure through the city and find your favorite holiday lighting display like the North End’s holiday trellis and Martin Park’s ship! Stop by the Festival of Trees where you can see a railroad display in beautifully lit gardens, as well as the NE Botanical Garden’s Night Lights displays featuring the 10-foot-long Rainbow Tunnel!
WINTER MARKETS
When: Daily until Wed. 12/24
Where: Brighton
Cost: Free
Info: Find the perfect holiday tree for you, your friends, and your family at this tree farm. There will also be wreaths, stands, and other decoration goodies. Come support this local, veteran-owned business that’s been around since 1969.
When: Daily until Thu. 12/25
Where: Fenway
Cost: Free
Info: Feel the jolly holiday spirit by decorating your door, stoop, apartment, or home with a Christmas tree. There are plenty of options at this tree farm from big and tall to short, stout, and extra mini. No need to catch any splinters since the Christmas Tree For Me Team will take care of the cutting and strapping process.
When: Daily until Sun. 12/28
Where: South End
Cost: $10
Info: One of Boston’s most iconic events of the year is back — head to SoWa Power Station for the 10th Annual SoWa Winter Festival. Step into this indoor market where holiday lights will be dangling from above as you shop from over 125 small businesses. Enjoy live music, country nights, themed drinks, and other fun surprises.
4) Snowport: Magical Winter Wonderland in Boston Seaport
When: Daily until Wed. 12/31
Where: Seaport
Cost: Free
Info: It’s the most wonderful time of the year with the always highly anticipated return of Snowport. Enjoy free curling lanes, a tree market, photos with the famous Betty the Yeti, and the giant holiday market. There will be live music, over 125 small businesses that will be selling one-of-a-kind goodies, holiday cocktails, and yummy bites.
5) #ShopAAPI Holiday Night Market
When: Wed. 12/3
Where: Back Bay
Cost: Free
Info: Celebrate the creativity and talents of the local AAPI community at this holiday market. There will be over 30 small AAPI businesses that will be selling art, treats, and other items. Enjoy pop-up food stations from local chefs, book signings with AAPI authors, photo-ops, and giveaways.
6) Downtown Boston Holiday Market
When: Every Thursday to Saturday, starting Thu. 12/4 until Sat. 12/20
Where: Downtown
Cost: Free
Info: Make your way to Downtown Crossing and shop small this holiday season. Every week will feature a different rotation of unique vendors (be on the lookout for some friendly alpacas) and find the perfect gift for your loved ones. There will be a bonus Sunday on 12/21 too!
7) First Street Holiday Night Markets
When: Fridays, starting 12/5 - 12/19
Where: Cambridge
Cost: Free
Info: First Street Market will be hosting a weekly night market full of small businesses. Join local makers and find crafts, art, farm-fresh foods, and themed cocktails. There will even be live music while you sip and shop under the twinkling lights.
8) Kilroy Square Holiday Market
When: Fri. 12/5 - Sun. 12/7
Where: Quincy
Cost: Free
Info: Join the Kilroy Square Holiday Market for their final weekend of the season. Sip on a drink at the beer garden, enjoy live music, and grab a bite to eat from a good truck. Then, explore the goods of over 90 small businesses.
When: Fri. 12/5 - Sat. 12/6
Where: Cambridge
Cost: Free
Info: Head to the Holy Trinity Armenian Church for the annual Armenian Christmas Bazaar. Chefs from the church will be cooking up traditional dishes and pastries like kebabs, apricot squares, and sweet bread. Then, find the perfect gift from local makers.
10) Boston Public Market Holiday Sip & Shop
When: Fridays to Sundays, starting Fri. 12/5 until Sat. 12/21
Where: Downtown
Cost: Free
Info: Boston Public Market is hosting their annual holiday market. Grab a drink from the bar on-site and peruse the lovely local vendors from across New England who sell art, sweet treats, and other goodies. Every week, there will also be a pop-up of new vendors to explore.
11) Christkindlmarkt - German Holiday Market
When: Sat. 12/6
Where: Allston
Cost: Free
Info: You don’t need to travel far to feel like you're at a traditional European Market. Stop by the German International School Boston’s Christkindlmarkt where there will be crafts, live music, and local artisans. Be on the lookout for the highly requested return of traditional, handmade ornaments from Germany’s Erzgebirge region too.
12) Boston Women’s Holiday Market at the Huntington Theatre
When: Sat. 12/6
Where: South End
Cost: Free
Info: Boston Women’s Market is taking the stage at the beautiful Huntington Theatre where you can shop and support from over 25 small, women-owned businesses. Sip some wine and themed cocktails while you shop at this historic venue.
13) Small Mart Holiday Market at Crystal Ballroom
When: Sat. 12/6 & Sat. 12/20
Where: Somerville
Cost: Free
Info: Shop small this season at Small Mart’s Holiday Market. As you walk through the Crystal Ballroom full of dangling, glowing chandeliers that set the mood, you’ll find unique goods from over 40 artists and vintage vendors. A full bar will be available on-site too.
