When:
Friday, May 01, 2026 7:00a -
Sunday, May 31, 2026 11:30p

Where:
Greater Boston Area
Greater Boston Area
Boston, MA

EventScheduled OfflineEventAttendanceMode

Admission:
$0-10

Categories:
Art, Classes, Date Idea, Drinks, Festivals & Fairs, Food, Games, Good for Groups, History, Kid Friendly, LGBTQ+, Meetup, Movies, Music, Nature, Nightlife, Party, Photoworthy, Seasonal, Shopping, Social Good, Sports & Active Life

May is here, my Boston friends. Soak up the sun and the warmer weather now that we are one step closer to summer. Get outside with the return of peak blooms, beer gardens, patios, outdoor markets, dance parties, cultural and food festivals, and so much more.


by Yelena Nicolle Salvador


1) Spring Fling: May Day Celebration

When: Fri. 5/1

Where: Union Square

Cost: Free

Info: Head to Bow Market for a spring party! Enjoy a sidewalk sale as you stroll around the courtyard and the balcony for some bargain finds from your favorite stores. There will be a plant and clothing swap, themed beverages and food, and other fun surprises.


2) Picnic at The Current | Opening Day

When: Fri. 5/1

Where: Seaport

Cost: Free

Info: Your favorite tiny strip mall in the Seaport is reopening with a new theme: picnic! Come celebrate opening day with lawn games, a DJ, and some complimentary snacks like cotton candy and lemonade twists. There will also be special sales from the new stores. Experience a slice of summer at this party. 


3) Boston DSA’s May Day Field Day

When: Fri. 5/1

Where: North End

Cost: Free

Info: Celebrate International Labor Day at the North End Trellis. There will be live music, guest speakers, food and ice cream, and lawn games. Connect with neighbors and make some signs before the May Day Rally on the Common.


4) Boots for Bail

When: Fri. 5/1

Where: Copley Square

Cost: $9+

Info: Put your boots on and support a good cause by donating money to support the Mass Bail Fund. At this fundraiser, you’ll get to learn how to line dance — no experience necessary, while participating in a silent auction, shopping from local artists, and meeting new friends.


5) Little Songbook in Bloom

When: Fri. 5/1

Where: Somerville

Cost: Free

Info: Make your way to Somerville Community Growing Center for a one-year spring celebration featuring flowers and a concert. Enjoy live storytelling featuring works by Virginia Woolf and Amy Lowell, as well as opera and chamber music performances.


6) Harvard Arts Fest 2026

When: Fri. 5/1 - Sun. 5/3

Where: Harvard Square

Cost: Free

Info: Happy annual Harvard Arts Fest! Celebrate creativity at this all-ages festival where there will be over 100 performances. Participate in freestyle dance parties, a community mural, a choral sing-along, and more. There will also be crafting stations, exhibitions, and other fun activities. 


7) Black Business Spring Marketplace

When: Fri. 5/1 - Sun. 5/3

Where: Harvard Square

Cost: Free

Info: Support Black businesses during the Black Business Spring Marketplace Pop-Up. Sixteen local, Black-owned businesses will be offering fun items from soaps and sauces to jewelry, clothes, and skincare. 


8) MA250: The 250th Anniversary of Massachusetts

When: Ongoing, starting Fri. 5/1

Where: Boston & beyond

Cost: $0+

Info: Celebrate the 250th anniversary of America in the state that started it all. Keep your eye out for live reenactments, specialty tours, timely exhibits, and other fun surprises as you learn more about the history of our country.


9) East Boston Open Studios

When: Sat. 5/2

Where: East Boston

Cost: Free

Info: Head to Eastie for an Open Studios event where you can explore the work from over 25 local artists. Stroll around the Atlantic Works Artist Studio, The Gallery at Boston East, and Zumix where you can connect with other art-lovers and get up close and personal to distinct creative processes.


10) 20s & 30s Picnic Social

When: Sat. 5/2

Where: Boston Public Garden

Cost: Free

Info: Meet new friends at the Boston Public Garden. Bring foods and snacks you’d like to share, and get cozy on a blanket while you start conversations with neighbors. Connect with other 20- and 30-somethings at this get-together. 


11) 48th Annual Wake Up the Earth Festival

When: Sat. 5/2

Where: Jamaica Plain

Cost: Free

Info: Join neighbors from Roxbury and Jamaica Plain for the annual Wake Up the Earth Festival. There will be over 120 local vendors to support like artists and restaurants. There will also be four stages for live music and dance performances, as well as art-making stations and other fun activities.


12) Celebrate Cinco de Mayo at Bow Market

When: Sat. 5/2

Where: Union Square

Cost: Free

Info: Join Cinco de Mayo festivities at Bow Market. There will be Mexican food vendors and festive specials throughout the courtyard. Don’t miss the live music and fun atmosphere all afternoon.


