110 things to do in Boston for $10 or less: October 2025
When:
Wednesday, Oct 01, 2025 8:00a -
Friday, Oct 31, 2025 11:30p
Wednesday, Oct 01, 2025 8:00a -
Friday, Oct 31, 2025 11:30p
Where:
Boston
Surrounding Areas
Boston, MA
Admission:
$0-10
Categories:
Art, Date Idea, Drinks, Festivals & Fairs, Food, Games, Good for Groups, History, Kid Friendly, LGBTQ+, Meetup, Movies, Music, Nature, Nightlife, Party, Pet Friendly, Photoworthy, Rainy Day Ideas, Seasonal, Shopping, Shows, Social Good, Sports & Active Life
Happy fall, my Boston friends. Spooky season is upon us! Get ready for fall foliage, apple cider donuts & apple-picking, pumpkin spice lattes & pumpkin patches, and Halloween decorations & experiences all month long. Here’s your guide to all things cheap and free to make the most of October this year.
by Yelena Nicolle Salvador
1) ‘Harry Potter and the Prisoner of Azkaban’ at Hood Park
When: Wed. 10/1
Where: Charlestown
Cost: Free
Info: Kick off spooky season by heading to the final movie night at Hood Park. Enjoy a free screening of the third Harry Potter movie with free popcorn, candy, and bevs. Bring a blanket and enjoy a flick under the stars.
2) Watercolor Workshop at Lyrik
When: Wed. 10/1
Where: Back Bay
Cost: Free
Info: Looking for a mid-week pick-me-up? Take a break with the autumn breeze while painting with watercolors. Enjoy some preprinted illustrations that you can make your own while relaxing with some art.
3) International Moves and Food
When: Wednesdays, 10/1 & 10/8
Where: Charles River Esplanade
Cost: Free
Info: Head to the Esplanade for this fun series with the Boston Dance Alliance. Learn steps to cultural dances with friendly instructors right along the water. Then, celebrate with neighbors with complimentary food and beverages from a local restaurant based on that week’s cultural inspiration.
When: Wednesdays, 10/1 & 10/8
Where: Kendall Square
Cost: Free
Info: Catch a Halloween movie with great drinks at Saguaro Garden Bar before it closes for the season. Get cozy with a mocktail (or you can make it dirty) and enjoy a flick like ‘Hocus Pocus’ under the stars.
5) Watch Wednesdays at the Anchor
When: Wednesdays, starting 10/1 - 10/29
Where: Charlestown
Cost: Free
Info: Cross the river and grab a beverage right along the water with the Boston skyline as your backdrop. Then, enjoy free movie screenings like ‘Princess Bride,’ ‘Ghostbusters,’ and ‘Hocus Pocus.’
6) Taylor Swift: The Life of a Showgirl Album Release Party at Lou's
When: Thu. 10/2
Where: Harvard Square
Cost: Free
Info: Get ready for Tay’s new album release with your Swiftie besties. Head to the new Harvard Square restaurant, Lou’s, where you can enjoy the ambiance and a drink while listening to a DJ spin your favorite songs from across the eras. Then, get ready for a full listen through when the new album drops at midnight.
7) 20s & 30s Tacos and Drinks Social at Naco Taco
When: Thu. 10/2
Where: Central Square
Cost: Free
Info: Join 20 and 30-somethings at this social where you can meet new friends and grow your community. Naco Taco is a local fave, so come hungry and enjoy chips & salsa, $4 tacos, and some margs while you mix and mingle.
8) Pints & Purls: Knitting at Night Shift on the Greenway
When: Thu. 10/2
Where: Rose Kennedy Greenway
Cost: Free
Info: Relax as the week begins to wind down right on the Greenway with Boston Fiber Company. No experience is necessary, so come learn a new skill while you learn the basics of knitting at this class. Sip on a beer and meet new friends at this meet-up. All levels are welcome.
When: Thu. 10/2 & Sat. 10/4
Where: Back Bay
Cost: $7-10
Info: In honor of Taylor’s new album drop, Trident Booksellers & Cafe is hosting your favorite trivia night with a twist: Taylor Swift-themed! Bring your friends, grab a bite to eat, and test your Swiftie knowledge.
10) Thursdays on the Lawn at the Loring Greenough House
When: Thursdays, starting 10/2 - 10/30
Where: Jamaica Plain
Cost: Free
Info: It’s the final month of one of the community nights around the city. Thursdays on the Lawn are the perfect way to kick of your weekends early. Enjoy a bev at the beer garden, bring a picnic, explore the grounds of the house, and try out some new food from one of the pop-up food trucks.