14) Castle Island Holiday Marketplace
When: Saturdays, starting 12/6 - 12/20
Where: Southie
Cost: Free
Info: Castle Island Brewing will be serving up seasonal and fan-favorite brews, as well as pizza and other treats, while you sip and shop from rotating vendors. Every week, you can expect a new lineup of art, vintage finds, and more. Come spread the holiday spirit at this pop-up.
15) Fenway Holiday Thrift Market by Select & B-Side
When: Sat. 12/6 - Sun. 12/7
Where: Fenway
Cost: Free
Info: Boston B-Side and Select Markets are teaming up to create a giant holiday market experience at MGM Music Hall. Shop from over 50 different businesses each day, find treasures in the $10 piles, grab some drinks, and so much more. There will also be a photobooth, festive workshops, and a food drive that you can donate to.
16) Krampusfest by Brighton Bazaar & Notch Brewing
When: Sat. 12/6 - Sun. 12/7
Where: Brighton
Cost: Free
Info: If you’re feeling naughty this holiday season, come celebrate Krampus at Krampusfest with Brighton Bazaar and Notch Brewing at the Charles River Speedway. Learn about this German tradition with a festive parade, a costume contest, live music, and more. Plus, shop from over 60 vendors who will be selling witchy wares all day and watch a wizard fight.
17) Green & Jolly Holiday Faire
When: Sun. 12/7
Where: Union Square
Cost: Free
Info: Green Tiger & Co. is hosting a Green & Jolly Holiday Faire at Upstairs at Bow. This market is extra special since it will be highlighting small, eco-friendly businesses that put the environment first while serving up unique items like jewelry, perfumes, and kitchen tools. Bring your own bag and participate in a raffle to support a local nonprofit.
18) Winter Market at Sam Adams Brewery
When: Sun. 12/7
Where: Jamaica Plain
Cost: Free
Info: Sam Adams Brewery will be decked out with holiday cheer during their Winter Market. As you sip on traditional and seasonal brews, you can enjoy live music while shopping for artisanal goods from local makers.
19) View Boston Holiday Sip & Stroll
When: Sun. 12/7
Where: Back Bay
Cost: $29
Info: Purchase a ticket to the top of the Pru and enjoy $5 off admission on December 7 when Boston Women’s Market will be hosting a pop-up. Support over 20 women-owned businesses while taking in sweeping 360-degree views of the city, sipping on a holiday-themed drink, and listening to live music.
20) Ukrainian Art & Handicrafts Show and Sale
When: Sun. 12/7
Where: Newton
Cost: Free
Info: Celebrate Ukrainian culture and talent at this holiday market where all proceeds will be supporting frontline workers in Ukraine. Shop for handmade ceramics, wooden sculptures, and embroidered items by Ukrainian and Ukraine-American artisans.
21) Boston Hassle Holiday Flea Market
When: Sun. 12/7
Where: Cambridge
Cost: $2
Info: Check out the holiday pop-up of Boston Hassle Flea. Get ready to find the perfect gifts from over 85 small businesses while listening to live music, sipping on cozy drinks, and more. Connect with local artists and friends at this market.
22) Trident Booksellers Sip & Shop
When: Tue. 12/9
Where: Back Bay
Cost: Free
Info: The beloved Trident Booksellers & Café is hosting their annual Sip & Shop event. Enjoy complimentary tastings of hot apple cider and festive treats. Make some crafts, shop for books and knick-knacks, get personalized book recs, and more.
23) Roslindale Village Main Street Holiday Market
When: Thu. 12/11
Where: Roslindale
Cost: Free
Info: Join the Rozzie community for their holiday market where you can explore over 20 local vendors. There will be a live DJ, a performance by JP Honk, and plenty of holiday decor spanning Birch Street Plaza, the Emerald Society, and Sophia’s Grotto patio.
24) Fenway Holiday Party & Market
When: Fri. 12/12
Where: Fenway
Cost: $12.51+
Info: Stop by the Fenway Community Center for an evening of holiday cheer and community connection. With your ticket, you’ll get one complimentary drink. As you sip, shop from local art vendors, enjoy live music, and mingle with neighbors.
25) Black Business Holiday Marketplace
When: Fri. 12/12 - Sun. 12/14
Where: Harvard Square
Cost: Free
Info: Support local Black businesses this holiday season by checking out the Black Business Holiday Marketplace. There will be hand-crafted gifts and other fun goodies, as well as live entertainment and an opening night reception with live businesses. Shop for jewelry, soap, clothing, and more.
26) Station Street Studios Holiday Market
When: Saturdays and Sundays, starting Sat. 12/13 - Sun. 12/21
Where: Brookline
Cost: Free
Info: ArtsBrookline and Station Street Studios will be hosting their annual Holiday Market Open Studios. Meet and chat with local artists, shop for unique pieces, and learn more about their artistic processes as you roam through their gallery and studio spaces.
