102 Things to Do in Boston for $10 or Less: May 2025
When:
Thursday, May 01, 2025 7:00a -
Saturday, May 31, 2025 11:00p
Thursday, May 01, 2025 7:00a -
Saturday, May 31, 2025 11:00p
Where:
Greater Boston Area
Greater Boston Area
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, Seasonal, Shopping, Sports & Active Life
May is here, my Boston friends. Indulge in the warm weather and soak up the beaming sun rays as you enjoy the return of outdoor markets, dance parties, cultural festivals, and so much more. Here are the best free and cheap things to do around the city this May.
by Yelena Nicolle Salvador
1) Boston May Day Rally & March
When: Thursday 5/1
Where: Boston Common
Cost: Free
Info: Stand up and make your voice heard by joining the May Day rally. Show your solidarity and support for fair housing, healthcare, wages, and more.
2) ‘Perks of Being a Wallflower’ Screening
When: Thursday 5/1
Where: Back Bay
Cost: Free
Info: Kick off Mental Health Awareness Month by catching a screening of ‘Perks of Being a Wallflower.’ Grab a bite to eat at the cafe upstairs, get cozy, and grab a box of tissues while watching this flick.
When: Thursday 5/1 - Saturday 5/3
Where: Jamaica Plain
Cost: Free
Info: Celebrate the mighty tree during ArborWeek. Enjoy free programming like guided walks, tree giveaways, and the grand festival finale: the Wake Up the Earth Festival featuring live music, dancing, food trucks, and craft vendors.
When: Thursday 5/1 - Sunday 5/4
Where: Harvard Square
Cost: Free
Info: Enjoy art all weekend long and feel inspired. At the Harvard Arts Festival, you can celebrate the creativity of the Harvard arts community through shows, performances, art-making activities, and exhibitions.
5) Downtown Boston Arts Market
When: Thursdays and Fridays, starting 5/1
Where: Downtown
Cost: Free
Info: Downtown will be bursting with life and art with the return of the Downtown Boston Arts Market. Shop small and local and discover the talented folks within our city who are making and curating the perfect gifts.
When: Daily except Sundays, starting 5/1
Where: Seaport
Cost: Free
Info: One of the biggest free outdoor fitness series is back. Enjoy community classes with experienced instructors and break a sweat whether you are enjoying yoga and pilates or HIIT and Zumba.
7) National Bike Month with Bluebikes
When: Daily, starting 5/1
Where: Boston
Cost: Free
Info: Happy National Bike Month. Enjoy a free $50 credit for Bluebikes and explore the city all month long while making the Earth a little greener.
8) SoWa First Friday & Art Walk
When: Friday 5/2
Where: South End
Cost: Free
Info: Kick off the first weekend of May at SoWa. Enjoy an evening of art where you can explore several art galleries, meet with artists and see them create, and mingle with other art lovers.
9) Artwear: The SOS 2025 Fashion Show
When: Friday 5/2
Where: Davis Square
Cost: Free
Info: Get ready for a beautiful fashion show at the Crystal Ballroom. At Artwear, you can see clothing and wearable fine art, enjoy a cocktail hour, and feel inspired by innovative fashion designers and creators.
10) Club Volo Spring Kick-Off Party
When: Friday 5/2
Where: Somerville
Cost: Free
Info: Welcome spring with Club Volo and new friends. Play some volleyball, pickleball, bocce, and other outdoor games while sipping on some fun drinks and meeting folks in the community.
11) Grrrl Talk at Remnant Satellite
When: Friday 5/2
Where: Cambridge
Cost: Free
Info: This party is for the ladies, by the ladies. Get ready for an evening of vinyl faves, dancing, drinking, and mingling with ladies, new friends, and lovers.
When: Friday 5/2
Where: Seaport
Cost: Free
Info: The new season of the Seaport Current is here. Come celebrate the local businesses that will be taking up shack for the next few months with this opening party featuring free giveaways, live music, a s’mores cart, and more.
13) Roundhead Cerveza Que Reúne Beer Garden
When: Fridays & Saturdays, starting 5/2
Where: Jamaica Plain
Cost: Free
Info: Roundhead Brewing is hosting a pop-up beer garden all over the city for the next few months. This month’s stop is Jamaica Plain. Sip on great beer, enjoy the outdoors, listen to live music, and more.