13) 8-Year Birthday Party at Remnant Brewing 

When: Sat. 5/2

Where: Union Square

Cost: Free

Info: Happy 8th birthday to Remnant. Come celebrate by grabbing a brew or sipping on a special birthday cake cocktail. There will be cake, free sprinkles, and other fun birthday shenanigans. 


14) Gyro Festival

When: Sat. 5/2

Where: Roslindale

Cost: Free

Info: Munch on yummy Greek gyros, crispy fries, and delectable loukoumades at the St. Nectarios Greek Orthodox Church Gyro Festival. Come hungry and leave satisfied as you enjoy live music and shop from local vendors too.


15) Park-9 3rd Annual Dog Derby

When: Sat. 5/2

Where: Everett

Cost: Free

Info: It’s Derby Day! Come dressed to impress and head to Park-9 for some dog race fun. Cheer on the corgi, dachshund, and small dog competitions as you watch the Kentucky Derby on the big screen. There will be fun drinks and even better company.


16) Tony Williams’ Dorchester Dance Fest

When: Sat. 5/2

Where: Dorchester

Cost: Free

Info: Make your way to historic Strand Theatre for a one-day festival featuring ballet, modern, jazz, and other fusion dance style performances. Dancers of all ages and backgrounds will take the stage, so come celebrate the power of movement with others.


17) Earth Day Celebration

When: Sat. 5/2

Where: Charlestown

Cost: Free

Info: Stop by Charlestown’s Navy Yard for an Earth Day celebration. Bring your friends and family or come solo while you honor the Earth. There will be face painting, chalk art, seed planting, and shell fish petting too.


18) Nothing but Bangerz: Saxyderms 20th Anniversary Concert

When: Sat. 5/2

Where: Roslindale

Cost: Free

Info: The Saxyderms are celebrating their 20th anniversary. Check out their milestone concert which will be in Porchfest-style. Grab a mocktail or a fun bev, get cozy on the lawn, and take in the sounds of your favorite tunes from throughout the years.


19) Fiesta de Mayo

When: Sat. 5/2

Where: Fenway

Cost: Free

Info: Time Out Market is hosting a Cinco de Mayo celebration. Stop by for live music and a festive atmosphere as you celebrate Latin American heritage. There will be vendors, performances, and community organizations too.


20) German International School Flohmarkt

When: Sat. 5/2

Where: Allston

Cost: Free

Info: The German International School of Boston is hosting its annual flea market. As you soak up sunshine, grab a sweet treat from the bake sale, meet new friends, and shop for some treasures that support the students.


21) Greener Good Market at Magazine Beach

When: Sat. 5/2

Where: Cambridge

Cost: Free

Info: Shop sustainably and for a good cause at this Greener Good Market at Magazine Beach. There will be local vendors selling handmade goods that are crafted from sustainable materials like upcycled art, zero-waste home essentials, and more. Find unique treasures and help keep the Earth clean.


22) Makers in Bloom: Boston Women’s Market at The Connector

When: Sat. 5/2

Where: Financial District

Cost: Free

Info: Boston Women’s Market will be popping up at The Connector at Winthrop Center. Come shop for handmade goods, especially for Mother’s Day, as you sip on a fun bev and munch on light bites. There will be fun activities like face painting and tote decorating too.


23) Spring Garden Day

When: Sat. 5/2

Where: Somerville 

Cost: Free

Info: Join the Somerville Community Growing Center for a fun spring day. Pot an herb plant, bring or take home seeds, and make some art. There will also be dance performances, a Maypole dance, and other fun surprises.


24) Cupcake Picnic

When: Sat. 5/2

Where: Watertown

Cost: Free

Info: Visit the Watertown Library for a sweet party as Cake4Kids celebrates its 5th year as a Greater Boston Area chapter and its 100,000th cake delivery. There will be free cookies, cupcakes for sale, musical chairs, and other fun activities for everyone.


25) Celebrate Public Art

When: Sat. 5/2

Where: Rose Kennedy Greenway

Cost: Free

Info: Join neighbors at Armenian Heritage Park to celebrate public art. Meet in front of the Abstract Sculpture which annually reconfigures into a new shape. Then, walk with new friends and participate in World Labyrinth Day: Walking As One in Peace and Harmony at the same time as folks in San Francisco, Rome, Barcelona, and more. 


26) Community on the Browne House Lawn

When: Sat. 5/2

Where: Watertown

Cost: Free

Info: Head to the Browne House for a community day on the lawn. There will be live music and lawn games, as well as table talks with local organizations. Learn about the history of Watertown and take a tour of the oldest house in the neighborhood.


27) Gibson Point Spring Market

When: Sat. 5/2

Where: Revere

Cost: Free

Info: Head to Gibson Point for a spring market right by the water. Shop small and local from businesses selling handmade goods, home decor, and more. You’ll find the perfect gift for yourself or a loved one as you shop with a view.