27) Boston Women’s Holiday Market at Night Shift Brewing
When: Sat. 12/13
Where: Everett
Cost: Free
Info: Grab a brew and get cozy at Night Shift Brewing where Boston Women’s Market will be hosting a holiday pop-up. Find unique, handmade gifts and sip on holiday-themed cocktails. Munch on some bites, paint some free ornaments, participate in an ugly sweater contest, and more.
28) 2nd Annual Holiday Maker Fair at Guild Hall
When: Sat. 12/13
Where: Cambridge
Cost: Free
Info: Guild Hall will be hosting their 2nd Annual Holiday Maker Fair. Get ready for an immersive afternoon of holiday festivities. Snap a pic with Santa, create your own ornaments, jewelry, and cards, and check out the virtual reality demo station. Plus, there will be combat robots, storytime in English and Russian, and other activities for the entire family.
When: Sat. 12/13
Where: South End
Cost: $10
Info: This holiday market honors tradition. Stop by this bazaar where you can meet makers who are upholding artistic practices from Indigenous communities and cultures from all over the world. There will be live music, demonstrations, storytelling, food, and more. Celebrate Indigenous resilience and talent this holiday season.
30) December Holiday Art Fair at Bow
When: Sat. 12/13
Where: Union Square
Cost: Free
Info: Throughout the year, Bow Market has been hosting a monthly Somerville Art Fair pop-up. This market is the grand finale where all nine artists will be showcasing their work. Celebrate art, community, and art where you can mix and mingle with the makers and other art-lovers while shopping small.
31) Canal District Kendall Winter Market
When: Sat. 12/13 - Sun. 12/14
Where: Kendall
Cost: Free
Info: The Canal District holiday pop-up is back for one weekend in the heart of Kendall Square. Shop from over 30 local businesses, catch 2 professional figure skating shows, ice skate for free, and make some crafts. There will be plenty of photo-ops with Santa, Elsa, and other wintry characters too.
When: Sun. 12/14
Where: Back Bay
Cost: $10
Info: New England Open Markets is hosting their 22nd annual holiday market at Fairmont Copley Plaza. Step into this historic building and shop from over 75 talented artists, designers, and culinary experts. There will be something for everyone at this local maker market.
33) Christmas Stroll at the Liberty Hotel
When: Sun. 12/14
Where: Beacon Hill
Cost: Free
Info: Stop by the Liberty Hotel and wander through the lobby full of the beautiful, locally famous upside-down Christmas trees that are, yes, dangling from the ceilings. As you explore, sip on a festive drink from the bar, munch on seasonal treats, and shop from local businesses.
34) Boston Harbor Distillery Holiday Sip & Shop
When: Sun. 12/14
Where: Dorchester
Cost: Free
Info: Enjoy some holiday shopping with a view of the Boston waterfront. Head to Boston Harbor Distillery where you can sip on some festive drinks while connecting with local vendors for some unique goodies. There will also be bottle engraving, merch, and other surprises.
35) Boston Women’s Holiday Market at Time Out Market
When: Sat. 12/20
Where: Fenway
Cost: Free
Info: Stop by Time Out Market for holiday drinks and bites. Then, complete your last-minute shopping and check out the Boston Women’s Market which will be hosting a holiday pop-up with plenty of small, women-owned businesses.
36) Winter Wishes Holiday Market
When: Sun. 12/21
Where: Hyde Park
Cost: Free
Info: Check out the Caribbean Street Market’s holiday pop-up: Winter Wishes at Roundhead Brewing. Sip on some brews and shop small all day from local businesses. There will be food, a free toy giveaway for families, and other fun activities for all.
FESTIVE RESTAURANTS & BARS
1) 10+ Festive Pop-Up Bars & Restaurants in Boston to Visit During the 2025 Holiday Season
When: December
Where: Boston & outside the city
Cost: Varies
Info: No one does holiday-themed drinks and food like Boston. Check out these local bars and restaurants that will be serving up holly jolly bevs and bites with a festive twist. Enjoy the holiday decor and ambiance on your night out.
2) Cozy Christmas Cabin at Hunter’s
When: Daily until early January
Where: Southie
Cost: Free admission; pay as you go
Info: Hidden in a cozy cabin restaurant is a festive upside-down Christmas tree, festive drinks, and Southern comfort food. Head to Hunter’s for all of your homey cravings and holiday cheer. Don’t miss their tree lighting on Wed. 12/3 for some live music too.
When: Daily until early January
Where: Charlestown
Cost: Free admission; pay as you go
Info: Enjoy Italian food and wonderful cocktails at one of the most beautiful restaurants in the city. Prime lines its windows with beautiful giant red-bowed wreaths every year. Step inside the breathtaking atmosphere and indulge in this fancy hideaway from the winter cold!
