Spring is in full swing and Boston is coming alive once again. From flower festivals to tea parties and everything in between, here are the top events, activities, and things to do in Boston this month.
1. Enjoy a performance of classical music under candlelight
Calm your mind and experience classical music in a whole new light with these sensational concerts located in historical Boston venues. Throughout May, the Candlelight Concert series will feature a wide variety of themed repertoires. Get tickets here!
2. Check out this incredible Flamenco show in the area for a limited time
Memorial Day weekend, on May 23 and 24, the award-winning Flamenco dancer Patricia Donn, and a group of talented dancers, percussionists, singers, and guitarists will take the stage at Arlington’s historic Regent Theatre. Learn more and reserve seats to the fiery show here!
3. Sail around the Boston Harbor for a day of sightseeing
Cruise aboard the beautiful Adirondack III, a 80-foot pilot schooner of the 1890s on this 90-120 ride through the beautiful Boston Harbor. You’ll sail past Seaport, Castle Island, Fort Independence, Spectacle Island, and Long Island Head Light. The knowledgeable captain and crew will show you Boston like you’ve never seen it before on this family-friendly ride filled with history and beauty!
Meet your captain at the Classic Harbor Line Boston behind the Boston Harbor Hotel
4. Celebrate mom with a festive brunch
May 11 is Mother’s Day! Take mom out for a classic Mother’s Day brunch or get matching bracelets zapped to your wrists as a symbol of unconditional love!
5. …or take mom for a spin in a private helicopter
Helicopter Tour Boston is an awesome treat to show mom just how much she means to you! The private rides fit two passengers, and have a photographer on board, so you and mom can capture the memories while staying present in the moment! You can fly over the city, take a sunset ride, a night tour, or for the Cape fans check out the sea from above!
Find it at 125 Access Rd, Norwood MA
Norwood Memorial Airport
6. …and treat her to a proprietary laser facial in Back Bay
If your mom is a self-care junkie or tech fanatic, she’ll love the proprietary laser facials at Skin Laundry. Bridging the gap between consumers and professional-grade medical lasers, Skin Laundry offers quick 15-minute facials that pause the clock and give an instant glow. Treat her to one facial or enroll her in “Laundry Club” for some regular pampering.
7. Go on a self-guided foodie adventure with clues and mystery picnics
Enjoy the lovely springtime weather and go on an adventurous culinary experience! This mystery picnic date includes solving puzzles and riddles sent to your smartphone to figure out the location of your stunning secret picnic spot. You can go on this 3-hour picnic extravaganza celebrating your mother or with a group of friends—it’s up to you!
8. Take an educational (and delicious) pizza tour in the North End
Whether you’re looking to entertain out-of-towners or want to learn some pizza history yourself, you can enjoy a pizza-powered guided tour around Boston’s historical North End. On the tour, you’ll visit five history-laden Freedom Trail sites and snack on pizza as you go along. Get your tickets to the experience here.
9. Work out in Seaport at Boston’s largest free outdoor workout series
Looking to get in shape this summer? We have the perfect activities for you! Seaport is bringing back their free outdoor workout series, Seaport Sweat, from May 5 through September 30 this year. Back for its eighth season, the community-driven series offers nearly 200 fitness classes.
10. Sun and slurp on Boston’s only floating oyster bar
On a sunny day, have an adventure in East Boston. The 245-foot floating “Tall Ship” is one of the best places in the city for a waterfront meal and making new friends.
11. Explore Boston’s 21-stop innovation trail
Candy factories. The instant camera. Getting Apollo spacecraft to the moon. The first surgery under anesthesia. The Innovation Trail shows a myriad of discoveries and advancements from a diverse group of men and women, how gaining our independence as a nation after the Revolution was just the beginning. What happened in Boston after America became an independent nation is equally as astounding and this 21-stop trail from Downtown to Cambridge shows it all.
12. Play outdoor pickleball at this rooftop in Kendall Square
The newly installed pickleball courts at Kendall Square’s rooftop urban oasis are a must this spring and summer! The space also doubles as a volleyball court and boasts plenty of green space for free yoga classes, outdoor cookouts, and even dance classes!
13. Attend Lilac Sunday at the Arnold Arboretum
Harvard’s beloved Arnold Arboretum has a beautiful selection of trees year-round, but it’s most popular in early May when the lilacs bloom near the path on Bussey Hill. Their annual Lilac Sunday always falls on Mother’s Day (which is May 11 this year), and it’s a gorgeous display of springtime blooms.
14. Explore the hidden gardens of Beacon Hill
Boston’s Beacon Hill neighborhood hosts a tour once a year of the houses’ gardens, and the Hidden Gardens tour is set to return this year on May 15. Whether rain or shine, you’ll have access to see the fabulous private gardens of the Beacon Hill Garden Club, and they’re certainly a sight to behold. Get your tickets and more information about the event at their website.
15. Gallup through fields of Lavender in Holden
To celebrate one of the prettiest times of the year, The Farm at Summitwynds blooms into a Lavendar Haze, with over 4,000 lavender plants in the ground. Walk through fields of lavender all through the summer, try lavender honey, check out the show horses, and snap photos at the retro lilac photo booth.