28) Boston Open Market

When: Saturdays, starting Sat. 5/2

Where: Boston Common

Cost: Free

Info: One of Boston’s beloved outdoor markets is returning for the 2026 season. Stroll along Boylston right by the Public Garden and the Common to shop from over 50 local makers, artists, and curated vintage dealers. You’ll leave with a new treasure in hand for yourself or a loved one.


29) Seaport Summer Market

When: Saturdays, starting Sat. 5/2

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.


30) SoWa Art Walk 2026

When: Sat. 5/2 - Sun. 5/3

Where: South End

Cost: Free

Info: Check out the annual SoWa Art Walk. Enjoy three days of celebrating art and exploring the galleries at SoWa. Meet the artists, chat with other art-lovers, shop for new pieces, and learn about creative processes at this open studios event.


31) Somerville Open Studios 2026

When: Sat. 5/2 - Sun. 5/3

Where: Somerville

Cost: Free

Info: Check out the 27th Annual Somerville Open Studios. Wander around the neighborhood and connect with over 400 artists who will be showcasing their studios and artwork. Explore the creativity of the community and feel inspired.


32) The Elks Lodge Bazaar: Spring Season Finale

When: Sat. 5/2 - Sun. 5/3

Where: Brighton

Cost: Free

Info: Head to the Brighton Bazaar’s spring season finale at the Elks Lodge – they won’t be returning to this venue until the fall. Dance to the tunes of the DJ and bring your pup while you peruse for some handmade goods and other fun trinkets from over 100 small businesses.


33) Boston Spring Market

When: Sat. 5/2 - Sun. 5/3

Where: South End

Cost: $6

Info: Stop by the Boston Spring market at SoWa Power Station. There will be plenty of local artists who will be selling art, handmade goods, clothes, decor, and so much more. Upgrade your ticket for a free, customizable tote with pop-up DIY stations to store all your new finds.


34) Greenway Artisan Market

When: Saturdays and Sundays, starting Sat. 5/2

Where: Rose Kennedy Greenway

Cost: Free

Info: The Greenway Artisan Market returns with over 50 vendors popping right along the Greenway. Shop for handmade goods and new gifts, and then take a ride on the carousel. Make sure to stop by the waterfront after your stroll.


35) Bachata by the River: Summer Kickoff 

When: Sun. 5/3

Where: Cambridge

Cost: Free

Info: The return of outdoor dance party season is here. Come enjoy beginner-friendly salsa and bachata lessons. Then, meet new friends during the social dance right along the river as the sun sets. 


36) Ukrainian Boutique & Delicious Eats 

When: Sun. 5/3

Where: Jamaica Plain

Cost: Free

Info: Experience Ukrainian culture firsthand by checking out this Ukrainian festival. There will be traditional foods and other delicious eats, as well as handmade gifts and crafts. Proceeds support children who have been orphaned by the war in Ukraine.


37) SoWa Open Market 2026

When: Sundays, starting Sun. 5/3

Where: Somerville

Cost: Free

Info: One of Boston’s most beloved outdoor markets is returning every Sunday. Shop for fresh produce, yummy sweet treats, and handmade goods at SoWa Open Market. There will be food trucks, live entertainment, and more. Don’t forget to check out the studios, galleries, and vintage market while you’re there.


38) Seaport Sweat 2026

When: Mondays to Saturdays, starting Mon. 5/4

Where: Seaport

Cost: Free

Info: Get your body moving and break a sweat with free fitness classes in Seaport. Enjoy classes like pilates and zumba to yoga and strength training. Make new friends and feel the burn to the tunes of a DJ too.


39) Drinking + Drawing at Zone 3

When: Tuesdays, 5/5 & 5/12

Where: Allston

Cost: Free

Info: RSVP to secure your spot to this neighborhood art party. Enjoy complimentary pizza and drinks as you make art and enjoy a guided lesson with a local artist. From puppet-making to sketching and beyond, you’ll have a chance to explore your imagination with new friends.


40) Seaport Sketch

When: Tuesdays, 5/5 & 5/19

Where: Seaport

Cost: Free

Info: Get sketchin’ and unlock your creativity with guided lessons from local artists. Doodle, draw, and more with new friends as you enjoy a live DJ or some live music as you practice your art skills!


41) South End Spring Stroll

When: Wed. 5/6

Where: South End

Cost: Free

Info: There’s nothing like a relaxing walk while exploring local businesses. Check out the South End Spring Stroll where you can enjoy special deals, samples, and more at retailers, restaurants, and art galleries/organizations. Come learn about this neighborhood and connect with neighbors.


42) Everybody Dance Now: Outdoor Drop-In Dance Classes

When: Wednesdays, starting Wed. 5/6

Where: Allston

Cost: $10+

Info: Learn how to country line dance and master some fun choreography with new friends at the Grove in Allston. At this outdoor dance series, you can enjoy weekly easy-to-follow lessons by local organizations like 617 Country and Diva Dance. 