4) Avery Bar Chocolat: Hot Chocolate Table-Side Service at The Ritz
When: Every Saturday & Sunday, starting Sat. 11/29 until Sun. 12/28
Where: Downtown
Cost: $49
Info: Cozy up with a warm cup of hot cocoa by a fire. Head to the Ritz for an elevated service where you can munch on some decadent sweets and pastries while sipping on hot cocoa just the way you like it. Bonus tip: make your cocoa boozy for some extra festive fun!
5) Beacon Hill Books & Cafe Holiday Tea
When: Every Sunday & Monday, starting Sun. 12/1 until Mon. 12/30
Where: Beacon Hill
Cost: $75
Info: Cozy up this winter with a warm cup o’ tea. The quaint and cozy Beacon Hill Books & Cafe is hosting their Holiday Tea service. Enjoy fun-shaped biscuits, sweets, and savory treats. Then, explore the fun holiday decor throughout the floors of the store.
ICE-SKATING RINKS
1) The 11 Best Outdoor Ice Skating Rinks in Boston: Winter 2025
When: December
Where: Boston
Cost: Varies
Info: There are so many places to ice skate and feel the holiday spirit in and around Boston. See if you can hit each one of our favorite spots on this list before spring is here (the cold will be over before you know it!). Bundle up and get ready to glide all over the city.
HOLIDAY PERFORMANCES & MOVIES
1) Boston Ballet Presents Mikko Nissinen’s ‘The Nutcracker’
When: Daily until Sun. 12/28
Where: Theater District
Cost: $36+
Info: Boston Ballet presents its iconic ‘The Nutcracker’ performance to ring in the holiday season. A Boston winter isn’t complete without seeing these talented dancers take the stage to present this traditional holiday story. Come see the beautiful sets, costumes, and stage design, and leave with an unforgettable memory of this show.
2) 2025 Annual Dunster House Messiah Sing
When: Tue. 12/2
Where: Harvard Square
Cost: Free
Info: The Dunster House in Harvard Square will be hosting their annual live music holiday performance and you get to be an active participant. Join the Bach Society Orchestra and a guest conductor who will guide you in this community sing-along of this composition that was created in 1741. Enjoy light refreshments and mix and mingle with neighbors afterwards.
3) Isabella Stewart Gardner Museum: Holiday Music in the Courtyard
When: Wed. 12/3
Where: Fenway
Cost: $50
Info: Celebrate the holidays at the beautiful Isabella Stewart Gardner Museum. Explore the galleries after hours and watch a musical performance in the courtyard that will be bursting with colorful wintry blooms. Plus, you’ll have opportunities to sing along to some familiar carols as the Vox Vocal Ensemble and American Brass Quintet put on a show.
4) Final Figure Skating Show at the Oldest Indoor Ice Rink in the World
When: Wed. 12/3
Where: South End
Cost: $8-10
Info: Matthews Arena is the oldest indoor ice rink in the world, and it will be closing for renovations for an indefinite amount of time. Come visit before it takes a break from the public by catching an ice skating performance by the Northeastern University Figure Skating Team.
5) Holiday Pops at Symphony Hall
When: Select days, starting Thu. 12/4 until Wed. 12/24
Where: South End
Cost: $50
Info: Join the Boston Pops orchestra as they perform their Holiday Pops show, an annual Boston tradition. Enjoy classics like ‘Jingle Bells,’ ‘Sleigh Ride,’ and ‘The 12 Days of Christmas’ come alive on stage.
6) Boston Baroque: Handel’s Messiah
When: Fri. 12/5 & Sun. 12/7
Where: South End
Cost: $75
Info: Welcome the holiday season by catching this special performance of Handel’s ‘Messiah,’ a pivotal work in classical music that has been around since 1741. Watch a talented quartet from Boston Baroque perform on stage as the group’s assistant conductor makes his stage debut too.
When: Select days, starting Fri. 12/4 until Sun. 1/4
Where: Somerville
Cost: $35
Info: Come see the 18th season of ‘The Slutcracker.’ This show is a reimagined telling of ‘The Nutcracker’ that’s 18+ only. Cheer on the talented dancers as they perform this all-inclusive, body-positive, and absolutely hilarious burlesque show.
8) ‘Polar Express’ at CambridgeSide
When: Sat. 12/6
Where: Cambridge
Cost: Free
Info: A Christmas classic is the star of this community movie screening at CambridgeSide. Grab a bite to eat from one of the local vendors or a festive drink from the bars on-site and get cozy while watching the ‘Polar Express.’
When: Saturdays, starting 12/6 - 12/20
Where: Boston Common
Cost: Free
Info: MeetBoston has brought something new to the holiday season on the Common this year. For select Saturdays in December, you can venture outside and catch a special holiday-themed drone show in the night sky as it illuminates the gardens of the city. Catch your favorite characters and holiday symbols — all powered by new technology.
