May blooms bright and full of light! Experience America250, including the oldest homes in Sudbury, at the Sudbury Witness House Tour 5/2 and townwide celebration at Sudbury 250 Day 5/16. Join Framingham History Center for their annual house tour 5/17. Celebrate culture with the vibrant Holi Festival in Natick 5/16 and CultureFest in Ashland on 5/30. Enjoy music with Herman’s Hermits at TCAN 5/30 or Sunday Jazz Jam at Hopkinton Center for the Arts 5/10. 


The FIFA World Cup 26™ is coming to MetroWest Boston and you’re officially invited! Cheer on your favorite teams at our MetroWest Regional Fan Zones in Marlborough and Franklin, featuring giant jumbotron watch parties, food trucks, beer gardens, arts & crafts vendors, and family-friendly activities. Learn more at metrowestvisitors.org/world-cup!



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Photo: Cider Hill Farm

Welcome spring at Cider Hill Farm’s Tulip Fest, May 2–3 and May 9- 10, featuring free live music, self-guided blooming orchard walks, outdoor hard cider bars, food trucks, fitness and family activities and pick-your-tulips (event dates are subject to change per weather and crop availability). Join the Greater Cape Ann Chamber of Commerce for the return of Motif No. 1 Day. This celebration of Rockport’s iconic fishing shack on May 16 (rain date May 17) is an all-day family -friendly event in coastal Rockport.

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May is music month throughout Plymouth County! On May 2 & 3,  enjoy “Music For All” at Choral Art Society in Scituate and “Blockbuster Broadway” at the Philharmonic Orchestra in Plymouth. May 8 & 9 brings "ABBAMANIA" to Company Theatre in Norwell, while May 9 & 10 brings “Music to Lighten the Darkness” at Plymouth’s Pilgrim Festival Chorus and “Happy Together” to Duxbury’s Snug Harbor Community Chorus. The Hingham Rasa String Quartet presents “Counterpoint in Bloom” at South Shore Conservatory on May 16. Plus, Plymouth’s Spire Center and Memorial Hall offer weekend concerts and a variety of performers. Visit https://seeplymouth.com/events/month/2026-05 for all May musical performances!


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Southeastern MA

May blooms with creativity in Bristol County as Artweek SouthCoast launches May with open studios, dynamic performances, inspiring exhibitions, and hands-on experiences for all ages. Spring festivals, farmers markets, live music, family fun, and seaside escapes energize Southeastern Massachusetts. Celebrate local artists, fresh flavors, coastal communities, and sunny days, then plan your May getaway at Southeastern Mass Visitors Bureau. Culture, creativity, and coastal charm shine all month long with unforgettable seasonal moments for everyone.


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ArtWeek Berkshires is an annual celebration of local creativity! This year, ArtWeek will be held May 15-25. Come enjoy 100+ hands-on or behind-the-scenes events and open studios across the region. Experience gallery shows, live performances, poetry readings, painting demos, and so much more! You can find all the events here. Spring is the perfect time for a Berkshires getaway with family and friends - come for the art, and stay to experience all that Berkshire hospitality has to offer. Enjoy farm-to-table dinners, comfortable accommodations, historic homes and museums, and plentiful outdoor activities. Check out Berkshires.org to find all that you need to curate your perfect Berkshires adventure! 


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Doors Open Lowell on Saturday, May 9 offers an insider's look into many of Lowell’s magnificent historic buildings! Being presented for the 21st time, Doors Open Lowell is a free annual event held during National Preservation Month, celebrating Lowell’s architectural heritage, urban living, and culture that makes the community a creative and exciting place to live, work, and visit. This year is particularly exciting as Lowell is celebrating the Bicentennial of its founding throughout 2026 so be sure to visit one of our new sites this year, the Stone House, site of Lowell’s first town meeting in March 1826.

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Photo: Glass in Flight at New England Botanic Garden

May in Central Massachusetts brings a lively mix of arts, comedy, festivals, and family celebrations. Catch the National Baseball Poetry Festival blending America’s pastime with spoken word at Polar Park, high-energy thrills come to DCU Center for Monster Jam, and see standout comedy from Gina Brillon and Mike Goodwin. Celebrate spring with a Mother’s Day Lavender Tea at a farm or brunch in a barn, and explore Glass in Flight at New England Botanic Garden.