43) JoyWalk: Fenway Cultural District Art Crawl

When: Thu. 5/7

Where: Fenway

Cost: Free

Info: Celebrate the talents and creativity of the Fenway neighborhood by enjoying free admission to places like the MFA, MAAM, the Gardner Museum, the Fenway Gallery, Fenway Studios, and so much more. Connect with the community and meet new friends. 


44) Boston’s National Bike to Work Day Festival

When: Thu. 5/7

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 with neighbors and new friends.


45) South Boston Spring Stroll

When: Thu. 5/7

Where: Southie

Cost: Free

Info: Explore the local businesses in Southie by taking a stroll. Restaurants and retailers will be offering up discounts, samples, and other promotions. Plus, there will be live music, complimentary pedicab rides, and more. 


46) Noche Electrica: Salsa Dance Social 

When: Thu. 5/7

Where: Roslindale

Cost: $5

Info: Make new friends while learning how to salsa dance. There will be an intro class for those with little to no experience. Then, you can practice your moves at the high-energy dance social right after. No partner necessary!


47) BINGO! Night 

When: Thu. 5/7

Where: Back Bay

Cost: $10

Info: You’re never too old to enjoy a fun game of Bingo. Head to Trident where there will be a seat, a card, and a fun marker waiting for you with your ticket. There will be food and beverages available for purchase as you see if luck is on your side to win some prizes.


48) Fashionably LATE Thursdays

When: Thursdays, starting Thu. 5/7

Where: Beacon Hill

Cost: Free

Info: Grab a drink in the beautiful lobby of the Liberty Hotel and stay for the fun fashion shows that happen later in the evening. Models will be showcasing local and elite fashion brands as they strut their looks down the escalators and hallways.


49) Vinyl & Vino at Impeccable Art Gallery

When: Thursdays, starting Thu. 5/7

Where: South End

Cost: $10

Info: Mix and mingle with new friends at these vibey evenings at a local art gallery. Bring a vinyl and your favorite vino that you can share with the crowd. You’ll have a chance to spin a 10-15 minute set while you learn about the art on display and connect with others.


50) Downtown Boston Arts Market

When: Thursdays and Fridays, starting Thu. 5/7

Where: Downtown Crossing

Cost: Free

Info: Downtown Boston Arts Market is partnering with your favorite Select Markets to curate a rotating lineup of talented vendors. Stop by every Thursday and Friday in Downtown Crossing to connect with local artists, businesses, and more.


51) Boston Landing Movie Night featuring ‘Empire Records’

When: Fri. 5/8

Where: Boston Landing

Cost: Free

Info: Catch a free screening of the cult-classic film ‘Empire Records’ at Roadrunner. Grab some complimentary popcorn while supplies last and get there early for some DJ tunes during the pre-party. There will be food and drinks available for purchase to elevate your night too.


52) Free Outdoor Meditation @ Boston Public Garden

When: Fri. 5/8

Where: Boston Public Garden

Cost: Free

Info: Take a second and relax. Reconnect with your body, your mind, and the world by enjoying this free guided outdoor meditation in the Boston Public Garden. Feel the energy and rejuvenation as you sit amongst 30-50 neighbors.


53) 15th Annual Somerville PorchFest

When: Sat. 5/9

Where: Somerville

Cost: Free

Info: Don’t miss one of Greater Boston’s best traditions: PorchFest. Get ready to dance all day, meet new friends, and discover new music as local artists take the stage as they perform on porches, in driveways, in garages, and more. Bring your friends and enjoy this hyper-local music festival.


54) Vintage Block Party

When: Sat. 5/9

Where: Harvard Square

Cost: Free

Info: The Attic and Back & Forth Flea are teaming up to bring a one-day vintage block party in the heart of Harvard Square. Spend the afternoon looking for unique vintage treasures from over 15 vendors. Come amp up your style with one-of-a-kind pieces from local businesses.


55) PorchFest at Pemberton Farms

When: Sat. 5/9

Where: Cambridge

Cost: Free

Info: Cambridge is joining the Somerville PorchFest fun. Head to Pemberton Farms for a mini music fest featuring local artists who will be taking the stage. Dance with new friends and discover new music.


56) PorchFest Afterparty: Battle of the Bands

When: Sat. 5/9

Where: Cambridge

Cost: Free

Info: The PorchFest vibes aren’t stopping in Somerville. Head to Remnant Satellite and Portico Brewing for an afterparty of the ages. Local groups will be taking the stage at both locations, so grab a brew and get ready for a battle of the bands.


57) Brewery Prom Night

When: Sat. 5/9

Where: Cambridge Crossing

Cost: Free

Info: Head to Lamplighter CX for an evening of prom fun. Dress up, bring a corsage, and ask your special someone to be your date as you dance under the twinkling lights of the Enchanted Forest theme. There will be drink specials and other fun surprises. 


