Wednesday, May 01, 2024 9:00a -
Friday, May 31, 2024 11:00p

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Boston, MA

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Art, Date Idea, Drinks, Festivals & Fairs, Food, Good for Groups, Meetup, Music, Outside, Party, Photoworthy, Sports & Active Life

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May is the month when the city comes back to life after a chilly slumber. Flowers are blooming, the warm weather is lingering, and more people are out and about. Take advantage of this beautiful month with these must-do events around Boston.

Events are listed in chronological order. 

By Yelena Nicolle Salvador

1) Kendall After Party

When: Wed. 5/1

Where: Kendall Square

Info: Had a long work day? Ready to mingle? Stop by MIT Open Space for food popups with empanadas, craft stations, live music and drinks by Rebel Rebel and Remnant. Relax and unwind at this event for free.

2) Boston Design Week

When: Wed. 5/1 - Mon. 5/5

Where: Around Boston

Info: Listen to speakers and walk around different exhibits that showcase all avenues of art: architecture, landscape design, social impact design, handmade design, and more.

3) Independent Film Festival Boston

When: Wed. 5/1 - Wed. 5/8

Where: Theaters around Boston

Info: Bring your friends and immerse yourself in new and experimental worlds created by cutting-edge storytellers. IFF Boston is the largest film festival in New England – so get ready to be entertained!

4) Seaport Sweat 2024: Free Outdoor Fitness Series

When: Mondays to Saturdays, starting Wed. 5/1

Where: Seaport 

Info: It’s back for its ninth season! Break a sweat, prepare for summer, feel good, try new workouts, and get some sun – all with these guided classes by award-winning instructors and pump up beats.

5) Ghibliotheque

When: All month long, starting Wed. 5/1

Where: Brookline

Info: Visit this beloved local independent movie theater and see its beautiful expansion with new screens and lobbies – all while celebrating the breathtaking worlds of Hayao Miyazaki! This month-long screening event will feature Studio Ghibli films in 35mm.

6) Free First Thursdays at the Isabella Stewart Gardner Museum

When: Thurs. 5/2

Where: Fenway

Info: Step into the magic of the Gardner, which has an inner courtyard of flowers and a collection of work from around the world. These free tickets usually sell out within a few days, so mark your calendars two weeks before the first Thursday of the month when these tickets go live (May 23!).

7) Fresh Classics Shop n Sip

When: Thurs. 5/2

Where: Central Square

Info: Shop vintage, art, and more at this night market. Once you're done, stay for a late night out with DJ beats, drinks, and a party vibe.

8) Alvin Ailey American Dance Theater

When: Thurs. 5/2 - Sun. 5/5

Where: Chinatown

Info: Take in the storytelling of contemporary dance that depicts the facets of Black American life, culture, and history at one of these performances. You’ll feel inspired after watching the graceful movements of these dancers come to life.

9) Fenway’s Got Talent

When: Thurs. 5/2 and Thurs. 5/9

Where: Fenway

Info: Have a laugh and enjoy the entertainment or take the stage at Time Out for a chance to win two tickets to Boston Calling. Don’t forget to grab a bite at this food hall with many delicious offerings and refreshing drinks!

10) Free Thursdays at the ICA

When: Thursdays, starting 5/2

Where: Seaport

Info: Visit this museum of contemporary art with amazing views of the waterfront. Every Thursday, the ICA offers free admission at night, so don’t forget to reserve your timed tickets for entry to watch the sun set and see new art.

11) Cinco de Mayo in Downtown

When: Fri. 5/3

Where: Downtown

Info: Celebrate Cinco de Mayo early in Downtown Crossing. Listen to Mexican folk music and watch traditional dance. There will also be a crafts fair and more!

12) Boston Calling Night

When: Fri. 5/3

Where: Downtown

Info: Can’t make Boston Calling? Want to hear the music early? Look no further since artists from the music festival will be playing tunes and DJs will be dropping beats at this event for free.

13) Rhythm N’ Spice Hot Sauce Fest

When: Sat. 5/4

Where: Kendall Square

Info: Your taste buds will burn ablaze. Taste the spiciest hot sauces alongside yummy food popups, live music, and other performances.

14) Picnic Social for 20’s and 30’s

When: Sat. 5/4

Where: Boston Garden

Info: Grab a blanket and some snacks and head to the Boston Garden to meet some new friends. Watch the swan boats, soak up the sun, and mingle with folks from Boston who are looking for community.