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Experience the buzz at the Annual Greenfield Bee Fest, honoring Lorenzo Langstroth, the "Father of Modern Beekeeping," on Saturday, May 16! Dive into a hive of activities from 9 am to 4 pm, celebrating the vital role of honeybees in our ecosystem. Paint hives, join the Pollinator's Parade, enjoy food trucks and farmers’ markets, and indulge in bee games. Explore crafts, lectures, and music that highlight the importance of bees. Plus, don't miss the Bee Space garden awards and beekeeping insights. Learn, play, and preserve our precious pollinators. Get more information here!

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Panda Fest returns to Boston May 15–17 at Ohiri Field at Harvard University for its second year! Following a sold-out debut, the fast-growing outdoor Asian food and culture festival expands with 80+ vendors, 200+ dishes, live performances, artisan markets, and hands-on cultural activities. Guests can explore cuisines from across Asia, enjoy traditional and contemporary entertainment, and experience fan-favorite panda-themed attractions, interactive games, and photo-worthy installations throughout the festival grounds.


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The 2026 Cape Cod Travel Guide magazine is packed with insider tips on where to stay, play, and dine on Cape Cod. Browse the latest edition and start dreaming of your next visit!Enjoy engaging feature stories on unforgettable kayak adventures, the best waterfront escapes, farm-to-table dining, gallery hopping, luxe shopping, must-see stops along the Cape Cod Rail Trail, shoulder-season weddings, and a seasonal fishing guide. Stunning photos, maps and a comprehensive events calendar are also inside! Discover the one-of-a-kind experiences that make Cape Cod truly magical and truly yours. Order a print copy or find a digital version here.

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May is a vibrant month for live events across Western Mass. Leading the way is Springfield Symphony Hall with Brahms & A Modern Voice, presented by the Springfield Symphony Orchestra on May 2. On May 23, Cinderella's Tom Keifer performs with special guest Buckcherry. The month closes out with Theresa Caputo on May 29 and comedian Brad Williams and J.B. Ball on the Tall Tales Tour on May 30.

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Photo: Paradise City Arts Festival, Lynne Graves

March into May under a rainbow at Hampshire Pride, the area’s most popular LGBTQ+ celebration. Explore children’s literature at the Mass Kids Lit Fest, and discover kid-created goods at the Kids’ Makers Market. When the weather turns warm, book a riverboat tour on The Lady Bea, and as the month wraps up, don’t miss outdoor dining and concerts at Summer on Strong and the 3-day arts-and-music showcase that is the Paradise City Arts Festival!



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From Renaissance Faires and apple blossom festivals to live music, comedy nights and Memorial Day ceremonies, May is one of the region's most vibrant months. Get outside for forest bathing, guided garden tours, and farmers markets, or explore your creative side with art workshops, painting classes, and botanical craft events. Families will find no shortage of fun, with nature play days and open play events running all month long!


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Photo: Michael Blanchard

As May on the Vineyard unfurls, get out and participate in the fun and events: Bike MS Ride the Vineyard (5/2); MS Kentucky Derby at HV (5/2); Mother’s Day on MV (5/10); Edgartown Porchfest (5/16); Martha’s Party Wedding & Event Conference (5/18); MV Environmental FilmFestival (5/21-24); Vineyard Artisans Memorial Day Festival (5/23-34); MV Garden Club Annual Plant Sale (5/23-24); Hospice MV Memorial Road Race (5/24). Stay, golf, dine, shop, hike, bike, kayak, SUP, fish, surf! Endless action and oodles of fun! 

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Plan a Summer/Fall trip to MASS MoCA in North Adams for major exhibitions and performing arts. See Michael E. Smith, the group show Spatial Poems, and Amanda Lovelee’s outdoor Homecoming. Look ahead to commissions by Daniela Rivera and Laurent Grasso, and get lost in Grasso’s Metaphysical Maze in Building 5. With galleries, music, and events across campus, it’s a must-visit destination.


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Nantucket in May is seriously more sumptuous than April! Abundant blooming flowers and foliage festoon the island. Take a Full-Moon Nature Walk May 1, 8:30 to 9:30 pm; Nanpuppets at Something Natural (5/2); Live Music at Cisco Brewers: Cosmic Jibaros – Nantucket Events (5/2); Historic Bike Tour – Nantucket Events (5/2); Nantucket Skating Club Spring Show (5/2); Free birding field trip (5/6); Figawi (5/22-25); New Moon Film Festival (5/23); Nantucket Food & Wine Festival (5/27-31). Take in all the fun then stay, dine, shop and explore!

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