10) Charles Dickens’s ‘A Christmas Carol’
When: Select days, starting Sat. 12/6 until Tue. 12/23
Where: Theater District
Cost: $30+
Info: The beloved Commonwealth Shakespeare Company is back for their second annual production of 'A Christmas Carol.' One of Boston's most beloved groups, who produce Shakespeare on the Common, has created their own timeless adaptation of this famous holiday story, so be sure to grab a ticket and check it out.
When: Sat. 12/13 & Sun. 12/14
Where: Back Bay
Cost: $6.11+
Info: Make your way to the heart of Back Bay and step into Trinity Church Boston which will be illuminated with tons of candles. Participate in Candlelight Carols, a tradition that has been around since 1909, where you can sing holiday songs with the Trinity Church Boston Choir and local instrumentalists.
12) Anthony Williams’s ‘Urban Nutcracker’
When: Select days, starting Sat. 12/13 until Sun. 12/21
Where: Theater District
Cost: $29+
Info: Catch the 25th season of this contemporary retelling of the classic ‘Nutcracker’ story that features ballet, breakdance, flamenco, and jazz styles with local musicians. Head to the Boch Center Shubert Theatre where you can watch this performance take the stage that’s inspired by Boston landmarks too.
When: Tue. 12/16
Where: West End
Cost: $30+
Info: City Winery will be hosting ‘A Very Motown Christmas.’ Get ready for soulful rhythms, beautiful harmonies, and talented vocal performances from the Motown era, and enjoy a cozy night of music in a close-knit community setting to ring in the holiday season.
When: Wed. 12/17
Where: Back Bay
Cost: Free
Info: It isn’t a complete holiday season without singing the classic ‘Messiah’ piece. Join neighbors at the Cathedral Church of St. Paul where you can listen or participate in singing this piece. Chat with new friends after warming up those vocal cords with complimentary hot cocoa after the performance.
15) Holiday Drag Show at Aeronaut
When: Wed. 12/17
Where: Somerville
Cost: $15
Info: Head to Aeronaut for their monthly drag show with a holiday twist. Grab some drinks and cheer on talented drag performers who will be showcasing if they’re naughty or nice on the stage.
When: Thu. 12/18
Where: Back Bay
Cost: Free
Info: Have a laugh and enjoy this free screening of ‘Elf’ at the beloved Trident Booksellers & Cafe. Drinks and food will be available for purchase, so get cozy, bring your friends, or come solo and watch this holiday classic.
17) Naughty & Nice: Holiday Movie Night at Arts at the Armory
When: Fri. 12/19
Where: Somerville
Cost: $15
Info: Arts at the Armory will be hosting a holiday movie night with back-to-back screenings of holiday classics. Wear your ugliest sweater for a chance to win a prize, snack on popcorn and candy, and get ready to watch ‘Home Alone’ and ‘Die Hard.’
18) The Back Bay Chorale: A Boston Christmas
When: Fri. 12/19 & Sat. 12/20
Where: Back Bay
Cost: $32+
Info: Feel the spirit of the holiday season by joining the community and neighbors at the Back Bay Chorale’s annual holiday performance at Old South Church. Watch talented musicians sing alongside local brass, organ, and percussion players, and participate in some carols too.
19) Holiday Movie Night: ‘The Muppet Christmas Carol’
When: Sat. 12/20
Where: Union Square
Cost: $5
Info: Bring your friends and family for this all-ages movie night of ‘The Muppet Christmas Carol.’ Don’t forget to wear your best ugliest sweater for some fun prizes, enjoy some hot cocoa, and have a laugh at the cozy Upstairs at Bow location.
20) ‘A Christmas Carol’ at the Omni Parker House
When: Sun. 12/21
Where: Downtown
Cost: $35
Info: Enjoy a festival holiday reading of ‘A Christmas Carol’ at the Omni Parker House. With your ticket, you get a $10 voucher to the Bah Humbug Bar while you listen to elaborate storytime with vocals and a live violin.
21) Boston’s Big Band Christmas
When: Sun. 12/21
Where: West End
Cost: $25-45
Info: While Boston Ballet and Boston Pops produce some of the most iconic events during Boston’s holiday season, the 19-piece Compaq Big Band also has an exciting tradition that’s been around for the past six years. Come enjoy the sounds of the ‘Big Band Christmas’ performance featuring talented instrumentalists and vocalists.
22) Boston Pops: Elf in Concert
When: Sat. 12/27 & Sun. 12/28
Where: South End
Cost: $70+
Info: Join the Boston Pops as they perform one of their most iconic holiday traditions: ‘Elf’ in Concert. While this film is projected on the big screen, enjoy the sounds of the talented musicians as they play the score and music live for the audience.
23) Boston Pops: A Charlie Brown Christmas Live
When: Tue. 12/30
Where: South End
Cost: $73+
Info: Nothing screams Christmas without a visit from Charlie Brown. Celebrate the holiday season by catching a communal screening of ‘A Charlie Brown Christmas’ while the talented Boston Pops orchestra plays the score from the movie. Check out this seasonal Peanuts special.