15) 6 Beers for 6 Years at Remnant

When: Sat. 5/4

Where: Somerville

Info: Our fave, Remnant Brewing, is turning 6 years old this weekend! Come celebrate in their beer garden as they launch 6 brews in honor of their birthday. 

16) The Overlook Grand Opening Fiesta

When: Sat. 5/4

Where: Seaport

Info: Legal Sea Foods Harborside is opening their revamped bar and lounge! Grab a ticket and you’ll get access to some light bites, drinks, and spectacular views on their rooftop that overlooks the harbor.

17) The Tall Ship Boston 2024 Opening Weekend

When: Sat. 5/4 - Sun. 5/5

Where: East Boston

Info: A two-day kickoff event to mark the beginning of Tall Ship season! Watch the Derby or celebrate Cinco de Mayo. Enjoy drinks with spectacular waterfront views, giveaways, and food popups.

18) Boston Theater Marathon XXVI

When: Sun. 5/5

Where: Allston

Info: 50 ten-minute plays by 50 different New England playwrights and performers. Immerse yourself in the imaginations of talented artists at this annual event. 

19) 39th Annual Mayfair in Harvard Square

When: Sun. 5/5

Where: Harvard Square

Info: Celebrate spring with this multicultural festival full of free samples, live music, and other performances. There will be a Cinco de Mayo party, three beer gardens, and an Asian Street Food and Music Festival too! Come with empty bellies and leave full and happy.

20) Open Streets 2024: Dorchester

When: Sun. 5/5

Where: Dorchester

Info: Kick off the Open Streets Boston season at Dorchester. Stroll along car-free streets full of live music, food stands, and other family-friendly experiences.

21) SoWa Open Market

When: Weekly, starting Sun. 5/5

Where: South End

Info: Tis the season for outdoor markets. Sowa Open Market is one of the largest open-air farmer and artist markets in the city. Look at beautiful art with snacks from food trucks and a chilling drink too. 

22) The Boston Parks Summer Fitness Series

When: Daily, starting Sun. 5/5

Where: Parks around Boston

Info: Take advantage of the great weather and enjoy the outdoors while getting your heart rate up at one of these free workout classes. 

23) MIT Museum After Dark

When: Thurs. 5/9

Where: Kendall Square

Info: Learn about science, enjoy hands-on demonstrations, listen to live music, and explore the MIT Museum with a drink in hand. This 21+ event is a fun time to see this museum in a different light.

24) Frog Pond Yoga

When: Thursdays, starting 5/9

Where: Boston Common

Info: Inhale and exhale, find peace after a long day, and enjoy guided yoga in the heart of the city at the Frog Pond for free.

25) MFA Late Nites

When: Fri. 5/10

Where: Fenway

Info: Explore art galleries, have a drink, make some art, and dance the night away – all in the beautiful MFA during late night hours. Grab a ticket and get inspired by the ‘Dress Up’ and ‘Hallyu! The Korean Wave’ exhibits. Wear sparkles or whatever makes you feel good and enjoy panels and popup experiences too.

26) Hood Park Spring Fest

When: Sat. 5/11 

Where: Charlestown

Info: Spring is here! Say hello to the blooms and the warm weather with a petting zoo, food trucks, crafts, yard games, a splash pond, and more – there’s something for everyone to enjoy.

27) Somerville PorchFest 2024

When: Sat. 5/11 

Where: Somerville

Info: Take a stroll through town on this beloved day and you’ll be surrounded by music and endless tunes. Locals perform on their porches, sidewalks, and in front of buildings. Show them some love and cheer them on.

28) LadiesCon 2024

When: Sat. 5/11 

Where: Somerville

Info: Enjoy a free day that celebrates the boss energy of all the amazing women in Boston. This day of pop culture fun features work by women in art, comics, cosplay, and more. Stay awhile for this one since you’ll be transported to a world that highlights the voices of women, queer folks, and BIPOC.

29) Small Mart Porchfest Market

When: Sat. 5/11

Where: Davis Square

Info: Shop ‘til you drop at this artisan market that highlights local businesses. Grab a drink or mocktail and wander around the many booths that have everything you could ever want.

30) Spring Fling

When: Sat. 5/11

Where: Seaport

Info: It’s a party over here at the waterfront. Dress your best and snap a pic at the photo booth for a chance to win Seaport swag. When you’re done with the photo ops, dance all afternoon with a drink and some sweet treats in hand.