16. Visit a magical rose garden
The Kelleher Rose Garden reopens in May for the season, and it will only get more beautiful as the season progresses! The garden contains more than ten classes and 200 varieties of roses. In total, the garden has almost 1,500 plants! It’s completely free to visit and it’s open to the public from 7am to 5pm daily, May through October.
17. Try out a new restaurant
New spots have been popping up left and right in the city this spring! For your next night out in May, try something new and venture out of your comfort zone by checking out a new business. Our favorite new spots open this spring are:
18. Dine at a rooftop restaurant
It’s officially rooftop season in Boston again. From Lookout’s stunning views of the Seaport to Felipe’s Taquería’s cozy rooftop with twinkling lights and scrumptious tacos, these awesome Boston rooftops have it all! Enjoy the warmer weather and check out our favorite rooftops in the city.
19. Kickoff summer with a trip to one of these local beach towns
Two Massachusetts beach towns were named among the “best small coastal towns in America.” Take a trip for Memorial Day or plan a few throughout the month!
20. Toast with oolong and scones at the Public Library’s secret tearoom
Whether for Mother’s Day or just a treat, the Boston Public Library Tea is a quintessential experience. The elegantly refined tea towers with yummy treats and fragrant sips.
21. Cheer on the Sox at Fenway Park
It’s Sox season and if you’re out of things to do, a Red Sox game never fails! After, grab dinner and make sure to check out this late-night donut spot in Fenway serving up fried deliciousness until 2 AM.
22. Take a round-trip train to Portland, Maine with a BOGO deal
Bostonians can take the Downeaster to Portland and split the fare with a friend for a BOGO round-trip deal. Treat yourself to one of the best lobster rolls in the world while you’re there!
23. Hang around a private treehouse in Vermont
Winvian Farm offers a lovely hideaway just under 3-hours from the city. You can have your very own treehouse and live in it too! Check out our full list of abstract retreats in and around the city for the perfect Memorial Day Weekend.
24. Support the Bakes for Breast Cancer movement
Bakes for Breast Cancer Massachusetts returns for its 26th year from May 9-15, helping to raise funds and awareness for breast cancer research. “We are on a mission to end breast cancer for good, one sweet treat at a time,” said Bakes for Breast Cancer Founder Carol Sneider. “The Massachusetts culinary scene is thriving, and in addition to our trusted partners that have participated year after year, we had more new venues reach out to us than in years past.
Participating Boston restaurants include Tatte, Rowes Wharf Sea Grille and more. Find the full list of Massachusetts participants online.
25. Celebrate Cinco de Mayo in style
May 5, Cinco de Mayo, celebrates the Mexican victory over the French in the 1862 Battle of Puebla. It is not Mexican Independence Day, which is actually September 16. However, festivities hold strong on May 5 across the globe. Here are a few spots to celebrate in Boston:
- Check out the Cinco de Mayo festival in Downtown Crossing on Monday, May 5 from 12-2 PM
26. Visit the massive Daffodil & Tulip festival in the Berkshires
Open now through mid-May, Naumkeag’s fifth annual Daffodil & Tulip Festival lets you wander through 8 acres of springtime flowers in full bloom. Decorated with over 75,000 daffodils and tulips, you’ll be able to tiptoe through the garden and the first floor of the house, which has a seasonal gift shop inside right now. Read more about it here.
27. Enjoy live music for free at Somerville’s Porchfest
Porchfest returns on May 10 from 12-6 PM! Many streets in Somerville will transform into stages, with roads shut down and nothing but live music and good vibes. Performers to get excited about include Friend of a Friend, the duo of Claire Molek and Jason Savsani. They just produced their third studio album with M83’s Jordan Lawler and will bring incredible sound during Porchfest on May 10!
28. Taste your way through bites from 30+ of Boston’s top chefs at this charity showcase
Taste of the Food Bank returns on Thursday, May 8 with a lineup of over 30 critically acclaimed chefs and purveyors! Notable participants such as Jody Adams and Steve Joanne Chang will cook up something special at this event aimed to help fight hunger and hosted by the Greater Boston Food Bank.
According to GBFB’s latest statewide study conducted in partnership with Mass General Brigham, 1.9 million adults in Massachusetts identify as food insecure, which means 1 in 3 Massachusetts adults do not know where their next meal will come from. Join the fight to end hunger and buy tickets for Taste of the Food Bank here!
29. Shop fresh and local at this waterfront farmers market
The HYM Investment Group and the City of Revere are launching a Spring Pop-Up Market series at The Yard @ Beachmont Square, bringing together local farmers, small businesses, food trucks, and interactive activities to celebrate the season. The May market takes place on May 17 from 11 AM-2 PM in partnership with the Revere Beach Farmers Market. There will also be food trucks, giveaways and more!
30. Join Project Bread’s 57th Walk for Hunger
The annual event returns on Sunday, May 4 to the Boston Common. The one-day event is set for Sunday, May 4 on the Boston Common, and will feature family-friendly activities, food and entertainment along the 3-mile loop. In its 57th year, Project Bread invites you to help raise more than $1 million to support the leading statewide food security organization’s approach to ensure food access for all children and families in Massachusetts. Register, learn more and donate here. Registration is free but donations and fundraising are encouraged!