FESTIVE EXPERIENCES
1) The Toy Shop at Hummingbird Books
When: Daily until Tue. 12/31
Where: Chestnut Hill
Cost: Free
Info: The Hummingbird Books bookshop always goes all out for the holiday season. Step into a life-sized gingerbread house where you can shop for knick-knacks, books, and more. On select days, you can even get your purchases gift-wrapped. Check out this local shop, add to your TBR, and explore this art installation.
2) All Aboard! Trains at Science Park Exhibit
When: Daily until Fri. 1/19
Where: West End
Cost: $33
Info: There’s a new exhibit in the Museum of Science. Go see the miniature versions of iconic Boston landscapes covered in snow. There will be mini trains, engaging activities, and other fun surprises.
When: Thu. 12/4
Where: Back Bay
Cost: Free
Info: Meet other booklovers and show off your favorite reads with new friends at The Stacks room of Trident Booksellers & Cafe. Grab a bite to eat, bring five books, and swap for five new ones for your TBR.
When: Thu. 12/4
Where: Downtown
Cost: $34
Info: Grab a ticket to the Volo Holiday Party where you can meet new friends. Enjoy a festive night with an open bar, light appetizers, raffles, and more. Come mix, mingle, and play some fun games to kick off the holiday season.
5) First Fridays: Wintry Mixer
When: Thu. 12/4
Where: Downtown
Cost: $40
Info: Check out the final ICA First Friday of the 2025 season. This party is themed ‘Wintry Mixer’ so come dressed in your best wintry wonderland outfits and get ready to dance to great music, make some art, explore the galleries, and meet some new friends.
6) Winter Garden at the Prudential Center
When: Thu. 12/4 - Thu. 12/18
Where: Back Bay
Cost: Free
Info: Head to the Pru for this new, interactive wintry art experience. The South Garden will be transformed into a sound and light installation. Reflective light sculptures will dance around with synchronized soundscapes as you roam around the garden.
7) Polar Pals Ice Sculpture Display
When: Fri. 12/5 - Sun. 12/7
Where: Kendall Square
Cost: Free
Info: New wintry friends are popping up at Danny Lewin Park. Say hello to the Peter Sea the Polar Bear and K.C. the Penguin ice sculptures who will be hanging out over the weekend. Don’t miss the opening party on 12/5 for some free cocoa and cookies to give them a warm welcome to the city.
When: Fridays & Saturdays, starting Fri. 12/5 until Sat. 12/27
Where: Seaport
Cost: $20
Info: Explore Boston this holiday season in a new light by walking the Freedom Trail. Tour guides will be dressed the festive part, so get excited to learn about the history of the city and different traditions while taking a stroll and visiting holiday trees, landmarks, and more.
When: Sat. 12/6
Where: Somerville
Cost: Free
Info: Get ready for a country night at the Arts at the Armory. There will be live music by the Talking Hearts and a 30-minute swing lesson by Boston’s very own Backout Country. Meet new friends and don’t forget your cowboy boots.
10) Winter Festival
When: Sat. 12/6
Where: Seaport
Cost: Free
Info: Massport is hosting a day-long wintry festival with a free holiday movie double feature of ‘Santa Claus’ and ‘Santa Claus 3.’ There will also be a makers market and sips and bites for kids and adults to enjoy. Don’t miss the tree lighting, Santa photo-ops, and other fun activities.
11) Loring Greenough Holiday Open House
When: Sat. 12/6
Where: Jamaica Plain
Cost: Free
Info: Stop by the Loring Greenough House this holiday season for a festive day of community connection. Learn about the stories of this historic home, make some crafts, watch a performance by the ‘Urban Nutcrackers’ dancers, and help trim the holiday tree on the grounds. There will be a mini beer garden, an art market, and more.
When: Sat. 12/6
Where: Dorchester
Cost: Free
Info: The Epiphany School will be hosting a winter wonderland festival for families in the city. Enjoy live music, face painting, holiday crafts, and more for everyone of all ages. Sip on hot cocoa, munch on some treats, and connect with neighbors.
13) Gingerbread Standard Construction
When: Saturdays, starting Sat. 12/6 - 12/20
Where: Fenway
Cost: $150
Info: It’s time for this annual holiday tradition at Eastern Standard Kitchen! With your ticket, you will get a freshly baked, fully constructed gingerbread house that you can decorate with tons of candy and decorating tools. This is a perfect holiday event for family and friends. Create the cookie house of your dreams with loved ones.
When: Select days, starting Sat. 12/6 - Tue. 12/30
Where: Charlestown
Cost: $5
Info: The winter village at Hood Park is making its grand return. Enjoy cozy ski gondolas, a giant illuminated castle, holiday treats, and a mini art market. Explore the grounds of this holiday activation while sipping on festive drinks and more.
