Farms & Food

Staff Favorite Picnic Spots

We asked our Trustees staff to tell us their favorite picnic spots.

We asked our staff to tell us their favorite Trustees picnic spots. More than half of our reservations made their list so you really can’t go wrong wherever you go, but here are a few highlights from every part of the state. You’ll find some of your favorites along with perhaps some undiscovered gems!

Dry Hill, New Marlborough 

“After a bit of a workout, the warm rocks make for a great picnic spot and there is never anyone else there.” 

Notchview, Windsor 

“Beautiful view across the fields from either of the two shelters, which have their own picnic tables.” 

Bear Swamp, Ashfield 

“A picnic table overlooking a vista that stretches all the way to Mount Snow in Vermont.” 

William Cullen Bryant Homestead, Cummington 

“So peaceful and what a view!” 

Peaked Mountain, Monson 

“A hike makes the food so much better at the top, and I love beautiful views while eating lunch!” 

Brooks Woodland Preserve, Petersham

“It’s a really nice walk in the woods and there are multiple spots to stop along the river to have a picnic.” 

Doyle Community Park & Center, Leominster 

“Winding paths and secluded garden spaces.” 

Jacobs Hill, Royalston 

“A quick walk out to the overlook from the parking area—great spot to sit and eat lunch while gazing at the awesome views of Long Pond and Tully Mountain.” 

Cedariver, Millis 

“A mowed path loops completely around one of the most glorious oak trees in the Commonwealth. An excellent place to lay out a picnic blanket and enjoy the tranquility on the banks of the Charles River.” 

Farandnear, Shirley 

“The arboretum and pavilion are ideal for a picnic or for anyone looking for a beautiful space to share with one or many. The specimen trees and shrubs are unique and located in a manner that allows for personal discovery and contemplation.” 

The Old Manse, Concord
“Inviting and intimate—a great spot to sit with a book and absorb the literature and history in this powerful place.”
Greenwood Farm, Ipswich 

“Very peaceful and nice views of the marsh.” 

Halibut Point Reservation, Gloucester 

“Set up your picnic on a giant boulder and soak up the sun while watching the waves and the cormorants, feeling the ocean breezes, and taking in nature’s beauty all around you.” 

Old Town Hill, Newbury 

“Climb to the top of the hill and take in the wide view of the Great Marsh. Then hike down through the woods and look at the Great Marsh up close. The trails cover some of the most varied of the Trustees landscapes.”  

Minton Stable Community Garden, Jamaica Plain

“A great way to spend time with nature in an urban setting.” 

Governor Hutchinson’s Field, Milton

“A wide-open field with distant views of the Boston skyline.” 

Governor Oliver Ames Estate, Easton 

“Dog-friendly, with a pond and interesting landscape that is fun for children to run around.” 

Eleanor Cabot Bradley Estate, Canton 

“A quiet secret, this location has it all—parking, beautiful spots for a picnic, and numerous walking trails.” 

Westport Town Farm, Westport

“Nestled into a quiet farming community and offers a mowed path down to the Westport River. It’s also close to the beautiful south coast beaches—great for a day trip.” 

Armstrong-Kelley Park, Osterville

“Plenty of picnic tables, a shady green for playing games, woodland trails to explore, and ice cream just up the road!”

Wasque, Chappaquiddick Island

“Stunning views and incredibly peaceful.” 

Go back to the Special Places home page