When: Saturday 5/3
Where: Public Garden
Cost: Free
Info: Soak up the sunshine and meet new friends at this 20s and 30s picnic social in collaboration with Boston Babes Social. Bring your favorite food and shareable snacks and get ready to mix and mingle.
15) North Cambridge Spring Stroll
When: Saturday 5/3
Where: North Cambridge
Cost: Free
Info: Say hello to spring and explore North Cambridge by foot. On this spring stroll, you can taste some food and grab a recipe card from participating shops and restaurants. You can also participate in a scavenger hunt, explore the small businesses in the area, and more.
16) Lucky 7’s: Anniversary Party
When: Saturday 5/3
Where: Somerville
Cost: Free
Info: Remnant Brewing is turning seven years old. Come join the party where you can enjoy the patio, sip on a new release IPA, and munch on some sheet cake. Get ready for even more fun – cheers to many more years!
17) German International School Flohmarkt
When: Saturday 5/3
Where: Allston
Cost: Free
Info: The German International School of Boston is hosting their annual flea market. Shop for new treasures, meet others in the community, enjoy the outdoors, and more.
18) Short Path Free Distillery Tour
When: Saturday 5/3
Where: Everett
Cost: Free
Info: Enjoy a free tour of Short Path Distillery where you can get up close to the stills, barrelhouse, and brewhouse. Learn about the entire process of making bevs and sample three spirits too.
When: Saturday 5/3
Where: Central Square
Cost: Free
Info: It’s block party season. Enjoy an outdoor party in Central Square featuring local bites, live music, family-friendly activities, and other interactive experiences for everyone to have fun.
20) Love Your Block in Fort Point
When: Saturday 5/3
Where: Fort Point
Cost: Free
Info: Help keep Fort Point clean by participating in a community cleanup since every day should be treated like Earth Day. Connect with neighbors and local organizations, enjoy the outdoors, and support the neighborhood.
21) Derby Day at Time Out Market
When: Saturday 5/3
Where: Fenway
Cost: Free
Info: Watch the Kentucky Derby in style. Head to Time Out for themed cocktails, a live DJ, a hat competition with fun prizes, and an epic watch party with race day vibes all day long.
When: Saturday 5/3
Where: Everett
Cost: Free
Info: It’s Derby weekend and race day isn’t just reserved for horses. Head to Park-9, grab a beer, and watch the ultimate showdown of corgis and dachshunds as they compete for the Park-9 Derby crown.
23) Somerville Open Studios 2025
When: Saturday 5/3 - Sunday 5/4
Where: Somerville
Cost: Free
Info: Explore Somerville by foot and celebrate the talented artists in the neighborhood. For two days, you can visit over 100 locations in houses, galleries, and studio spaces, meet over 400 artists, and enjoy beautiful exhibits across town.
When: Saturdays, starting 5/3
Where: Rose Kennedy Greenway
Cost: Free
Info: This outdoor market that lines the Greenway on the weekend is back for the season. Shop small and local from over 50 vendors, soak up the rays of sunshine, and enjoy the breeze and views of the waterfront.
When: Saturdays, starting 5/3
Where: Boston Common
Cost: Free
Info: Outdoor market season has returned. Discover the talent of artisans from across New England while taking in the views of the Common on the weekends at this art market.
26) 40th Annual Mayfair in Harvard Square
When: Sunday 5/4
Where: Harvard Square
Cost: Free
Info: One of the biggest spring festivals in Boston is back for its 40th year. Head to Harvard Square for a day full of multicultural celebration. Enjoy live performances, beer gardens, art installations and vendors. Don’t miss this the 3rd Annual Asian Street Food and Music Festival for even more fun.
27) Book Wars: Sci-Fi & Fantasy Bookfair
When: Sunday 5/4
Where: Back Bay
Cost: Free
Info: May the Fourth be with you my fellow Star Wars lovers. Head to Trident for a themed book fair featuring fantasy and sci-fi reads, droid building, tarot and star chart readings, fun cocktails, and more.
28) Cinco de Mayo at Bow Market
When: Sunday 5/4
Where: Somerville
Cost: Free
Info: Celebrate Cinco de Mayo early at Bow. A live DJ will be spinning tunes as you enjoy the courtyard; grab a taco, churro, or tamale; shop from local vendors; and relax with a marg.