58) City Farm Fest: Seedling Sale & Celebration

When: Sat. 5/9

Where: Roxbury

Cost: Free

Info: Celebrate the Earth and community gardening at City Farm Fest. Get your soil tested for free to make sure your garden is healthy. Shop for veggies, herbs, flowers, and fruit trees. Munch on complimentary Jamaican food, listen to live music, make some art, and so much more.


59) Gibson and the Garden

When: Sat. 5/9

Where: Boston Public Garden

Cost: Free

Info: Dress in your Victorian-inspired outfit and join a formal promenade at the Public Garden. Then, walk to the Gibson House with new friends for an open house featuring a special exhibition. 


60) Celebrate International Hummus Day 

When: Sat. 5/9

Where: Beacon Hill

Cost: Free

Info: Happy International Hummus Day. Celebrate the 2nd Annual Celebration at the Hummus Shop which will be serving up 1000 pounds of homemade fresh hummus for all. Come sample some of this yummy spread and hang out on the patio.


61) 5th Annual Quincy Multicultural Festival 

When: Sat. 5/9

Where: Quincy

Cost: Free

Info: Bring your friends, family, and pets to this multicultural festival. Enjoy live performances, food from around the world, art-making for all, cultural tables and displays, and a vendor market. Come experience the diversity of the world and the Greater Boston area at this celebration. 


62) Lion Dance and Kung Fu Traditions Come Alive

When: Sat. 5/9

Where: Dorchester

Cost: Free

Info: Celebrate Asian American and Pacific Islander Heritage Month at the JFK Library. There will be free admission, art-making stations, special performances, and other fun surprises for everyone to enjoy. 


63) 2000s Throwback Night at West End Johnnie’s 

When: Sat. 5/9

Where: West End

Cost: Free

Info: Throw it back to your favorite 2000s hits at West End Johnnie’s. Get ready to dance the night away in true Y2K style featuring songs by Kesha, Pitbull, Flo Rida, and more. Bring your friends and tear up the dance floor.


64) Boston Women's Market at Assembly Row

When: Sat. 5/9

Where: Assembly Row

Cost: Free

Info: Boston Women’s Market will be bringing a diverse lineup of over 30 women-owned small businesses to Assembly Row. Come shop for handmade goods, yummy snacks, and other unique items. 


65) 22nd Annual Union Square Farmers Market

When: Saturdays, starting Sat. 5/9

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. 


66) Duckling Day

When: Sun. 5/10

Where: Boston Common

Cost: Free

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.


67) Lilac Sunday at the Arnold Arboretum

When: Sun. 5/10

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.


68) FOUND Vintage Market at Tall Ship

When: Sun. 5/10

Where: Charlestown

Cost: Free

Info: The Tall Ship is officially open for the season. Grab a drink on this giant boat on the Harbor and shop from over 60 vintage and sustainable-style curators. Find a hidden treasure with a stunning skyline view on the waterfront.


69) Somerville Community Bike Ride

When: Tue. 5/12

Where: Somerville

Cost: Free

Info: Hop on your bike and meet new friends during this inclusive community bike ride from Conway Park through Davis Square. If you don’t have a bike, no worries since BlueBike codes will be provided!


70) Swing in the Square

When: Wednesdays, starting Wed. 5/13

Where: Roslindale

Cost: Free

Info: Join free dance workshops and learn different swing styles like Lindy Hop, East Coast Swing, and West Coast Swing. There will be a one hour beginner-friendly lesson and then a social dance to follow, so you can practice your moves with experienced dancers. Get groovy outside!


71) Open Studios Block Party Allston

When: Thu. 5/14

Where: Allston

Cost: Free

Info: A block party is coming to Allston. Head to Alchemy Station where you can enjoy studio tours with artists-in-residence. Learn about unique art processes and meet creators. There will also be live music by the Boston Jazz Foundation.


72) Baroque Remix: Old Music, New Stories

When: Thu. 5/14

Where: Dorchester

Cost: Free

Info: The historic Strand Theatre is hosting a fun, playful concert inspired by Bach and his contemporaries. Reimagine classical music with modern stories, entertaining humor, and even a few pop songs woven throughout the mix.


73) Roslindale Film Society: ‘Minority Report’

When: Thu. 5/14

Where: Roslindale

Cost: $7-10

Info: Join the Roslindale Film Society for a community screening of ‘Minority Report’ at Square Root Cafe. Beer, wine, and food will be available for purchase to elevate your watch experience. Come meet new friends at this get-together.


74) Rosé Rumble 2026

When: Thu. 5/14

Where: Cambridge

Cost: $10

Info: First Street Market is hosting a special showdown of the best rosé. With your ticket, you’ll get to sample dozens of pink wines from around the world. Don’t forget to come dressed in pink for a shot at a prize. Salud!


