Things to Do in New England in June 2024

Do you remember the elation of the last day of school? Here in New England, June lobs up plenty of opportunities to feel the same child-like sense of exuberance, whether you’re enjoying simple pleasures like picking your own strawberries or biking Vermont’s Island Line Trail.

As I look at my calendar for June, I’m astounded by the choices I’ll need to make. How are there so many enticing events happening simultaneously? I’m going to drop a few that are tugging at me below to help you sort your own June weekends, and perhaps we’ll bump into each other as I’m traveling throughout New England this month. Yankee‘s annual Summer Travel Guide is bursting with even more of our editors’ picks for the best ways to spend your well-deserved summer leisure time including the rare five full weekends in June.

Weekend of June 1-2, 2024

Pride of Woodstock | Woodstock, VT

June is Pride Month, and the quintessential New England town of Woodstock, Vermont, is welcoming everyone to its first “Small Town, Big Love” Pride of Woodstock celebration featuring a “Made with Pride” Arts and Crafts Fair on the Woodstock Village Green, a High Heel Race, Drag Brunch at the Woodstock Inn, Tea Dances, and many other festivities.

Greenwich Concours d’Elegance | Greenwich, CT

In Connecticut, the first weekend of June has massive appeal for auto enthusiasts, as the Greenwich Concours d’Elegance brings some of the world’s most celebrated cars together in one place.

National Trails Day

If you love hiking, the American Hiking Society’s annual National Trails Day on June 1 features opportunities to spend time with fellow outdoor enthusiasts throughout the New England states.

Weekend of June 8-9, 2024

Wiscasset Wormfest | Wiscasset, ME

Some day, you will tell your grandchildren and great-grandchildren you were there for the first-ever Wiscasset Wormfest. The picturesque Midcoast Maine town is leaning into its distinction as the world’s worm-harvesting capital. Will this festival be quirky? Ayuh! Should you enter the Mud Pie Eating Contest? Of course.

Ultimate Provence Rosé Launch & Summer Clambake | Chatham, MA

Want to do something a bit more elevated? June 8 is National Rosé Day, and Chatham Bars Inn on Cape Cod will debut its new private label Ultimate Provence Rosé at a New England Clambake.

Connecticut Landmarks Juneteenth Festival | New London, CT

Juneteenth falls on Wednesday, June 19, in 2024, but one notable community celebration, a Juneteenth Festival hosted by Connecticut Landmarks and the City of New London, takes place on Saturday, June 8.

Weekend of June 15-16, 2024

Quechee Hot Air Balloon, Craft and Music Festival | Quechee, VT

The annual Quechee Hot Air Balloon, Craft, and Music Festival in Vermont will lift your spirits even if you don’t book a balloon ride. 

Free Father’s Day Fun

Celebrating Dad? He’ll be proud of your frugality if you take him to one of these New England attractions where dads are admitted free on Father’s Day:

Weekend of June 22-23, 2024

The Newport Flower Show | Newport, RI

The Newport Flower Show returns to its usual location, Rosecliff mansion, with a theme of “At Home” this year. With eye-popping floral displays both outside and inside the recently refurbished Gilded Age stunner, it’s guaranteed to be one of this summer’s most beautiful weekends.

Travelers Championship | Cromwell, CT

Hopefully, the sun will shine on the Travelers Championship, the largest PGA Tour event to swing through New England each year. I can tell you for certain: It’s much more fun to watch golf in person than it is on TV. Top players committed to this year’s tournament include Scottie Scheffler, Keegan Bradley, and Rory McIlroy.

Maine Whoopie Pie Festival | Dover-Foxcroft, ME

Bound for Maine this weekend? The sweetest day of the year in Maine is June 22, when the Maine Whoopie Pie Festival consumes the town of Dover-Foxcroft.

Harbor Glow at Windjammer Days | Boothbay Harbor, ME

The week-long Windjammer Days celebration in the Boothbay region kicks off with a lighted boat parade, Harbor Aglow, on Sunday, June 23. Be sure to pick up a copy of the July/August issue of Yankee with all of my tips for finding the Boothbay area’s hidden highlights.

Weekend of June 29-30, 2024

St. Peter’s Fiesta | Gloucester, MA

Gloucester, New England’s enduring fishing village, celebrates the patron saint of fishermen during the annual St. Peter’s Fiesta, featuring traditions that range from a greasy pole contest that’s a spectator’s delight to the blessing of the fleet.

June’s Best Travel Deals

Kennebunk, ME

~ Don’t be a procrastinator! You’ll save 20% on a stay at The Wanderer cottages in Kennebunk, Maine, when you book at least 14 days in advance.

Ogunquit, ME

~ Book the Grand Reopening Package at The Dunes on the Waterfront in Ogunquit, Maine, for stays through June 21, and you’ll not only beat the summer rush, you’ll save 25% off the best rate and receive a complimentary VIP amenity. 

Yankee Out & About in June

On June 4, tune into NBC Boston’s Hub Today to hear Yankee‘s Senior Food Editor Amy Traverso talk about all of the best things to squeeze into a summer weekend in Boston.

Have you heard about Gloucester’s new music venue, The Cut? I’m looking forward to checking it out when I attend a North of Boston Convention & Visitors Bureau event there on June 11.

Join us at the annual Best of New Hampshire celebration, hosted by our sister publication, New Hampshire Magazine, on June 20 at Flag Hill Distillery and Winery in Lee, New Hampshire. Tickets to this sampling extravaganza are on sale now.

Our Marketing Director and I are headed to the Berkshires on June 21 for the first Bestie Bus New England Getaway at Canyon Ranch, and we can’t wait to meet all of the women who are traveling by bus from NYC for this ultimate best friends’ escape. Phone a friend… you can still book your spot!

Love chocolate? Love wine? Then join me aboard Naugatuck Railroad’s Chocolate Decadence Tour in Connecticut on June 28. This collaboration with Fascia’s Chocolates and the Railroad Museum of New England is offered on select dates throughout the summer and fall.

What are you looking forward to doing this June in New England? Let us know in the comments below!