11) Taylor Takeover at CambridgeSide
When: Thu. 10/2 - Fri. 10/3
Where: Cambridge
Cost: Free
Info: CambridgeSide is going all out in anticipation of Taylor’s new album drop. Sip on special-themed cocktails, play some Taylor trivia on Thursday, and enjoy a listening party on Friday with a bracelet-making and makeup station.
12) Fall Festival on the Greenway
When: Fri. 10/3
Where: Rose Kennedy Greenway
Cost: Free
Info: Welcome fall with this part on the Greenway. Get ready for food trucks, an art market, DJ tunes, glow-in-the-dark mini golf, and even an inflatable obstacle course. In true autumn spirit, you’ll be able to decorate pumpkins and catch a free screening of ‘The Addams Family’ (1991) outdoors.
13) TSwift Album Release Party: The Life of a Showgirl Listening Experience
When: Fri. 10/3
Where: Union Square
Cost: Free
Info: The wait is over — Taylor’s new album dropped and it’s time to celebrate. Come dressed in your favorite era or as your inner showgirl and head to Remnant Brewing at Bow. Get there early for a chance at a complimentary party bag, and get ready to sing and dance.
14) Taylor Swift Listening Party
When: Fri. 10/3
Where: Fenway
Cost: Free
Info: Head to Time Out for the ultimate Swiftie listening party. Enjoy Taylor-inspired drinks, a DJ spinning tunes across the eras, and food specials. Participate in the Taylor Look-Alike contest and come early for a complimentary friendship kit.
15) The Life of a Showdog: A TS12 Pup-Friendly Party
When: Fri. 10/3
Where: Everett
Cost: Free
Info: Park-9 Dog Bar is hosting a pup-friendly Swiftie party in honor of album 12 dropping. Sip on some brews, test your knowledge with some Taylor trivia, listen to Tay all night, and meet new animal-loving friends.
16) Fall Movie Nights on the Greenway
When: Fridays, starting 10/3 - 10/24
Where: Rose Kennedy Greenway
Cost: Free
Info: Enjoy free weekly outdoor movie screenings on the Greenway to celebrate fall. There will be complimentary popcorn and candy, food trucks on-site, and free blankets to rent. Catch your favorite fall flicks like ‘Goosebumps,’ ‘Twilight,’ and ‘Halloweentown.’
17) Fall Festival @ The Yard Beachmont Square
When: Sat. 10/4
Where: Revere
Cost: Free
Info: The annual Revere Fall Festival will be hosted at a new location this year: Beachmont Square. Shop from an art market, listen to live music all day, explore the new Twisted Fate brewery, and munch on snacks from different food trucks. There will be games, roaming entertainment, and more.
18) Fall Fest at Kendall/MIT Open Space
When: Sat. 10/4
Where: Kendall Square
Cost: Free
Info: Welcome the beginning of autumn at Kendall/MIT Open Space’s fall party. Play some lawn games, make some art, grab a sweet treat, and listen to some live music by the Fly By Brass Band.
When: Sat. 10/4
Where: Dorchester
Cost: Free
Info: The Harvest Moon is here — celebrate Vietnamese culture and its traditions at Tết Trung Thu, the Mid-Autumn Festival. Enjoy cultural performances, lantern displays, food and art from different vendors, and so much more.
When: Sat. 10/4
Where: Seaport
Cost: Free
Info: The Lawn on D is hosting their annual fall festival for all ages. Bring your friends and family for this party featuring face painting, caricature and balloon artists, live animals, and more. Grab a drink and enjoy the fun.
21) 9th Annual Quincy’s Food Truck & Music Festival
When: Sat. 10/4
Where: Quincy
Cost: Free
Info: Check out the 9th Annual Food Truck & Music Festival in Quincy. Get ready for delicious eats from over 30 food and dessert trucks and a whole bunch of bands who will be playing all day. Play some lawn games and hang out with friends at this outdoor party.
22) MassQ Ball
When: Sat. 10/4
Where: Arnold Arboretum
Cost: Free
Info: Celebrate the creative talents of Boston’s communities of color at the MassQ Ball. Bring your friends and family, connect with art, and enjoy a full day of live music, dance performances, spoken word and poetry, and visual art installations.
When: Sat. 10/4
Where: Medford
Cost: Free
Info: Head to the Mystic River for a neighborhood party to honor the river herring. Mystic Ribert Artist in Residence, Andres Duarte, will be presenting a free outdoor art show featuring live music, theatrical dance, lights and visuals, and more in the heart of Macdonald Park.
24) Nichols House Museum Autumn Community Day
When: Sat. 10/4
Where: Beacon Hill
Cost: Free
Info: Explore the historic Nichols House Museum at this free community day with a guided tour. Learn about the history of the powerful Nichols women, watch a wordworking demonstration, and connect with neighbors.
