Things to Do in New England in May 2025
Plan your May weekends… with Yankee! Don’t miss these May 2025 events and happenings in New England, plus this month’s best travel deals.
By Kim Knox Beckius|Apr 29 2025|
The Maypole dance is a tradition at Robin Hood's Medieval Faire, which begins its springtime run this month.
Photo Credit: Robin Hood's Medieval FaireOf all the months, May has the heaviest lift when it comes to transforming the New England landscape. More color emerges each day on the path from barren to blossoming, and it’s a treat to anticipate buds bursting into leaves, seemingly overnight.
Nothing excites me more in May, though, than the release of Yankee‘s annual Travel Guide to New England. This year’s May/June issue is a keeper, filled with more travel ideas than you could possibly pack into one summer, even if you start this month. If you haven’t already made plans for Mother’s Day Weekend, Memorial Day Weekend, and the rest of May, I’ve got plenty of ideas.
Weekend of May 3-4, 2025
Kentucky Derby Doings in New England
We may be far from Churchill Downs, but on Saturday, May 3, there are plenty of places to celebrate the 151st Kentucky Derby here in New England including:
~ The Vanderbilt in Newport Rhode Island, which is hosting “Day at the Races” activations including a live bluegrass band, lawn games, a Kentucky Derby headpiece contest, a race lottery, cash bar, and food stations (book online).
~ Mohegan Sun FanDuel Sportsbook in Connecticut, where the race will be shown on a 140-foot video wall, the largest in the Northeast, and there’ll be prizes for best dressed and best Derby hat (reservations required: book online).
~ Revere Hotel in Boston, where a Derby on the Rooftop Watch Party in the Lantern Lounge features Woodford Reserve mint juleps, live Derby coverage on the big screen, and a hat contest with a fabulous grand prize: an overnight stay (purchase party tickets online).
Weekend of May 10-11, 2025
Mother’s Day Weekend in New England
Celebrate your mom or her finest creation… you! I can’t think of a more fitting place than The Beatrice in Providence, Rhode Island: The whole hotel’s a tribute to developer Joseph R. Paolino Jr.’s late mom, Beatrice Temkin, a lifelong Rhode Island resident, community leader, and philanthropist. Book a Mother’s Day weekend stay (call 401-443-2960), and all moms receive complimentary welcome gifts including Seacoast Sweets chocolates, BeeKind bath amenities, and a signature bellini cocktail. Make reservations, too, at Bellini Providence, the hotel’s Italian restaurant.
If Mom taught you frugality is a virtue, take her to one of these New England attractions where moms are admitted free on Mother’s Day:
~ Charmingfare Farm, Candia, NH
~ Coastal Maine Botanical Gardens, Boothbay, ME
~ Connecticut Science Center, Hartford, CT
~ Franklin Park Zoo / Stone Zoo, Boston / Stoneham, MA
Photo Credit : Stone Zoo
Weekend of May 17-18, 2025
ArtWeek Berkshires | various western Massachusetts locations
The 11-day ArtWeek Berkshires celebration is in full swing starting this weekend: There are more than 100 events planned between May 16 and 26. Visit galleries and artists’ studios, attend a demo or performance, and even try your hand at something new.
Trade Secrets | Lakeville, CT
It’s the garden event to beat all New England garden events! Trade Secrets famously attracts celebrities like Martha Stewart, and you’ll understand why as you shop for rare plants and garden antiques on Sunday, May 18, at Lime Rock Park. Tours of private and public gardens in western Connecticut and eastern New York on Saturday, May 17, are also a highlight. Purchase tickets online in advance for this popular weekend’s events.
Brimfield Outdoor Antiques Show | Brimfield, MA
Join the treasure hunters at the first Brimfield Outdoor Antiques Show of 2025, which runs May 13-18. This enormous gathering of sellers and seekers has been a tradition since 1959.
Weekend of May 24-26, 2025
It’s Memorial Day weekend, and in addition to remembering those who have made the ultimate sacrifice for our nation, New England greets the unofficial arrival of summer with too many events to count.
Spring Open Studio Weekend | Vermont statewide
It’s Spring Open Studio Weekend in Vermont: a fun excuse for a road trip. There are 15 local tour loops to choose from on May 24 and 25, each showcasing members of the Vermont Crafts Council and their handcrafted works.
Wildquack Duck Race & Music Festival | Jackson, NH
On Sunday, May 25, the annual Wildquack Duck Race & Music Festival in Jackson, New Hampshire, is a solid day of free fun. Plus, if you buy a duck, you might waddle away with a fabulous prize.
Robin Hood’s Medieval Faire | Harwinton, CT
Make merry at Robin Hood’s Medieval Faire in Harwinton, Connecticut, where the fun is “joust” getting started during this opening weekend. Festivities continue Saturdays and Sundays through June 22, and cosplay is, of course, encouraged.
May’s Best Travel Deals
Photo Credit : Great Wolf Lodge
~ It’s Gonna Be MAY! Great Wolf Lodge has teamed up with *NSYNC’s Joey Fatone and Lance Bass for a special promotion in honor of the 25th anniversary of the band’s iconic song, It’s Gonna Be Me. On May 1 only, families can save up to 51% off stays at Great Wolf Lodge properties (there are two here in New England) by using promo code BEMAY when they book online for stays during the annual Summer Camp-In celebration, May 24 through August 25.
Yankee Out & About in May
Join me at Canyon Ranch in the Berkshires May 1-4 for Besties Weekend. As I learned during last year’s Besties Weekend, Wellness is Better Together. I’m looking forward to meeting new friends and teaching a workshop, The Lost Art of Letter Writing, on Friday afternoon.
What are you excited to do this May in New England? Let us know in the comments below!
