May 2026 in New England: Top Events and Travel Deals

Of 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.

Yankee Out & About in May

There are so many benefits to expressing yourself in a handwritten letter: gaining clarity, strengthening relationships, boosting happiness for you and the receiver… and maybe even touching the future. So break away from screens, and spend a spring weekend on Cape Cod with me at the spectacular Ocean Edge Resort. From May 15-17, I’ll be leading a Write Place, Write Time wellness retreat that combines writing time with calming, creativity-boosting experiences, including a floating sound bath!

Can’t make it to the Cape? On Saturday, May 2, at 11 a.m., the Housatonic Valley Association has invited me to host a free outdoor writing session, Walk, Breathe, Write, at Topsmead State Forest in Litchfield, Connecticut, and YOU are invited to spend a phone-free hour getting back to nature, movement, and making words with a pencil or pen. Please register online in advance.

New in New England in May 2026

iREV Mixed Reality Tour | Lexington, MA

Past and present collide in Lexington thanks to the debut this month of a new tour that combines human guides dressed in colonial garb and virtual reality headsets that allow participants ages 10 and up to venture inside a historic building that no longer stands on the Lexington Green. From May through October, the 20-minute iREV Mixed Reality Tour is available Saturdays and Sundays at noon and 12:30 p.m. (arrive at least 10 minutes early). Tickets, which can be reserved online, are $25 for adults, $22 for students ages 10-17.

Hidden Gems from the Guitar Museum of New England | West Concord, MA

The Guitar Museum of New England doesn’t quite exist yet, but as part of the month-long, event-packed Hidden Treasures Festival of Nature, Culture & History in the Freedom’s Way Heritage Area this May, you’ll have four opportunities for a sneak preview of what’s destined to become the first and only guitar-devoted museum in the Americas. Programs on May 2, 9, 16, and 23 in a pop-up museum space will feature performances or a chat with the curator. Admission is free.

Weekend of May 2-3, 2026

Seasonal Harvest Dinner at Love Farms | Dennis, MA

Get a jump on the first weekend of May by heading to Cape Cod the evening of Friday, May 1, for a memorable dinner at the new Love Farms, featuring all of spring’s freshest bounty. The Harvest Dinner experience, priced at $180 per person, can be enhanced with wine pairings for an additional $50 per person. And trust us, you won’t want to leave without some treats from the Love Farms market, including some of the nicest logo merch we’ve seen.

Connecticut Clay Crawl | Statewide, CT

For the first time, members of the Connecticut Clay Guild are collaborating to invite the public into their studios for an inspiring weekend of demos, conversations with artists, refreshments from local providers, and shopping for one-of-a-kind pieces. Be sure to pick up a passport at your first Connecticut Clay Crawl stop. Each visit is one entry to win a handcrafted prize, and if you manage to visit all 14 stops on the trail, you’ll earn 10 bonus entries. Studio hours are 10 a.m. to 4 p.m. each day, Saturday and Sunday, May 2 and 3.

Kentucky Derby Doings in New England

We may be far from Churchill Downs, but on Saturday, May 2, there are plenty of places to celebrate the 152nd Kentucky Derby here in New England including:

~ The Newbury Boston is the place to be for the Kentucky Derby “Darty” (that’s a Day Party!), a fundraiser for BINA Farm Center and its equine-assisted therapy programs. Highlights include live music, live Derby coverage on a big screen, Derby-inspired cocktails and hors d’oeuvres, and an invitation to wear your fanciest hat. Purchase $155 party tickets online.

~ The Vanderbilt in Newport, Rhode Island, which is hosting “A Day at the Races” activations including a live bluegrass band, Southern-inspired cuisine, a race lottery, cash bar, and the opportunity to dress your springtime best for photo ops in the newly restyled Vanderbilt Room. Tickets are $126 and can be reserved online in advance.

~ 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 a themed buffet, souvenir T-shirts and mint julep glasses, betting opportunities, and an appearance by horse racing personality Chantal Sutherland. Call 860-862-9172 for Reservations.