25) Boston Public Library Sale
When: Sat. 10/4
Where: Back Bay
Cost: Free
Info: Don’t miss the BPL fall book sale. Enjoy $1-2 hardcover and softcover books, CDs, DVDs, and other fun treasures. Stock up for your cozy fall and winter reading needs, and donate whatever’s collecting dust in your homes too. Plus, proceeds support community programming around the city.
26) Magical Musical Mystery Bike Ride
When: Sat. 10/4
Where: Allston
Cost: Free
Info: Meet new friends at this local cycling community get-together. Enjoy a mostly flat, ~15-mile cruise on your bike while stopping for two dance party pop-ups along the route featuring local DJs. Soak up autumn views and public art in the city at this party.
27) CollegeFest
When: Sat. 10/4
Where: Fenway
Cost: Free
Info: Are you a college student in the area? Check out this free festival where you can meet new friends, grab free swag, connect with vendors and brands, and so much more. Don’t forget to bring your ID to join the fun.
When: Saturdays, starting 10/4 - 10/25
Where: Fenway
Cost: Free
Info: It’s the final month of Boston Open Market 2025. Shop from local artists while enjoying the fresh air before it gets too cold. Don’t miss the season closer: the 22nd Annual Halloween Market where you can shop for spooky goodies right next to the Public Garden.
29) 26th Annual Roxbury Open Studios Art Festival
When: Sat. 10/4 - Sun. 10/5
Where: Roxbury
Cost: Free
Info: Explore Roxbury’s imaginative art scene at the 26th Annual Open Studios event. Head to the Bolling Building where you can visit artists in residence. Check out their studios and connect with creators as they share their works.
30) Huge Outdoor Vintage Clothing Thrift Festival
When: Sat. 10/4 - Sun. 10/5
Where: Charlestown
Cost: Free
Info: Select Markets is bringing one of the biggest vintage markets to Hood Park. At this two-day event, you can shop for treasures from over 60 vendors. There will be free drinks, food from pop-up food trucks, $10 piles, music, and so much more.
31) Fenway ACKtoberfest at Cisco Brewers
When: Sat. 10/4 - Sun. 10/5
Where: Fenway
Cost: Free
Info: Oktoberfest season is winding down, but there are still some celebrations to check out. Head to Cisco in Fenway where you can listen to live music, watch a lederhosen and dirndl fashion showdown, and participate in stein-holding, brat tossing, and chocolate cake eating competitions.
32) Faneuil Hall Finery Fashion Festival
When: Sat. 10/4 - Sun. 10/5
Where: Downtown
Cost: Free
Info: The organizers behind the Brighton Bazaar are brewing up something new this season – the first-ever Finery Fashion Festival. Check out the old Uniqlo space in Quincy Market and shop from local vendors and artists for jewelry and clothes.
When: Sat. 10/4 - Sun. 10/5
Where: Fenway
Cost: Free
Info: Head to Time Out for two days of the Blair B*tch Project, a Halloween party & concert that provides a platform for female DJs, artists, and entertainers. Grab a bite and a cocktail, and get ready to jam out to Boston’s best female singer-songwriters and DJs.
When: Saturdays & Sundays (last Sun. of the season is 10/12), starting Sat. 10/4 - Sat. 10/25
Where: Rose Kennedy Greenway
Cost: Free
Info: Don’t miss the final few weekends of the Greenway Artisan Market this year. Shop from local artists, find the perfect gift for yourself or a loved one, and take a calming stroll along the Rose Kennedy Greenway before it gets too cold.
35) Night Shift Brewing’s Oktoberfest
When: Sun. 10/5
Where: Everett
Cost: Free
Info: The Night Shift Brewing Taproom is hosting one of the final Oktoberfest celebrations in the city. Come early for a chance at a free t-shirt for tie-dyeing. Build your own pretzel necklace, drink some brews, listen to live music, and participate in stein-holding competitions at this party.
36) Turkic World Nomadic & Cultural Festival
When: Sun. 10/5
Where: Cambridge
Cost: Free
Info: Learn about Turkic culture and traditions at this international festival in Cambridge. There will be music and dance performances, pop-ups serving Turkic delicacies, and kid-friendly games and activities.
37) Wicked Comic Con
When: Sun. 10/5
Where: Seaport
Cost: Free
Info: Check out the original Boston Comic Con where you’ll get to explore all things comics. Enjoy a full day of connection where you can shop for collectible merch, listen to talks featuring DC and Marvel comic book creators, and learn about local artists too.