31) GyroFest

When: Sat. 5/11 - Sun. 5/12

Where: Somerville

Info: Come hungry to taste the foods of Greece. There will be gyro, chicken kabobs, baklava, and more!

32) Duckling Day

When: Sun. 5/12

Where: Boston Common

Info: One of the cutest Boston traditions to date, Duckling Day will put a smile on your face. Watch a parade of lil humans dressed as fuzzy ducklings and enjoy the festivities of this family-friendly event in celebration of the famous book, ‘Make Way for Ducklings’ by Robert McCloskey. 

33) Lilac Sunday at the Arnold Arboretum

When: Sun. 5/12

Where: Jamaica Plain

Info: 400 lilacs! Pack a picnic and tell your friends since this is the only day of the year that picnicking in the Arboretum landscape is allowed. Learn about the beautiful flowers with a guided tour or stroll on your own.

34) Boston Women’s Market Spring Makers Celebration at The Speedway 

When: Sun. 5/12

Where: Brighton

Info: Enjoy the outdoor courtyard at The Speedway with pizza, empanadas, snacks, and brews. And once you’re ready, have a blast checking out the many vendor booths, card making station, succulent popup, and build-your-own bouquet station.

35) Happy Hour Market at Boston Landing

When: Wed. 5/15

Where: Brighton

Info: Enjoy tunes while looking at the stalls from 10 local makers. Then, stay for extreme bingo for some fun and games – all while sippin’ and munchin’.

36) Coolidge @ The Speedway

When: Wed. 5/15

Where: Brighton

Info: One of our fave local theaters is partnering with the Charles River Speedway for movie nights once a month. The monthly May feature is ‘Bring It On,’ so take a seat, grab a snack, and watch this iconic cheerleading movie.

37) Boston’s National Bike to Work Day Festival 2024

When: Fri. 5/17

Where: City Hall Square

Info: May is National Bike Month. Take a ride with a neighborhood-based group ride and end with complimentary breakfast snacks and coffee in Downtown. You can head to work after (or not) – we won’t tell!

38) Spring Block Party at Boston Landing 

When: Sat. 5/18

Where: Brighton

Info: Food, drinks, and a makers’ mart – oh yes! There will be free ice cream, face painting, glitter tattoos, and fun games too. Soak up the sun at this can’t miss event.

39) MOS Asian American & Pacific Islander Heritage Month Celebration

When: Sat. 5/18

Where: West End

Info: Head to the Museum of Science with friends and family for this weekend event that uplifts the voices of AAPI scientists and engineers. With your ticket purchase, you'll get access to panels, activities, and more. Plus, free giant-screen films will be playing in the Mugar Omni Theater, so show up early to get a ticket!

40) Franklin Park Kite & Bike Festival 2024

When: Sat. 5/18

Where: Roxbury

Info: Celebrate the 50th anniversary of this festival that marks the opening day at Franklin Park. Make, purchase, or bring your own kite. Enjoy food trucks and the outdoors. Kids can try out bikes and there will be free helmets given out. 

41) Dunkin’ Spiked Day of the DJ

When: Sat. 5/18

Where: Seaport

Info: Food trucks, Dunkin’ Spiked Tea and Coffee, and eight DJ sets – show your Dunks pride and party it up to kick off your summer.

42) New England Hong Kong Festival

When: Sat. 5/18

Where: Union Square

Info: A mini Hong Kong has come to our corner of New England. Enjoy Cantonese pop bands, lion dances, Cantonese opera performances, crafts, and small business stalls. You’ll learn about Hong Kong culture in the heart of Somerville.

43) Greater Roxbury Book Fair

When: Sat. 5/18

Where: Roxbury

Info: Books, books, and more books. Stop by and listen to panels with authors, meet local authors, peruse some book offerings, and more at this festival that celebrates the love for reading!

44) Boston Harbor Islands Free Ferry Weekend

When: Sat. 5/18 - Sun. 5/19

Where: Long Wharf

Info: This is one of my favorite Boston traditions and a great way to see the city in a new light. Get in line early to grab a ticket with friends, bring a picnic, and discover the Harbor Islands to enjoy the breeze, fresh air, and a respite away from the hustle and bustle. This year, you’ll get to visit the fort at Georges Island.