29) Star Wars Movie Marathon at Lamplighter CX
When: Sunday 5/4
Where: Cambridge
Cost: Free
Info: In true May 4th fashion, you can enjoy a Star Wars movie marathon while sipping on some beer. Don your Jedi robes (or Sith cloaks) and get ready to party it up with the force all day long as you watch the entire Star Wars saga.
30) Legal Sea Foods Rooftop Cinco de Mayo Party
When: Sunday 5/4
Where: Seaport
Cost: Free
Info: Legal Sea Foods is hosting a rooftop party to celebrate Cinco de Mayo. Soak up the sunshine while taking in waterfront views, dance to the tunes of a DJ, munch on $2 oysters, and more.
31) SoWa Open Market
When: Sundays, starting 5/4
Where: South End
Cost: Free
Info: The beloved SoWa Open Market is back for the season. Stroll through the galleries, shop from local vendors, grab a bite from a food truck, and enjoy the return of outdoor market season.
When: Monday 5/5
Where: Downtown
Cost: Free
Info: Celebrate Cinco de Mayo with live Mexican folk music, great food, a vendor market, and more. Join friends from Boston’s Consulate General of Mexico in Downtown for this cultural party for all.
When: Wednesday 5/7
Where: South End
Cost: Free
Info: The annual South End Spring Stroll is back where you can shop from local establishments, enjoy patio season at a local restaurant, and savor a beautiful spring evening in the neighborhood.
34) Mother’s Day Market at Atlantic Wharf
When: Wednesday 5/7
Where: Atlantic Wharf
Cost: Free
Info: Find the perfect gift for mom, your bestie, your aunt, your grandma, or yourself, at the Mother’s Day Market at Atlantic Wharf. You can find handmade jewelry, candles, and other gifts from local women-owned businesses.
35) Astronomy on Tap Boston: The Dark Side of the Force
When: Wednesday 5/7
Where: Somerville
Cost: Free
Info: Head to Aeronaut Brewing for a fun talk that is perfectly themed with May the Fourth and Star Wars. Join Harvard Professor Cora Dvorkin while you grab a brew and learn more about dark energy and the evolution of the universe.
36) Grand Ten Line Dancin’ Lessons
When: Wednesdays 5/7 & 5/21
Where: Southie
Cost: Free
Info: Honky Tonk Way through a fun night at Grand Ten where you can enjoy three hours of nonstop line dancing and lessons. Learn how to two-step and get ready for a full night of country lovin’ tunes and energy.
37) South Boston Spring Stroll
When: Thursday 5/8
Where: Southie
Cost: Free
Info: Explore Southie by foot and enjoy an evening spring stroll through the neighborhood. Enjoy restaurant specials and discounts at local stores, listen to live music, and hop on a free pedicab ride while connecting with other community members.
38) Birding 101
When: Thursday 5/8
Where: Kendall Square
Cost: Free
Info: Get your birding on and don’t forget your binoculars to spot some local wildlife. Take a short stroll, enjoy a guided walk, and learn how to listen for and spot some birds.
When: Friday 5/9
Where: Harvard Square
Cost: Free
Info: Meet new friends while hunting for the best ice cream spot in Cambridge. Grab a scoop from Lizzy’s, Christina’s, and Gracie’s and then mix and mingle at Aeronaut.
40) Free Outdoor Meditation at the Boston Public Garden
When: Friday 5/9
Where: Public Garden
Cost: Free
Info: Relax after a long week with a free guided outdoor meditation at the Public Garden. Learn how to practice mindfulness and meet some neighbors as you kick off your weekend with a rejuvenating session.
41) Last Boss Beer Release Party
When: Friday 5/9
Where: Downtown
Cost: Free
Info: Sam Adams is releasing an exciting new beer: a blueberry blackberry sour called the Last Boss. To kick off this celebration, you can try out this new brew while playing board games, hopping on a retro game machine, and shopping from local vendors.
42) Retro Video Game Night at Castle Island
When: Friday 5/9
Where: Southie
Cost: Free
Info: Battle it out with new friends at this 21+ only adult game night. Play your favorite games from Mario Kart to Street Fighter while sipping on some brews at Castle Island in Southie.
43) GyroFest
When: Friday 5/9 - Saturday 5/10
Where: Somerville
Cost: Free
Info: Learn about Greek culture and enjoy Greek cuisine all weekend long. Munch on gyros, spanakopita, and baklava while sipping on some beer or wine. Bring a blanket and enjoy the food picnic style before you head out to PorchFest too.