38) Harvest Mixer
When: Sun. 10/5
Where: Dorchester
Cost: Free
Info: Head to Tavolo in Dorchester for the Harvest Mixer, a community meet-up where you can connect with neighbors and meet friends. Enjoy food, lawn games, raffles, and more.
When: Sundays, starting 10/5 - 10/26
Where: South End
Cost: Free
Info: It’s the final month of the 2025 SoWa Open Market. Enjoy the sweater weather while shopping from talented artists and local vendors. Grab a scrumptious bite or a refreshing drink from a food truck, roam the studios in SoWa, and play some lawn games too.
40) The Dating Game with Boston B-Side at Aeronaut
When: Mon. 10/6
Where: Somerville
Cost: Free
Info: Join B-Side and Aeronaut for this fun evening of a live dating show. Grab a drink and watch 16 bachelors and bachelorettes find romance on the main stage. Have a laugh, hang out with friends, and watch people find love in the city.
41) Hooks & Books
When: Tue. 10/7
Where: Back Bay
Cost: Free
Info: Spend a cozy evening at the beloved Trident Booksellers & Cafe with some crafting and reading. Make some new friends, bring a work in progress or a current book, and relax at this monthly meet-up.
42) Seaport Sketch
When: Tuesdays, 10/7 & 10/21
Where: Seaport
Cost: Free
Info: Learn some new art skills and meet new friends at this bi-weekly, complimentary art lesson at the Superette Courtyard. Enjoy guided lessons featuring easy drawing exercises with local artists and live music.
43) HONK! Festival of Activist Street Bands 2025
When: Thu. 10/9 - Sun. 10/12
Where: Charlestown
Cost: Free
Info: The beloved local activist band, HONK!, is hosting four days of outdoor band concerts. Connect with the community, dance to live music tunes, and stand in solidarity with local and global causes.
44) Color Flows on Winter Street
When: Sat. 10/11 - Sun. 11/16
Where: Downtown Crossing
Cost: Free
Info: Downtown Crossing is hosting a new multi-week public art activation. Enjoy live music, games, food pop-ups, and other family-friendly activities. Winter Street will be bursting with color and new life this fall.
45) Spooky Saturday at Urban Park
When: Sat. 10/11
Where: Kendall Square
Cost: Free
Info: Stop by the Urban Park roof garden for their annual Spooky Saturday party. Listen to DJ tunes, get your face painted (no matter how old you are), and get cozy while watching ‘Scooby Doo’ outdoors. There will be complimentary popcorn and beverages available for purchase while you enjoy this flick under the stars.
46) The Sanderson Sisters’ Drag Brunch & Bingo
When: Sat. 10/11
Where: Fenway
Cost: Free
Info: It’s hocus pocus season. Grab a themed cocktail and a bite to eat from Time Out while playing some witch-themed bingo. There will be drag performances, prizes, and a whole lot of wicked fun.
47) Color Flows Vintage Market
When: Sat. 10/11
Where: Downtown Crossing
Cost: Free
Info: Select Markets is hosting an outdoor vintage market as part of Downtown Boston’s newest activation: Color Flows. Shop for new treasures, grab a drink from the beer garden, listen to DJ tunes, and snag a snack from one of the food trucks.
When: Sat. 10/11
Where: Roxbury
Cost: Free
Info: Head to the Shirley-Eustis House for Boston’s very own apple festival. Make some crafts, enjoy complimentary cider donuts and popcorn, learn about the process of apple pressing, and grab a brew at the pop-up beer garden.
49) Diwali in Boston
When: Sat. 10/11
Where: Downtown
Cost: Free
Info: Join the India Society of Worcester at Quincy Market for a Festival of Lights celebration. There will be Rangoli art demonstrations, music and dance performances, and other family-friendly activities for Diwali.
When: Sat. 10/11
Where: Somerville
Cost: Free
Info: Celebrate Oktoberfest with Club Volo at Assembly Row. Play some pickleball, volleyball, cornhole, and lawn games while meeting new friends. There will be stein-holding competitions, plenty of brews and other fun bevs, and some fun giveaways.
51) Boston Women’s Market at Assembly Row
When: Sat. 10/11
Where: Somerville
Cost: Free
Info: Make your home extra cozy for fall with a new purchase from the Boston Women’s Market pop-up at Assembly Row. Grab a cozy candle, comforting treats, handmade accessories, and more.
52) Apple Booze Bash
When: Sat. 10/11
Where: Everett
Cost: Free
Info: It’s time for the 7th Annual Apple Booze Bash at Short Path Distillery. Enjoy live music, fall cocktails and cider flights, food pop-ups, and more. Check out the cafe for cozy lattes and other warm bevs.