75) Allstonway Welcome Weekend

When: Thu. 5/14 - Sat. 5/16

Where: Allston

Cost: Free

Info: Check out Allstonway, a new public space at the Enterprise Research Campus. Come celebrate its official opening with live music, an outdoor cocktail bar, a pop-up printmaking station, food trucks, and so much more.


76) Friday Films: ‘The Boy and the Heron’

When: Fri. 5/15

Where: Roxbury

Cost: Free

Info: Join the Parker Hill Branch Public Library for a special screening of ‘The Boy and the Heron.’ Catch Miyazaki’s most recent Studio Ghibli film and be transported into a new world built on intricate design and storytelling.


77) Dialogue Nights

When: Fri. 5/15

Where: Mission Hill

Cost: Free

Info: Stop by the Ikeda Center for an evening of introspective dialogue between 20- and 30-somethings. There will be icebreakers, small group discussions, and open reflections. Food will be provided while supplies last.


78) ArtSEA: Beads and Boardgames

When: Fri. 5/15

Where: Seaport

Cost: Free

Info: Boston Gaymers and ArtSEA are bringing neighbors an evening of community connection through art-making and games. Come make anchor cords with beads and charms, or make new friends while playing your favorite tabletop board games. Light refreshments will be provided too.


79) Copley Square Farmers Market

When: Tuesdays and Fridays, starting Fri. 5/15

Where: Copley Square

Cost: Free

Info: Find some of the freshest produce, blooming flowers, hyperlocal goods and sweet treats, and other fun treasures at this beloved farmers market in the heart of Copley Square. You’ll find new items and have the chance to connect with local businesses in the center of the city.


80) 2nd Annual Panda Fest Boston 

When: Fri. 5/15 - Sun. 5/17

Where: Allston

Cost: $10+

Info: Panda Fest is bigger and better than ever. This year, the 2nd annual Panda Fest will be taking place at Harvard’s Ohiri Field. Come explore the diversity of Asian cuisine, art, and culture while enjoying panda-themed attractions and art.


81) La CASA Opening Weekend

When: Fri. 5/15 - Sun. 5/17

Where: South End

Cost: Free

Info: La CASA is a new cultural home for LatinX arts, activism, and advocacy. Come celebrate its official opening with live music, music and dance workshops, art-making activities, tours of the new space, and even an evening dance party for all ages.


82) Franklin Park Kite & Bike Festival

When: Sat. 5/16

Where: Roxbury

Cost: Free

Info: Participate in this 50+ year old tradition at Franklin Park! Welcome spring by making, buying, or flying your own kite. Grab a bite from a local food truck, enjoy a picnic on the grass, and get your bike repaired too. Connect with neighbors during opening day.


83) Roslindale Jazz Festival

When: Sat. 5/16

Where: Roslindale

Cost: Free

Info: Roslindale is hosting an afternoon full of free, live music on two stages in Adams Park and Birch Street Plaza. Experience the talented lineup of local bands, move your body to soulful tunes, and connect with neighbors over great music.


84) Gays for Patsy Queer Country Social

When: Sat. 5/16

Where: Jamaica Plain

Cost: Free

Info: It’s the second-to-last queer country dance social before the spring season ends. Join this queer, intergenerational dance space where all experience levels are welcome. Come two-step, waltz, line dance, and more while connecting with new friends.


85) Quincy’s Classic Rock Concert

When: Sat. 5/16

Where: Quincy

Cost: Free

Info: Quincy is hosting its very own mini Woodstock. Come dance and enjoy the music of three tribute bands who will be playing iconic songs by The Rolling Stones, Pat Benatar, and more. There will be food trucks and a bar on-site!


86) Watertown PorchFest 2026

When: Sat. 5/16

Where: Watertown

Cost: Free

Info: Happy PorchFest season. Head to Watertown for live music all across the neighborhood. Explore different genres and talented local musicians as they put on a show along driveways, patios, porches, and more.


87) 4th Annual Greater Roxbury Book Fair 

When: Sat. 5/16

Where: Roxbury

Cost: Free

Info: Check out the 4th Annual Greater Roxbury Book Fair. Shop from pop-up indie booksellers for your next TBR. Celebrate the power of storytelling and creativity with other book lovers. There will be food trucks, author signings, art vendors, and more.


88) Kölsch Service at Aeronaut

When: Sat. 5/16

Where: Somerville

Cost: $10

Info: Grab a ticket for a traditional Kölsch service at Aeronaut. Included with your ticket is a special glass and a seat at the table for this pouring service where you signal servers to stop by placing a coaster over your cup. Each glass is $9, so come get ready to drink!


89) Inman Eats & Crafts 2026

When: Sun. 5/17

Where: Inman Square

Cost: Free

Info: Inman Square is hosting its annual neighborhood festival. Get ready to explore the quaint streets of East Cambridge while supporting local businesses. Relax at the beer garden, listen to live music, and shop for some art. If you want to purchase food from one of the restaurants/eateries, make sure to purchase Inman Bucks beforehand.