44) Mother’s Day Market at Boston Public Market
When: Friday 5/9 - Sunday 5/11
Where: Downtown
Cost: Free
Info: Shop for the perfect handmade gift for yourself or a loved one at Boston Public Market. Grab something to munch on and sip on a fun bev while you peruse the stalls who will be selling jewelry, food, pottery, candles, and more.
When: Saturday 5/10
Where: Somerville
Cost: Free
Info: It’s time for one of the most iconic events in the Greater Boston area: PorchFest. Celebrate the talent of local musicians as they perform a variety of musical genres on porches, driveways, lawns, and more. Get ready to walk, dance, and sing along at this beloved community event.
46) Revere Beach Kite Festival
When: Saturday 5/10
Where: Revere
Cost: Free
Info: Warmer weather means beach season is here. Head to Revere for their annual Kite Festival where you can build, decorate, and fly your kites right along the water. There will be live music, professional kite flyers, and other family-friendly activities.
47) Be-In Joy Boston
When: Saturday 5/10
Where: Boston Common
Cost: Free
Info: Now more than ever, we need to focus on recentering joy. Join this festival on the Common where you can connect with new friends with conversational prompts, learn how to dance, and enjoy other fun community activities.
When: Saturday 5/10
Where: Roslindale
Cost: Free
Info: Come with an empty stomach and get ready to eat a lot of good food at this mini Greek food festival that celebrates the gyro. Pair it with crunchy fries and top it off with a sweet treat of loukoumades.
49) Wicked Local Wares Pride Market
When: Saturday 5/10
Where: Fenway
Cost: Free
Info: Head to Time Out Market and grab a bite to eat or a fun drink while supporting local LGBTQIA+ businesses. Sip and shop for your next gift for yourself or someone you love.
50) Boston Women’s Market at Assembly Row
When: Saturday 5/10
Where: Roslindale
Cost: Free
Info: Boston Women’s Market is hosting a pop-up featuring over 30 local women-owned businesses at Assembly Row. Enjoy a snack and shop for unique handmade gifts and goods at this outdoor market.
51) Small Mart Market at Crystal Ballroom
When: Saturday 5/10
Where: Davis Square
Cost: Free
Info: Small Mart is hosting one of their big vintage, handmade, and artisan markets at Crystal Ballroom. Shop from over 40 local businesses, sip while you peruse, and connect with other community members.
52) The JOY Party
When: Saturday 5/10
Where: Cambridge
Cost: Free
Info: Kick off outdoor dance party season with the JOY Party. Boston-based DJs will be serving up tunes across all genres for everyone to enjoy. Bring your friends and family and celebrate this multicultural and intergenerational community gathering.
53) Bloom Studio Group Launch Party
When: Saturday 5/10
Where: Somerville
Cost: Free
Info: Welcome this business to the Somerville scene and enjoy an art and vintage market, live music, and a film screening. Meet other artists and art lovers and learn more about Bloom Studio Group, a New England-based production company.
54) Boston Chamber Symphony Historic Free Concert
When: Saturday 5/10
Where: Newton
Cost: Free
Info: Enjoy an evening of classical music with the Boston Chamber Symphony. Listen to the soothing tunes of the cello, piano, and other instruments at this community concert.
55) 21st Annual Union Square Farmers Market
When: Saturdays, starting 5/10
Where: Union Square
Cost: Free
Info: The Union Square Farmers Market is back for its 21st season. Shop from over 60 local food producers who will be selling fruit, veggies, jam, bread, hot sauce, and so much more.
56) Seaport Summer Market 2025
When: Saturdays & Sundays, starting 5/10
Where: Seaport
Cost: Free
Info: Get ready for outdoor market season in Seaport. Enjoy shopping from local vendors, listen to the tunes of a DJ, play some lawn games, and grab a bite to eat from the food trucks on site. Bring your pups to join the fun too.
57) Lilac Sunday at the Arnold Arboretum
When: Sunday 5/11
Where: Jamaica Plain
Cost: Free
Info: You don’t want to miss this favorite annual spring event at the Arnold Arboretum. Stroll through the gardens that will be blooming with beautiful hues of blue and purple lilacs. Enjoy a picnic, listen to live music, watch dance performances, and participate in guided meditations.
58) Duckling Day
When: Sunday 5/11
Where: Boston Common
Cost: $0+
Info: Cheer on the cute-dressed duckies that will be waddling their way through the Common during the Duckling Day Parade and celebrate the story behind the beloved ‘Make Way for Ducklings’ sculpture.