53) Brewing Connections: Coming Out Day
When: Sat. 10/11
Where: Downtown
Cost: Free
Info: Celebrate National Coming Out Day with new friends at Brewing Connections, an intergenerational queer cafe. Meet people in the community, share stories, and connect over a warm cup of coffee, donuts, and fresh fruit.
54) ‘Avatar: The Last Airbender’ Trivia
When: Sat. 10/11
Where: Back Bay
Cost: $7-10
Info: Represent your element at this fun trivia night by Trident Booksellers & Cafe. Brush up on all things ‘Avatar: The Last Airbender’ and ‘The Legend of Korra’ and overthrow the fire nation. You can grab a bite to eat and meet new friends at this game night.
When: Sat. 10/11
Where: Rose Kennedy Greenway
Cost: Free
Info: Get your body movin’ at one of Boston’s oldest public dance events. Learn some tango moves from a Dance Union teacher and then meet new friends while social dancing to music the rest of the night.
56) How Bazaar: Wicked Weird & Witchy Wares
When: Sat. 10/11 - Sun. 10/12
Where: Brighton
Cost: Free
Info: The annual How Bazaar: Wicked Weird & Witched Wares market is back this season to bring you spooky goods. Make your way to the Brighton Elks Lodge and shop for handmade goodies, vintage clothes, vinyl, and more while listening to DJ tunes.
57) $5 Ferry Weekend
When: Sat. 10/11 - Mon. 10/13
Where: Boston Harbor Islands
Cost: $5
Info: Close out the 2025 ferry season with $5 rides during the long weekend. Visit Spectacle Island or Peddocks Island for a picnic, a stroll, and beautiful skyline views of the city. This is your last chance to visit the Boston Harbor Islands until next year.
58) 46th Annual Harvard Square Oktoberfest
When: Sun. 10/12
Where: Harvard Square
Cost: Free
Info: Don’t miss one of the most iconic annual events in Harvard Square: Oktoberfest! Get ready for a jam-packed day full of live music, international food vendors, multiple beer gardens, a craft and vendor market, and so much more.
When: Sun. 10/12
Where: Fenway
Cost: Free
Info: Grab your pups and your other four-legged friends and dress them in their best costumes. Bring them to Time Out for a Halloween party featuring a treat bar, a bandana station, a pup-friendly menu, and more.
60) Isabella Stewart Gardner Museum: Free Admission on Indigenous Peoples’ Day
When: Mon. 10/13
Where: Fenway
Cost: Free
Info: Enjoy free admission to the Isabella Stewart Gardner Museum on Indigenous Peoples’ Day. There will be art-making, storytelling, live music, and more. Explore the galleries, the current flora on display in the courtyard, and learn about Indigenous traditions.
61) MFA: Free Admission on Indigenous Peoples’ Day
When: Mon. 10/13
Where: Fenway
Cost: Free
Info: The MFA is offering free admission on Indigenous Peoples’ Day. Learn about the art on display with a guided tour, make some art, watch some cultural demonstrations featuring Indigenous artistry and storytelling, and listen to live music.
62) 2025 Opening Our Doors Day
When: Mon. 10/13
Where: Fenway
Cost: Free
Info: Join the Fenway community for the 24th Annual Opening Our Doors Day. There will be cultural experiences, art, and performances all across the Fenway/Longwood area. Check out the Fenway Studios, the Huntington Theatre, the Mary Baker Eddy Library, and other locations for creative programming.
63) Harvard Museums: Free Admission on Indigenous Peoples’ Day
When: Mon. 10/13
Where: Harvard Square
Cost: Free
Info: Visit the Harvard Museums of Science & Culture, including the Peabody Museum of Archaeology & Ethnology and the Harvard Museum of Natural History, for free on Indigenous Peoples’ Day. There will be tours, gallery talks, art-making, live music, and more across the different locations.
64) ICA Boston: Free Admission on Indigenous Peoples’ Day
When: Mon. 10/13
Where: Seaport
Cost: Free
Info: Make your way to the ICA which will be offering free admission on Indigenous Peoples’ Day. Explore the contemporary art galleries, enjoy waterfront views of the harbor, and get a first look at the newest exhibit, ‘An Indigenous Present.’
When: Mon. 10/13
Where: Allston
Cost: Free
Info: Join Wicked VHS for their monthly double feature. This month, you can meet new friends and soak up spooky season at The Model with a screening of ‘Fright Night’ and ‘The Exorcist.’
66) Coolidge @ the Speedway: ‘I Know What You Did Last Summer’
When: Wed. 10/15
Where: Brighton
Cost: Free
Info: Close out the 2025 season of Coolidge @ the Speedway with a free screening of ‘I Know What You Did Last Summer.’ Grab a brew from Notch and a bite to eat from one of the restaurants and say goodbye to summer.