Tulip Mania at the Garden at Elm Bank | Wellesley, MA

The Massachusetts Horticultural Society’s annual Tulip Mania at the Garden at Elm Bank celebrates its final weekend, May 2 and 3, and you won’t want to miss all the vibrant photo ops. Timed tickets are required and include five precut or pick-your-own tulips to take home. Admis

Oysters at the Point | Old Saybrook, CT

Saybrook Point Resort and Marina is an oyster lover’s place to be on Sunday, May 3, from noon until 3 p.m. Their Oysters at the Point event features not just locally harvested bivalves but champagnes and cocktails, live music, and water views. All attendees must be 21, and $91.50 tickets can be purchased online.

Weekend of May 9-10, 2026

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, and all moms receive complimentary welcome gifts including two signature Bellini cocktails and cashmere sleeping socks made by New England-based luxury linen company Matouk. 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 (some offers require purchase of another admission ticket for an accompanying child or adult):

~ Heritage Museums & Gardens, Sandwich, MA
~ Billings Farm & Museum, Woodstock, VT
~ Charmingfare Farm, Candia, NH
~ Franklin Park Zoo/Stone Zoo, Boston/Stoneham, MA
~ Connecticut Trolley Museum, East Windsor, CT
~ Seashore Trolley Museum, Kennebunkport, ME

Weekend of May 16-17, 2026

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 17, at Lime Rock Park. Tours of private and public gardens in western Connecticut and eastern New York on Saturday, May 16, are also a highlight. Purchase tickets online in advance for this popular weekend’s events.

ArtWeek Berkshires | Various Locations, MA

The 11-day ArtWeek Berkshires celebration is in full swing starting this weekend: There are more than 100 events planned in the western region of Massachusetts between May 15 and 25. Visit galleries and artists’ studios, attend a demo or performance, and even try your hand at something new.

Brimfield Outdoor Antiques Show | Brimfield, MA

Join the treasure hunters at the first Brimfield Outdoor Antiques Show of 2026, which runs May 12-17. This enormous gathering of sellers and seekers has been a tradition since 1959.

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 21, and cosplay is, of course, encouraged.

Weekend of May 23-25, 2026

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.

Wildquack Duck Race & Music Festival | Jackson, NH

On Sunday, May 24, 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.

Spring Open Studio Weekend | Statewide, VT

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 23 and 24, each showcasing members of the Vermont Crafts Council and their handcrafted works.

Memorial Day Weekend Craft Festival | Meredith, NH

For the 34th year, juried artisans will gather for three days of showing off their latest creations at a Memorial Day Weekend Craft Festival, which runs May 23-25 at Mill Falls Marketplace in New Hampshire’s Lakes Region. It’s the perfect opportunity to tuck away thoughtful gifts you’ll be giving all year long.

Weekend of May 30-31, 2026

Greenwich Concours d’Elegance | Greenwich, CT

In Connecticut, an event with massive appeal for auto enthusiasts is on tap May 29-31, as the Greenwich Concours d’Elegance brings some of the world’s most celebrated cars together in one place.

The Witch Market | Barre, VT

Tarot Goddess Co. is hosting Witch Markets all over New England this spring and summer, and this final weekend in May finds their collection of vendors convening near Vermont’s capital at Barre City Recreation Services. Purchase your $10 admission ticket online in advance for Saturday or Sunday, May 30 or 31, from noon until 5 p.m., then dress your witchy best and enjoy an afternoon of spiritual readings and bodywork treatments, plus shopping for products for gardening, sustainable living, natural healing, and cooking up your own magic.

May’s Best Travel Deal

Gift Card Bonus from New England Inns & Resorts Association

Treat Mom (or yourself) to a getaway with a special offer from the New England Inns & Resorts Association. Purchase a $100 NEIRA gift card, valid at more than 350 of the organization’s member properties in the region, and you’ll receive an additional $20 gift card free with promo code LoveMom. Bonus cards must be used within a year of purchase. This offer applies to physical gift cards only and is available through May 15.

What are you excited to do this May in New England? Let us know in the comments below!

Kim Knox Beckius

Kim Knox Beckius is Yankee's travel & branded content editor. A longtime freelance writer/photographer and Yankee contributing editor based in Connecticut, she has explored every corner of the region while writing six books on travel in the Northeast and contributing updates to New England guidebooks published by Fodor's, Frommer's, and Michelin. For more than 20 years, Kim served as New England Travel Expert for TripSavvy (formerly About.com). She is a member of the Society of American Travel Writers (SATW) and is frequently called on by the media to discuss New England travel and events. She is likely the only person who has hugged both Art Garfunkel and a baby moose.

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