15) Candlelit Labyrinth Walk: In Peace & Harmony
When: Sun. 12/7
Where: Rose Kennedy Greenway
Cost: Free
Info: Welcome the holiday season with this Greenway tradition at the Armenian Heritage Park. Enjoy a candlelight walk with neighbors in the labyrinth and stay for hot cocoa and sweet treats with new friends.
16) Holiday Edition Pottery Workshop
When: Tue. 12/9
Where: Cambridge
Cost: $75+
Info: Relax and get creative with this holiday-themed pottery workshop. Sip on a drink while learning how to pinch and mold your own clay pot or sculpture. Bring your friends or meet new ones as you create art.
17) Holiday Crafts & Filipino Food
When: Tue. 12/9
Where: Union Square
Cost: $30-40
Info: Maligayang Pasko! Come learn about Filipino culture and celebrate the holidays with a Filipino twist. Munch on crunchy lumpia, make your own ornament, relax with some coloring, and grow your community.
When: Thu. 12/11
Where: Southie
Cost: Free
Info: Make your way to Southie for a family-friendly holiday celebration outside by the water. Drink some cocoa, listen to live music, say hi to Santa, and play some games. There will be free books, complimentary pizza, and plenty of opportunities to get to know your neighbors.
19) 20s & 30s Ugly Sweater Social
When: Fri. 12/12
Where: Downtown
Cost: Free
Info: Meet new friends this holiday season by donning your ugliest, cringiest sweater at this 20s & 30s ugly sweater social. Mix and mingle in the festive Citizen M Hotel’s Swanky Lounge where there will be drinks, games, and food.
20) Ugly Sweater Party at Sam Adams
When: Fri. 12/12
Where: Jamaica Plain
Cost: Free
Info: Stop by Sam Adams Brewery for an ugly sweater holiday party. Take out those brightly colored, memeable sweaters and wear them with pride as you sip on festive, hearty brews and listen to live music with new friends.
21) Play Playe Game Night: Holiday Edition
When: Fri. 12/12
Where: Hyde Park
Cost: Free
Info: Check out Roundhead Brewing’s 2nd Annual Play Playe Game Night. Bring your friends or come solo to meet new ones, and sip on some brews while enjoying a night of community fun. There will be karaoke, board games, card battles, and a live DJ.
22) Longfellow Holiday Open House
When: Fri. 12/12
Where: Cambridge
Cost: Free
Info: Step into a piece of history during the annual Longfellow Holiday Open House. Take a tour of George Washington’s headquarters which will also be decorated for the holidays. Enjoy storytimes and access to special seasonal objects from the museum’s collection too.
When: Fri. 12/12 - Sat. 12/13
Where: Downtown
Cost: $45.99
Info: Explore the WNDR Museum after hours during this special holiday event. Wander through the festive exhibits with live music and light installations. You can also make your own holiday fragrance, munch on a complimentary cinnamon roll, and sip on some warm cider.
24) Boston Frozen Fire Festival 2025
When: Fri. 12/12 - Sat. 12/13
Where: Charlestown
Cost: Free
Info: For the first time ever, the Frozen Fire Festival will be making its Boston debut. Head to the Anchor for a holiday market, curling lanes, a s’mores & chocolate bar, and of course, fire and ice installations. There will be live music, fire & cirque performances, and other fun surprises.
25) Gingerbread House Building Contest
When: Sat. 12/13
Where: Cambridge Crossing
Cost: $0-25
Info: Cheer on others as they build a gingerbread house or make your own at Lamplighter Brewing CX. Get in the holiday spirit while sipping on some brews and building and decorating your very own gingerbread house with icing and candy.
26) Sensual Saturday: Bachata Holiday Party
When: Sat. 12/13
Where: Cambridge Crossing
Cost: $15-20
Info: Show off your dance moves and learn new ones at this weekly dance social with a holiday twist. Wear red and white to get in the festive spirit. Then, get ready to learn how to bachata and then practice the moves with new friends.
27) 29th Annual Ciclismo Classico Jingle Ride
When: Sun. 12/14
Where: Arlington
Cost: $0-25
Info: Get ready to sweat in this winter cold and participate in one of the longest-running holiday sporting events in Boston. Wear your best holiday costume, get those singing voices ready, and enjoy 18.5 miles of cycling with new friends. Don’t worry, you’ll be able to stop and rest for a bit as you spread some holiday cheer for passersby!
28) Gingerbread House Decorating at Aeronaut
When: Sun. 12/14
Where: Somerville
Cost: $20
Info: Grab your ticket and join the gingerbread house decorating social at Aeronaut. Sip on some brews and bring a friend to cover your own gingerbread house in icing and candy. This is a fun and creative way to celebrate the holiday season.
29) Holiday Lights Stroll + Ornament Making Singles Social
When: Tue. 12/16
Where: Fenway
Cost: $25
Info: Looking to meet new friends? Join this community social where you can explore Boston and all of its holiday lights. Then, get cozy and warm up at Mighty Squirrel Fenway where you can chat with others, make some ornaments, and more.