67) $5 Third Thursday at the MFA
When: Thu. 10/16
Where: Fenway
Cost: $5
Info: On the third Thursday of the month, you can enjoy $5 admission to the MFA (a steal of a deal since entry is usually $30). Walk through the galleries, make some art, listen to live music, and snag an iconic hand-drawn portrait from Nick Shea.
68) The Head of the Charles Regatta 2025
When: Thu. 10/16 - Sun. 10/19
Where: Cambridge
Cost: Free
Info: The Charles Regatta is an annual iconic Boston event that you don’t want to miss. Watch athletes compete on the Charles during this rowing competition. Cheer them on along the river, grab a bite to eat from a food truck, and shop from local vendors too.
69) 17th Boston Asian American Film Festival
When: Thu. 10/16 - Sun. 10/26
Where: Downtown
Cost: $5+
Info: Enjoy Asian American storytelling during the 17th Annual Boston Asian American Film Festival. Grab a ticket to different movies and short films, listen to talks by filmmakers, and enjoy the ambiance of the Brattle Theatre and the Emerson Paramount Center.
70) Play It by Fear
When: Fri. 10/17
Where: Seaport
Cost: Free
Info: Seaport is hosting a spooky bash at The Rocks. Join Castle Island Brewing and Seaport for a fun party featuring live music, a vendor market, tarot card readings, boozy brews, and sweet treats.
71) ‘Hotel Transylvania’ at CambridgeSide
When: Fri. 10/17
Where: East Cambridge
Cost: Free
Info: Get cozy at the food court of CambridgeSide with delicious food options and some drinks if you wish. There will be fun activities for all before the flick begins. Then, find a spot and enjoy the feel-good, fall-themed movie ‘Hotel Transylvania.’
When: Fri. 10/17 - Sun. 10/19
Where: Seaport
Cost: Free
Info: A weekend full of art is coming to Fort Point. Check out the annual Fort Point Open Studios where you can connect with artists and performers at the historic waterfront warehouses. Listen to live music, check out the galleries, visit the pop-up exhibits, and mingle with other art-lovers at this event.
73) Open Streets 2025: Mattapan
When: Sat. 10/18
Where: Mattapan
Cost: Free
Info: The second-to-last Open Streets Boston of 2025 will be hosted in Mattapan this month. Enjoy a sweater weather stroll along the streets of the neighborhood, connect with ocal businesses, meet your neighbors, listen to live music, and so much more.
74) SpicetoberFest: Spice. Culture. Food.
When: Sat. 10/18
Where: City Hall Plaza
Cost: Free
Info: Check out the first-ever SpicetoberFest at City Hall Plaza. Celebrate the city and its diverse cultural and culinary influences. Meet 40 vendors, farmers, and exhibitors; try out hot sauces and peppers; watch a comedy show; and enjoy culinary demos throughout the evening.
75) Mushroom Fest at Bow Market
When: Sat. 10/18
Where: Union Square
Cost: Free
Info: Have a fun time at this fungi festival at Bow Market. Shop for some mushrooms and mushroom-related products, learn about different kinds of mushrooms, and chat with other mushroom lovers. There will be food specials, demos, and other fun activities.
76) 20s & 30s Halloween Party at Scorpion Bar
When: Sat. 10/18
Where: Seaport
Cost: Free
Info: Halloween is coming early to the Scorpion Bar. Come dressed in your best costume and meet other 20 and 30-somethings in the area. Make new friends, dance to DJ tunes, and enjoy this spooky party in the heart of Seaport.
77) Time Out Market Boston Cider Fest
When: Sat. 10/18
Where: Fenway
Cost: Free
Info: Nothing screams fall like a refreshing cider. Head to Time Out for this festival that celebrates this apple-licious drink. Sample ciders from different cideries across New England and enjoy food specials while listening to DJ tunes.
78) Left of the Charles: Music Festival & Bazaar
When: Sat. 10/18 - Sun. 10/19
Where: Brighton
Cost: Free
Info: This local festival is back for another year. Shop from over 90 local businesses at the Brighton Bazaar pop-up, enjoy yummy bites from local restaurants, and enjoy live music by local indie bands at this weekend party.
When: Sat. 10/18
Where: Revere
Cost: $0+
Info: You don’t need to run the Pumpkin Dash to enjoy the festivities. Cheer on participants and stay for the post-race party. There will be live music, a beer garden, giant pumpkin carving demos, and other fall-themed activities for all ages.
80) The Huntington Presents: Boston Women’s Market
When: Sat. 10/18
Where: South End
Cost: Free
Info: Local women-owned brands will be taking on the iconic stage of the Huntington Theatre. Celebrate community, creativity, and local talent, and shop for handmade goodies from over 20 small businesses.