90) 2026 Watertown Dam Herring Festival

When: Sun. 5/17

Where: Watertown

Cost: Free

Info: If you’re a nature lover and/or bird enthusiast, check out the annual Watertown Dam Herring Festival. Bring your friends and family to learn about the fish species that spawn around the Charles, as well as the history of and current cultural practices of Indigenous food sovereignty. There will be food and art vendors, a print-making station, performances, and more.


91) Third Thursdays at the MFA

When: Thu. 5/21

Where: Fenway

Cost: $5

Info: Enjoy special $5 admission to the MFA. Celebrate spring and explore the galleries on display. There will be spotlight talks, drawing in the galleries, a Nick Shea portrait pop-up, live music, and more.


92) Sam Sessions Music Fest

When: Fri. 5/22 - Sun. 5/24

Where: South End

Cost: Free

Info: The annual Sam Sessions Music Fest has grown to two stages in the beer garden this year! Throughout the weekend, you can grab a brew and dance to the tunes of local musicians. Summer is so close — cheers to good drinks, great music, and even better vibes with neighbors.


93) Small Mart at Crystal Ballroom

When: Sat. 5/23

Where: Davis Square

Cost: Free

Info: Shop for one-of-a-kind gifts at this beloved pop-up market in the Crystal Ballroom. Grab a drink and shop from over 40 artisans and vintage vendors under the twinkling lights of giant chandeliers.


94) AAPI Heritage Celebration

When: Sat. 5/23

Where: Malden

Cost: Free

Info: Head to the Malden Senior Center for an inspiring afternoon of speeches and talks to celebrate AAPI heritage. There will be panel speakers of East Asian, Southeast Asian, and South Asian descent who will be sharing their stories. There will also be delicious eats and cultural performances. 


95) ‘Top Gun Maverick’ Screening

When: Sat. 5/23

Where: Back Bay

Cost: Free

Info: Get cozy at Trident Booksellers and Cafe. Grab a bite to eat or sip on a warm drink as you watch a free screening of ‘Top Gun Maverick.’ This is the perfect, low-energy neighborhood event for a chill weekend in.


96) Festival Viva Chile Boston 2026

When: Sat. 5/23

Where: East Boston

Cost: $0+

Info: Come celebrate Chilean culture at the 12th Annual Viva Chile Boston. Entrance is free, but please donate if you’re able to support this local nonprofit. Enjoy cultural dance and music performances, traditional Chilean food, and connect with the community.


97) The Big Gig: Spring Music Festival & Market

When: Sat. 5/23 - Sun. 5/24

Where: Brighton

Cost: Free

Info: The Charles River Speedway is hosting its 3rd Annual Music Festival and Art Market. Come enjoy two days of ten local music acts while shopping from over 100 small businesses. Grab a drink or a snack and get ready to discover local talent.


98) Fenway Outdoor Vintage Festival at Time Out

When: Sat. 5/23 - Sun. 5/24

Where: Fenway

Cost: Free

Info: Jon Select Markets for a two-day outdoor vintage festival featuring over 30 vendors who will be showcasing unique goods. Throw it back to Y2K, grab a free fizzy bev, get a temp tat or tooth gem, and so much more.


99) Black Owned Bos. Market

When: Sun. 5/24

Where: Seaport

Cost: Free

Info: Seaport x Black Owned Bos. Market is returning for its 7th season! Come celebrate and join the party at the May Market: Rhythm and Blooms. While you support Black-owned businesses, you can enjoy live music, grab a bite from a food truck, and enjoy activities that celebrate music and spring.


100) Apéro au Soleil: Patio Kickoff Party

When: Sun. 5/24

Where: Cambridge

Cost: Free

Info: Celebrate patio season with sunny weather and great vibes at Remnant Satellite’s outdoor space. Sip on Aperol spritzes, Hugo spritzes, and other fun summery drinks while soaking up the sun with friends.


101) MFA Open House: Memorial Day

When: Mon. 5/25

Where: Fenway

Cost: Free

Info: Enjoy free admission to the MFA on Memorial Day! There will be a puppet takeover by the Puppet Showcase Theater. Make your own puppet, explore the galleries, take a tour with a puppet guide, and more!


102) Memorial Day: Free Admission to ICA Boston

When: Mon. 5/25

Where: Seaport

Cost: Free

Info: The ICA is offering free admission for Memorial Day. Reserve your ticket in advance, so you can explore contemporary exhibits on display while enjoying beautiful skyline views of the city right along the waterfront.


103) Game Night at Fenway Community Center

When: Wed. 5/27

Where: Fenway

Cost: Free

Info: Need a midweek pick-me-up? Head to the Fenway Community Center for an evening of board games and card games with new friends. Come bring your favorite tabletop game to share with the group and bond with neighbors.