45) Boston Night Market 2024

When: Sat. 5/18 - Sun. 5/19

Where: Downtown

Info: Enjoy a traditional, electric evening vibe on Saturday or a brunch theme on Sunday. No matter what you choose, there will be good food, vibrant artistry, and lively performances. 

46) 8th Annual Revere Kite Festival

When: Sun. 5/19

Where: Revere

Info: Say hello to the beginning of beach season with this family-friendly event. Build kites, decorate kites, fly kites, and watch professional kite flyers too. There will be live music and lots of activities to enjoy outside. Stop by and watch the blue sky become sprinkled with kites.

47) The Esplanade Community Day

When: Sun. 5/19

Where: Charles River Esplanade

Info: Cheer on folks running a 5k, enjoy free ice cream and Jamaican food, and listen to a Hatch Shell concert. There will be lots of family-fun activities for all ages, so grab a seat on the grass and stay a while to enjoy the scenes of the Charles.

48) Polish Fest Boston 2024

When: Sun. 5/19

Where: Dorchester

Info: Learn about Polish culture and its many traditions, and meet Polish-American Bostonians in our community. Enjoy food, dance performances, and live music by a polka band!

49) Inman Eats & Crafts 2024

When: Sun. 5/19

Where: Inman Square

Info: Take in the quaint vibes of Inman on a beautiful day while supporting local businesses. There will be a beer garden, local band music, goods and art from local makers, and tasty food from the best restaurants in town.

50) Vino + Vintage Market at Boston Landing 

When: Wed. 5/22

Where: Brighton

Info: Complimentary charcuterie and cheese boards, a free wine tasting, live music, and an art market? Yes, Boston Landing does it all. Shop at this favorite monthly market for a guaranteed good time.

51) Solve at MIT

When: Wed. 5/22

Where: Kendall Square

Info: Get inspired by the work of current innovators who are solving problems around the world. Listen to these panel discussions and meet leaders across a variety of industries to see how people are changing the landscape.

52) Field Trip: Plant Night with Emerald City Plant Shop

When: Wed. 5/22

Where: Allston

Info: Become a plant doctor at this free event where you’ll learn how to show some extra TLC to all your plant babies. There will be workshops on how to repot, propagate, and more!

53) Garden of the Flags on the Common

When: Thurs. 5/23 - Mon. 5/27

Where: Boston Common

Info: Honor the fallen and pay tribute to Mass. service members at the Soldiers and Sailors Monument. There will be over 37,000 flags planted on the green.

54) 2024 Boston AAPI Comedy Festival

When: Thurs. 5/24 - Fri. 5/25

Where: Roslindale

Info: Get ready for a whole ton of laughs. This festival gives a platform for Asian American and Pacific Islander performers to share their stories. Enjoy local talent at plenty of stand-up and improv sets.

55) Boston Calling Music Festival 2024

When: Fri. 5/25 - Sun. 5/26

Where: Allston

Info: For the food and concert lovers, grab a ticket for one day or all three. Take in the sounds of Ed Sheeran, Hozier, the Killers, and more. This music festival is well-loved, Boston teat.

56) MFA Memorial Day Open House

When: Mon. 5/27

Where: Fenway

Info: It’s one of the few times of the year that MFA offers free admission and you can see the stunning ‘Hallyu! The Korean Wave’ exhibition too. Make neon art, enjoy a photo booth, watch a taekwondo demonstration, and more!

57) Harvard Art Museums at Night

When: Thurs. 5/30

Where: Harvard Square

Info: See the Harvard Art Museums at night where there will be live music, light bites, and drinks. Get lost in over 3 floors of galleries and make some art too.

58) Patio Season

Info: Dine al fresco at some of the most unique and beautiful patios in Boston. Whether it’s interesting locations, spectacular views, or unforgettable ambiances, you’ll have a great time trying out great food and drink at one of these places.

59) Beer Garden Season

Info: Enjoy the outdoors with a brew in hand with this roundup of all the beer gardens you have to check out in the city. May is the perfect time to start your beer garden adventure for the spring/summer season!

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05/01/2024 09:00:00 05/31/2024 23:00:00 America/New_York Everything Fun to do Around Boston in May 2024 <p>May is the month when the city comes back to life after a chilly slumber. Flowers are blooming, the warm weather is lingering, and more people are out and about. Take advantage of this beautiful... Boston, Boston, MA false MM/DD/YYYY

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