81) Autumnal Grown Up Book Fair at Aeronaut Brewing
When: Sat. 10/18
Where: Somerville
Cost: Free
Info: Grab a brew and shop for your next cozy read at this grown-up book fair. There will be fun trinkets like stickers, socks, and mood rings (flashback to those middle school Scholastic days) too. Bring your friends and enjoy some bookish fun.
When: Sat. 10/18 - Sun. 10/19
Where: Roslindale
Cost: Free
Info: Don’t miss Roslindale’s largest celebration of art. Throughout the weekend, you can explore over 40 locations from home studios and local businesses to other group sites where you can connect with local artists. There will be live music, bingo, art demos, and more.
When: Sat. 10/18 - Sun. 10/19
Where: Newton
Cost: Free
Info: Celebrate fall with a carnival and outdoor festival at Newton Centre. Enjoy live music, games, international food trucks, and fair rides. You can take home a complimentary pumpkin, shop from local artists and vendors, and so much more.
When: Sat. 10/18 - Sun. 10/19
Where: Roslindale
Cost: Free
Info: Learn about plant-based food and products at the annual Boston Veg Fest. Learn from speakers and chefs, explore educational exhibits, taste some yummy plant-based samples, and grab some new items for your pantry.
85) SomerStreets: Monster Mash
When: Sun. 10/19
Where: Somerville
Cost: Free
Info: Spend your afternoon in spooky Somerville at this Halloween celebration. Wear your best costume, cheer on the parade, listen to live music, shop from craft vendors, and eat some yummy food too. Enjoy fun activities for all ages at this spooktacular block party.
86) Atlantic Wharf’s Fall Fest
When: Sun. 10/19
Where: Rose Kennedy Greenway
Cost: Free
Info: Celebrate fall with the Boston community right along the water at Atlantic Wharf. There will be live music, magic shows, an instrument petting zoo, and other fun activities for people of all ages. Munch on some cider donuts while enjoying harborfront views too.
When: Sun. 10/19
Where: Somerville
Cost: Free
Info: The Arts at the Armory is hosting an epic art market full of creative goodies. Meet artists, shop for handmade and vintage gifts, and celebrate art at this pop-up featuring over 30 local creatives.
When: Sun. 10/19
Where: Somerville
Cost: Free
Info: Make your way to Assembly Row for an afternoon of music and art. Shop from local artisans and vendors right along the Mystic River, listen to live music, and spend a fall day outdoors at this community event.
When: Sun. 10/19
Where: Seaport
Cost: Free
Info: Support Black-owned businesses from across the Greater Boston area at this monthly pop-up that elevates Black entrepreneurs and artists. Shop for art, food, beauty & skincare products, and other fun items.
When: Sun. 10/19
Where: City Hall Plaza
Cost: Free
Info: Head to City Hall Plaza for this Indigenous cultural event. There will be live music, dance performances, and a concert that pays tribute to local Black history. Learn about Native American history and the Indigenous land that Boston resides on, and observe a cleansing ritual of City Hall.
91) Thrift (S)hop
When: Sun. 10/19
Where: Jamaica Plain
Cost: Free
Info: Grab a refreshing drink at the Sam Adams Brewery and enjoy some weekly live music. As you relax before the work week begins, you can shop for local goodies at this monthly pop-up that features 3-5 vendors.
92) Beer Garden Pop UPs with Lamplighter
When: Thu. 10/23
Where: Kendall Square
Cost: $0+
Info: Don’t miss the final Lamplighter Brewing pop-up at the Urban Park rooftop garden for the 2025 season. Make a $5 donation for a beer token and enjoy your brew at this colorful urban oasis. Cheers!
When: Thu. 10/23
Where: Fenway
Cost: $5
Info: Enjoy special admission pricing to the MFA after 5PM and come celebrate Diwali. At this festival of lights, you’ll get to spend time with family and friends while exploring art, watching cultural performances, and more.
94) Twilight at MAAM: Noodle & Doodle with Doctor Gasp
When: Thu. 10/23
Where: Fenway
Cost: Free
Info: MassArt Art Museum is hosting another after-hours museum party with a Halloween twist. Sip on a complimentary mocktail, explore the galleries, and listen to live music while doodling and making some art.
95) Stitch and Screen: ‘Pride & Prejudice’ Craft Night
When: Thu. 10/23
Where: Kendall Square
Cost: Free
Info: Nothing screams cozy like a movie night in with crafts and friends. Head to MIT Welcome Center for a screening of ‘Pride & Prejudice’ and bring your current work in progress or crafting activity.