104) Harvard Art Museums at Night

When: Thu. 5/28

Where: Harvard Square

Cost: Free

Info: Your favorite after-hours museum party is back on the last Thursday of the month. Dance to DJ tunes, make some art, and explore over 50 galleries. There will also be food and drinks available for purchase by local vendors.


105) ‘Lord of the Rings’ Trivia Night

When: Fri. 5/29

Where: Downtown

Cost: Free

Info: Do you have what it takes to claim your previous? Put your LOTR knowledge to the test at Boston Public Market for a shot at some prizes. Don’t forget to grab a snack and a drink from one of the vendors on-site as you test your Middle-Earth skills.


106) Greenway Food Truck and Fitness Festival

When: Sat. 5/30

Where: Revere

Cost: Free

Info: There’s nothing like the annual Greenway Food Truck and Fitness Festival. Enjoy free fitness classes and shop from local art vendors. There will also be 15 food trucks serving up yummy snacks and sweet treats for a post-workout snack. Don’t forget to ride the carousel, dance to a DJ, and more.


107) Revere Beach Kite Festival

When: Sat. 5/30

Where: Revere

Cost: Free

Info: We are on the verge of entering official beach season. Before the sun’s rays blaze upon us, you can enjoy the breeze at the annual Kite Festival. Build, decorate, and fly kites right next to the ocean. There will also be live music, professional kite flyers, and other family-friendly activities.


108) 2nd Annual WBUR Festival Street Fair

When: Sat. 5/30

Where: Allston

Cost: Free

Info: Join WBUR for their second Festival Street Fair right along the Charles. Shop for hidden treasures at the FOUND market featuring 80+ vendors. There will also be live music, dance lessons for all ages, food trucks, and a community mural that you’re welcome to participate in!


109) Be-InFormed Boston

When: Sat. 5/30

Where: Boston Common

Cost: Free

Info: This festival is a little different. Come ready to learn, to talk, and to lean into discomfort to build connection. Stop by the Common where there will be multiple conversation stations that cover important topics like abortion, mental health, and racism. There will be a facilitator who will provide a 20-minute talk, and then participants are free to respond and converse with each other. Get ready to leave with a different perspective.


110) Aeronaut’s 12th Anniversary

When: Sat. 5/30

Where: Somerville

Cost: Free

Info: Happy 12th birthday to the beloved Aeronaut. Come join the celebration with free birthday cake, brewery-themed party games, and live music. Don’t forget to try a special 12-year anniversary brew after making your rounds around your favorite taps.


111) Splendoria - Free Bouquets

When: Sat. 5/30

Where: Seaport

Cost: Free

Info: Come explore the beautiful floral installations at the Superette. It’s a little oasis away from the hustle and bustle of Seaport where you can rest and relax. And on the last Saturday of every month, you can grab a free bouquet! Don’t forget to sign up on the Seaport Insider app to redeem this special offer.


112) Malden Porchfest 2026

When: Sat. 5/30

Where: Malden

Cost: Free

Info: Kick off Porchfest season by strolling around Malden. Discover local talent by listening and dancing to music around the neighborhood’s porches, driveways, and stoops. Bring your friends and family to enjoy this music festival. 


113) The Ardsley Women’s Sports & Health Market

When: Sat. 5/30

Where: Arsenal Yards

Cost: Free

Info: Head to Arsenal Yards for a market that centers on women’s health, wellness, and empowerment. Connect with local organizations, shop from women-led vendors, and explore different fitness and recovery stations. 


114) Free Ferry Weekend

When: Sat. 5/30 - Sun. 5/31

Where: Long Wharf

Cost: Free

Info: Summer is almost here! Enjoy the outdoors and the Greater Boston area by hopping on a ferry to Georges Island. Hike one of the trails, take in the skyline views, relax on the beach while enjoying the picnic, and explore. 


115) 41st Annual Mayfair in Harvard Square

When: Sun. 5/31

Where: Harvard Square

Cost: Free

Info: Don’t miss the 41st Annual Mayfair, one of Greater Boston’s biggest spring festivals. Harvard Square will be coming alive with live music, artistic performances, beer gardens, creative installations, and vendors. You can celebrate cultures from around the world, stop by the 4th Annual Asian Street Food and Music Festival, and listen to folk tunes at Club Passim.


116) Strides for Action

When: Sun. 5/31

Where: Boston Common

Cost: Free

Info: Join Fenway Health’s annual 5K walk and run to support queer health, prevention, and treatment. This event is free to join, so please fundraise, donate, and tell your community about how to support LGBTQIA+ health services. This year marks the 40th anniversary of the movement that began AIDS Walk Boston, so put on your sneakers and honor the legacy of queer advocacy.


117) Polish Fest Boston 2026

When: Sun. 5/31

Where: Dorchester

Cost: Free

Info: Stop by the annual Polish Fest to learn about Polish culture. Celebrate Boston’s Polish-American community with family-friendly activities, live music, cultural performances, a vendor market, and of course, traditional food.

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