When: Thu. 12/18
Where: Fenway
Cost: $5
Info: For this Third Thursday at the MFA, participants can enjoy an entire after-hours museum party dedicated to Hanukkah. Enjoy art-making, a menorah lighting, live music, dining specials, and spotlight tours of special works that highlight Jewish life.
31) 20s & 30s Let’s Explore Boston’s Holiday Lights
When: Sat. 12/20
Where: Fenway
Cost: Free
Info: Bundle up and brave the cold to explore the city. Meet new friends and connect with other 20 and 30-somethings as you stroll around Boston, making your way from Comm Ave, the Commons, and Downtown Crossing to Quincy Market and the North End Trellis. Then, keep the party going at a bar where you can continue chatting with others.
When: Sat. 12/20
Where: Back Bay
Cost: $10
Info: Enjoy a cozy night in at Trident Booksellers & Cafe where you can play several rounds of Bingo to win some prizes. There will be food and drinks available for purchase, and you can mix and mingle with new friends.
33) Milk & Cookies Cake Decorating Class
When: Sun. 12/21
Where: Cambridge
Cost: $50
Info: This fun holiday event is perfect for those with a sweet tooth. Have fun learning how to decorate your own cake and express yourself with icing, mini cookies, sparkly sprinkles, and more. Then, take your dessert home and share your sugary creation (or not) with friends.
OTHER FUN EVENTS
1) Harvard Art Museums at Night
When: Thu. 12/4
Where: Harvard Square
Cost: Free
Info: Your favorite free, after-hours museum party is back. Head to the Harvard Art Museums for an evening of art-making and exploration. Stroll through the galleries, dance to the tunes of a live DJ, and enjoy a special holiday discount at the gift shop.
2) Full Moon Yoga @ the Museum of Modern Renaissance
When: Fri. 12/5
Where: Seaport
Cost: $40
Info: Relax and reset at Bulldog Flow’s full moon yoga. Marvel at the beautiful walls of the Museum of Modern Renaissance while stretching your body and practicing different poses. Then, enjoy a crystal bowl soundscape to close off the lesson.
When: Fri. 12/5
Where: Roslindale
Cost: $10
Info: Dress your best and get ready to show off your dance moves at this community social. There will be a live 9-member jazz ensemble that will be playing roaring tunes. Plus, you can enjoy a swing dance workshop, cocktails, and other fun swing era-themed activities.
4) Crafts & Cocktails: Champagne Flute Painting
When: Sat. 12/13
Where: Back Bay
Cost: $12
Info: Stop by Trident Booksellers & Cafe and enjoy a cozy crafting night. You’ll have one glass champagne flute that you can paint and decorate (perfect to ring in the upcoming new year) while watching ‘While You Were Sleeping!’. Food and drinks will be available for purchase too.
5) fruitstand presents: C*ntstruction
When: Sat. 12/13
Where: Cambridge
Cost: $10
Info: The cold weather never stopped anyone from partying. Join fruitstand during their December queer nightlife event where you’ll get to dance nonstop under the disco light. Come dressed in your favorite safety and construction gear too.
6) Boston Tea Party 252nd Anniversary Commemoration
When: Sat. 12/13
Where: Downtown
Cost: $25+
Info: Celebrate the 252nd anniversary of the Boston Tea Party. There will be historic reenactments, interactive storytelling, and free admission to different historic sites included with your ticket. Come honor history with friends and family.
7) Sunday Morning Yoga with Live Piano @ the Museum of Modern Renaissance
When: Sun. 12/21
Where: Somerville
Cost: $35
Info: Enjoy a holiday edition of interactive yoga at the beautiful Museum of Modern Renaissance. Relax with a guided yoga practice by Bulldog Flow yoga that’s accompanied by a pianist who will be playing holiday songs on the piano.
8) The Darkest Night - A Bookish Solstice
When: Sun. 12/21
Where: Jamaica Plain
Cost: $15
Info: Winter Solstice, the longest night of the year, is upon us. Head to the Loring Greenough House with other bookish people and authors who will be telling ghost stories from their favorite haunted holiday tales.
When: Sat. 12/27
Where: Boston Public Garden
Cost: Free
Info: Participate in this monthly gathering with master florists all the way from Belgium and talented local guest designers at the Boston Public Garden. There will be mini demos, workshops, and informational talks. Come learn about seasonal blooms with new friends.
10) Boston Common Frog Pond Skating Spectacular
When: Wed. 12/31
Where: Boston Common
Cost: Free
Info: It’s the most magical way to say goodbye to 2025. Cheer on national and international competitive figure skaters as they show off their talents on the Frog Pond ice in the heart of the city.
When: Wed. 12/31
Where: Boston
Cost: Free
Info: Boston knows how to welcome the new year. Explore the city by enjoying an ice sculpture stroll across different neighborhoods, music and live performances at City Hall Plaza, and a beautiful fireworks display along the Harbor.
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