96) Halloween Trivia
When: Fri. 10/24
Where: Downtown
Cost: Free
Info: Boston Public Market is hosting a festive trivia night full of spooky fun and prizes. Grab a snack and a treat from one of the vendors, and then get ready to show off your trivia knowledge.
When: Sat. 10/25
Where: Back Bay
Cost: Free
Info: Copley will once again be bustling with literary festivities for the annual Boston Book Festival. Enjoy author talks, bookish giveaways, writing activities and activations, and so much more. Connect with other book lovers and celebrate the power of storytelling at this can’t-miss Boston event.
98) 4th Annual Seasonal Salvage Sale & Makers’ Market
When: Sat. 10/25
Where: Somerville
Cost: Free
Info: Head to the Somerville Community Growing Center for a huge secondhand sale. Shop for curated, seasonal items during the Salvage Sale and support local businesses and artists during the makers’ market.
99) Halloween Block Party and Pet Spooktacular
When: Sat. 10/25
Where: Somerville
Cost: Free
Info: Get ready for a Halloween block party featuring cute furry friends dressed in even cuter costumes. There will be live music, food and art vendors, activities for all ages, and so much more.
When: Sat. 10/25
Where: Downtown Crossing
Cost: Free
Info: Celebrate Halloween early with friends and family. Cheer on the Halloween Pet Parade featuring furry friends in the cutest costumes. Enjoy free samples of clam chowder, a vendor village, games, and other fun activations.
101) Rock the Plaza
When: Sun. 10/26
Where: City Hall Plaza
Cost: Free
Info: Head to City Hall Plaza for a beer garden and some live music, so you can show off your dance moves. Join this celebration that features a lineup of performances that highlight senior women in rock music. Bring your kiddos too since there will be children-friendly songs.
102) Pumpkin Stroll at Boston Public Market
When: Sun. 10/26
Where: Downtown
Cost: Free
Info: Go on a scavenger hunt for colorful pumpkins along the Greenway and then head to Boston Public Market for a Halloween bash. Make some crafts, decorate cookies, take photos by the giant (and we truly mean giant) pumpkins.
103) Tall Ship Boo Bash
When: Sun. 10/26
Where: Eastie
Cost: Free
Info: Bring your friends and family to one of the most iconic floating bars in the city — Tall Ship. Breathe in crisp autumn air with skyline views while enjoying a family-friendly Halloween party featuring characters, food specials, games, and more.
104) Boston Hassle Flea
When: Sun. 10/26
Where: Cambridge
Cost: $2
Info: Check out this flea and art market at the Cambridge Community Center featuring over 85 small businesses. There will be live music, art friends, a cafe, and fun goodies for purchase.
105) PruBoo
When: Sun. 10/26
Where: Back Bay
Cost: Free
Info: Enjoy the 31st Annual PruBoo at the Prudential Center. Come dressed in your favorite costume, make some Halloween crafts, enjoy magic shows and musical performances, and so much more.
106) The Night BOOzaar
When: Thu. 10/30
Where: Brighton
Cost: Free
Info: The Brighton Bazaar is bringing back their spooky outdoor market: The Night BOOzaar. Check out the activation room, grab some free Culture Pop, sip on brews while you shop from over 100 small businesses selling spooky items, and grab something to eat from the vendors and food trucks on-site.
107) Moon Over Bow
When: Thu. 10/30
Where: Union Square
Cost: Free
Info: Bow Market is hosting the witchiest night in the city. Enjoy themed food and drink specials around the courtyard, grab a tarot reading, and shop for some spooky, mystical goodies from local vendors. There will be fun activities like candle making and a spellwork station too.
108) Harvard Art Museums at Night
When: Thu. 10/30
Where: Harvard Square
Cost: Free
Info: Your favorite after-hours museum party is back to close out the month. Head to Harvard Art Museums and explore over 50 galleries. Make some art, take a spotlight tour, enjoy the tunes of a DJ in the courtyard, and enjoy food and drink pop-ups too.
109) BLAIR 2025
When: Fri. 10/31
Where: City Hall Plaza
Cost: Free
Info: Prepare yourself for the ultimate Halloween takeover at City Hall Plaza. Celebrate culture, community, and chaos at this evening party featuring a food truck village, live music (with an all-women line-up of DJs), a vendor market, and so much more.
110) Halloween Party at Castle Island
When: Fri. 10/31
Where: Southie
Cost: Free
Info: Happy Halloween — come dressed in your best costume and head to Castle Island for spooky fun. Cheers with great brews, even greater DJ tunes, and the greatest vibes at this bash.
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SponsoredBoston Harborfest 2026: Celebrating America’s 250th
Thursday, Jul 02, 2026 goes until 07/04
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