When: Sunday 5/11
Where: Assembly Row
Cost: Free
Info: Meet new friends and join this casual stroll where you can chat with others who are looking to grow their community. Enjoy the outdoors and soak up the sunshine with great company.
When: Thursday 5/15
Where: Downtown
Cost: Free
Info: Get ready for beach season with your next perfect beach read. While sipping on a brew from Sam Adams, shop from a curated selection of the best summer romances and stories with friends from Trident.
61) Ruby Grove with the Velvet Dirtymunchers Concert
When: Thursday 5/15
Where: Brighton
Cost: Free
Info: Enjoy a free live concert at Notch Brewery featuring Ruby Grove, a New England music award-nominated indie rock band. Don’t miss the tunes of the funk and soul group, Velvet Dirtymunchers. Grab a brew and a bite and get ready to dance.
62) Boston’s National Bike to Work Day Festival
When: Friday 5/16
Where: City Hall Plaza
Cost: Free
Info: Happy National Bike to Work Day Festival. Get on your bike and get ready to pedal all the way to City Hall Plaza. Enjoy an afterparty featuring coffee, donuts, and community connection.
63) Aeronaut Allston Opening Weekend
When: Friday 5/16 - Saturday 5/17
Where: Allston
Cost: Free entry; Pay as you go
Info: It’s the final year of Aeronaut’s pop-up in Allston Zone 3. Don’t miss opening weekend and the final weeks of this beer garden featuring live bands, food trucks, markets, lawn games, and more.
64) Block Party & Vintage Market at Harvard Square
When: Saturday 5/17
Where: Harvard Square
Cost: Free
Info: Select Markets is hosting a massive block party and thrift market featuring over 100 vendors. Enjoy live music, grab a free drink, shop for some hidden treasures, and get ready to party in Harvard Square.
65) Franklin Park Kite & Bike Festival
When: Saturday 5/17
Where: Roxbury
Cost: Free
Info: Spring is here at Franklin Park. Join the 50-year tradition of the Kite & Bike Festival where you can enjoy the open park; make, buy, bring, and fly a kite; and grab a bite to eat at a food truck.
When: Saturday 5/17
Where: Somerville
Cost: Free
Info: Celebrate Haitian culture and the local Haitian community at the Haitian Flag Festival. Enjoy live music, taste some traditional Haitian dishes, and learn about Haitian culture at this neighborhood get together.
When: Saturday 5/17
Where: Watertown
Cost: Free
Info: Listen to live music all across the neighborhood of Watertown. Celebrate the talent of local musicians as they play tunes in driveways, patios, porches, and more. Don’t forget to explore businesses around town who will be continuing the musical fun.
68) Community Boating, Inc. Open House
When: Saturday 5/17
Where: Charles River Esplanade
Cost: Free
Info: Community Boating, Inc. on the Esplanade is hosting an open house. Play lawn games, decorate a sail, learn about the history of the company and the boathouse, and enjoy a free sail on the Charles.
When: Saturday 5/17
Where: Rowes Wharf
Cost: Free
Info: The beloved Greenway Food Truck Festival is returning this year with a new name: Spring Fest. Get ready to munch on eats from 15 food trucks; try your hand at a Greenway fitness class; take a ride on the carousel; and more.
70) Boston Women’s Market at Downtown Crossing
When: Saturday 5/17
Where: Downtown
Cost: Free
Info: Head to Downtown Crossing and celebrate the return of outdoor market season. Shop from 20 local women-owned businesses – each vendor will be highlighting their current favorite product at this special edition of Boston Women’s Market.
71) Quincy Multicultural Festival
When: Saturday 5/17
Where: Quincy
Cost: Free
Info: Celebrate the diverse community of Quincy at the Multicultural Festival. There will be live music and cultural displays from around the world, food vendors that represent a wide variety of global cuisine, and other family-friendly activities for everyone.
72) Restoration of Memorial Hall Open House
When: Saturday 5/17
Where: Charlestown
Cost: Free
Info: Charlestown’s Historic Memorial Hall is reopening to the public after 10 years of dedicated restoration. Enjoy this open house, meet community members, and learn about the history of this building and the neighborhood.
73) The Greater Roxbury Book Fair
When: Saturday 5/17
Where: Roxbury
Cost: Free
Info: The annual Greater Roxbury Book Fair is back for its third year. Meet local writers and other book lovers while shopping for your next read and learning from local and BIPOC authors during engaging talks.
74) Spring Fling
When: Saturday 5/17
Where: Seaport
Cost: Free
Info: Get a sneak peak of a Seaport summer at the Spring Fling picnic. Listen to a live DJ, enjoy complimentary bites from local establishments, grab a beer, and so much more.
When: Saturday 5/17
Where: Seaport
Cost: Free
Info: Volunteer and help plant flags that each honor a Massachusetts Fallen Hero. Connect with the community and celebrate the service of those in the Armed Forces.
When: Saturday 5/17 - Sunday 5/18
Where: Long Wharf
Cost: Free
Info: Kick off ferry season with a free ride to Spectacle Island, one of the Boston Harbor Islands. Bring a picnic and get ready to stroll along the beaches and trails of this beautiful place after enjoying the breeze of the harbor on a boat.
When: Sunday 5/18
Where: Dorchester
Cost: Free
Info: Learn about Polish culture and celebrate Boston’s Polish-American community at this festival. There will be great food, live music performances, cultural demonstrations, and other family-friendly activities for everyone to enjoy.
When: Sunday 5/18
Where: Inman Square
Cost: Free
Info: Celebrate the neighborhood of Inman Square and its local businesses. Stroll through the car-free streets, munch on good eats, learn about the neighborhood, and shop from local vendors.
When: Sunday 5/18
Where: Seaport
Cost: Free
Info: Shop small and local, especially from Black-owned businesses in this area. Find specialty and artisanal goods from art and jewelry to food and other goodies.
80) Swiftie Sunday
When: Sunday 5/18
Where: Fenway
Cost: Free
Info: Party it up with your favorite Swiftie era. Don’t forget your glitter, your red lipstick, and your friendship bracelets while you dance it out to your favorite Taylor tunes and sip on Tay-themed drinks.
81) Thrift (S)hop
When: Sunday 5/18
Where: Jamaica Plain
Cost: Free
Info: Head to Sam Adams Brewery to find your next treasure. Grab a brew, sip on it on the patio, listen to live music, and shop from 3-5 local vendors for your next perfect gift for yourself or a loved one.
82) 2025 Watertown Dam Herring Festival
When: Sunday 5/18
Where: Watertown
Cost: Free
Info: It’s time for the annual migration of Alewife, Blueback Herring, and American Shad from the ocean to the Charles River. Enjoy community connection, birding, food trucks, art, and more at this festival.
83) 2025 Fitness on the Greenway
When: Daily except Fridays, starting 5/19
Where: Rose Kennedy Greenway
Cost: Free
Info: Get outside and enjoy free fitness classes with the return of the Fitness on the Greenway series. Break a sweat with HIIT, learn the basics of parkour and tai chi, relax with some yoga and pilates, and so much more.
84) Sam Sessions Mini Music Festival
When: Thursday 5/22
Where: Jamaica Plain
Cost: Free
Info: Celebrate the Boston Calling Music Festival early by enjoying a mini live music festival at Sam Adams. Grab a brew and enjoy the tunes of six local artists who will be jamming out on two different stages at this beer garden.
85) ‘Mean Girls’ Outdoor Movie at Boston Landing
When: Thursday 5/22
Where: Brighton
Cost: Free
Info: Outdoor movie season is back at Boston Landing. Watch ‘Mean Girls’ on the big screen and enjoy live music, snacks and bevs, and an iconic film under the stars.
86) Massachusetts Fallen Heroes: Memorial Day Fireworks
When: Saturday 5/24
Where: Seaport
Cost: Free
Info: Celebrate Memorial Day and the fallen heroes who gave up their lives with a commemorative fireworks display along the waterfront. Get there early to enjoy live music, interactive experiences, and other family-friendly activities before watching the show.
87) Courtroom Kiki! Drag Brunch & Bingo
When: Saturday 5/24
Where: Fenway
Cost: Free
Info: Kick off your weekend with a fun drag show and the ultimate bingo bash with prizes. Get ready for sketch comedy, drag queens who will be serving the stage, themed cocktails, and more.
88) Memorial Day Weekend Bazaar
When: Saturday 5/24 - Sunday 5/25
Where: Brighton
Cost: Free
Info: The Brighton Bazaar is hosting a two-day market event at the Speedway. Sip on a brew from Notch, shop from over 100 local businesses, grab a bite from a food truck or stall, and enjoy the outdoor fun.
89) Time Out’s Best Margarita in Fenway Competition
When: Sunday 5/25
Where: Fenway
Cost: Free
Info: Get ready to vote for the best marg in town. Head to Time Our Market and sip on free samples of margaritas from different Fenway establishments and see who comes out on top.
90) Free MFA Admission on Memorial Day
When: Monday 5/26
Where: Fenway
Cost: Free
Info: Enjoy free admission to the MFA this Memorial Day. There will be spoken word performances, live music, art making, and access to the special ‘Van Gogh: The Roulin Family Portraits’ exhibit.
91) Free ICA Admission on Memorial Day
When: Monday 5/26
Where: Seaport
Cost: Free
Info: The ICA is offering free admission this Memorial Day. Explore beautiful galleries of contemporary art while taking in expansive waterfront views. Grab a drink or a snack and enjoy some light bites from the wine bar onsite too.
92) Boston Conversations - May Event
When: Monday 5/26
Where: Somerville
Cost: Free
Info: Meet new friends at this event where you can skip the surface level chit chat and get into the nitty gritty. Enjoy chosen prompts that will allow you to get to know strangers on a deeper level and grow your community.
When: Tuesday 5/27
Where: City Hall Plaza
Cost: Free
Info: Celebrate Guyana independence and learn about the Guyanese-Bostonian community by joining leaders and the members of the Guyanese diaspora during this flag-raising and cultural ceremony.
94) Harvard Art Museums at Night
When: Thursday 5/29
Where: Harvard Square
Cost: Free
Info: This community favorite after-hours museum party is back. Explore 50+ galleries, dance to the tunes of DJ C-Zone in the Italian-inspired courtyard, munch on some fun bites, and sip on fun bevs while making some art and feeling inspired.
When: Thursday 5/29
Where: Fenway
Cost: Free
Info: Hips don’t lie at Time Out Market. Get ready for a live DJ spinning your favorite Shakira tunes, Shakira-inspired drink specials, and other fun at this pregame party before the queen hits the stage on the Fenway field.
96) Jason Aldean and Brooks & Dunn Pregame Party
When: Friday 5/30
Where: Fenway
Cost: Free
Info: Get your country on at Time Out Market. Whether you are catching the Jason Aldean and Brooks & Dunn concert at Fenway or just want to enjoy the country vibes, party it up, sip on themed cocktails, and listen to DJ beats.
97) New England Hong Kong Festival
When: Saturday 5/31
Where: Somerville
Cost: Free
Info: It’s time for the second annual New England Hong Kong Festival. Learn about Hong Kongese culture, munch on delicious bites, listen to live music, watch cultural performances, play some games, and enjoy other family-friendly interactive activities.
When: Saturday 5/31
Where: Southie
Cost: Free
Info: Southie is hosting their first ever Porchfest with their own twist: Stoopfest. Listen to live music on local neighborhood stoops, at restaurants and local businesses, and so much more. Welcome this new music festival to the community.
When: Saturday 5/31
Where: Allston
Cost: Free
Info: WBUR is hosting their first ever street fair in honor of their 75 years of journalism (and to many more). There will be live music, a mini Fluff festival, food trucks, a vintage market, and so much more.
100) Aeronaut’s 11th Anniversary
When: Saturday 5/31
Where: Somerville
Cost: Free
Info: A very happy birthday to the beloved Aeronaut Brewing. Get ready to party with aerialists and acrobatic performances, live music, games, blind taste testing, and so much more. Cheers to many more years.
101) Dorchfest 2025
When: Saturday 5/31
Where: Dorchester
Cost: Free
Info: Dorchfest is back for its third year. Get ready for all kinds of talented performances on porches, lawns, and driveways across the Greater Ashmont-Adams neighborhood and celebrate the community.
When: Saturday 5/31
Where: Malden
Cost: Free
Info: Listen to the tunes of local talent across the Malden neighborhood – porches, driveways, stoops, and more. Enjoy this music festival and listen to different genres with your neighbors.
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SponsoredGuided Tour of Historic Castle Hill on the Crane Estate: Round Trip Transportation from Boston Included!
Monday, May 26, 2025 11:30a
Crane Estate
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Sponsored -
SponsoredBoston Chocolate Tour - Beacon Hill to Boston Public Market
Saturday, May 24, 2025 11:00a
Meeting Spot
