Part 21 of our 25-part Southeast road trip series takes us to the Bay State — and Massachusetts is one of the most iconic and dog-friendly destinations in the entire country. From the wild dunes of Cape Cod and the Gilded Age charm of Martha's Vineyard to the vibrant neighborhoods of Boston, the cultural riches of the Berkshires, and the historic streets of Salem and Newburyport, Massachusetts offers an extraordinary range of dog-friendly experiences.
🐾 Why Massachusetts?
Massachusetts is a state that rewards the curious traveler at every turn. Boston is one of America's most walkable and historically rich cities, with a dog-loving culture and some of the best restaurants in the country. Cape Cod is the quintessential New England beach destination, with miles of dog-friendly National Seashore beaches. The Berkshires have become one of the most vibrant arts and culinary destinations in the Northeast.
🏨 Pet-Friendly Hotels & Stays
Kimpton Marlowe Hotel — Cambridge
Zero pet fees, steps from Harvard Square, the Charles River, and some of the best restaurants in the Boston area.
Blantyre — Lenox (Berkshires)
A magnificent Tudor-style country house hotel on 110 acres that welcomes pets in select accommodations.
The Chatham Bars Inn — Chatham (Cape Cod)
A grand historic resort on the Cape Cod National Seashore that welcomes pets with stunning ocean views.
The Newburyport Inn — Newburyport
A charming boutique inn on the North Shore that welcomes pets, steps from the Merrimack River waterfront.
🍽️ Pet-Friendly Restaurants & Cafés
Island Creek Oyster Bar — Boston
One of Boston's most celebrated seafood restaurants with a dog-friendly outdoor area.
The Red Inn — Provincetown (Cape Cod)
A beloved Provincetown restaurant with a stunning dog-friendly outdoor deck overlooking Cape Cod Bay.
Mezze Bistro + Bar — Williamstown (Berkshires)
A celebrated Berkshires restaurant with a beautiful dog-friendly outdoor area and farm-to-table cuisine.
🍺 Dog-Friendly Breweries
Trillium Brewing Company — Boston & Canton
One of the most acclaimed craft breweries in America with dog-friendly outdoor spaces at multiple locations.
Tree House Brewing Company — Charlton
One of the most celebrated craft breweries in the entire country with a stunning dog-friendly outdoor space on a beautiful farm.
Notch Brewing — Salem & Boston
A beloved Massachusetts craft brewery with dog-friendly outdoor spaces. Their Czech-style lagers are extraordinary.
🌲 Dog-Friendly Parks & Trails
Cape Cod National Seashore
Miles of dog-friendly beaches in designated areas and trails through pitch pine forest. The Province Lands dunes near Provincetown are particularly spectacular.
Mount Greylock State Reservation — Adams (Berkshires)
The highest point in Massachusetts with dog-friendly trails to the summit and stunning views of five states.
Plum Island / Parker River National Wildlife Refuge — Newburyport
A stunning barrier island refuge with dog-friendly beach access in designated areas.
Walden Pond State Reservation — Concord
The legendary pond where Thoreau lived and wrote, with dog-friendly trails around the pond and through Walden Woods.
🗺️ Suggested Road Trip Route
Start in Boston & Cambridge → north to the North Shore (Salem + Newburyport) → west to the Berkshires → east through the Pioneer Valley → south to Cape Cod. Massachusetts is large enough to warrant multiple dedicated road trips.
🐶 Pro Tips
- Cape Cod in July and August is extremely crowded — the shoulder seasons are dramatically more dog-friendly.
- Provincetown is one of the most dog-friendly towns in America year-round — dogs are welcome almost everywhere.
- Tree House Brewing sells out of their most popular beers quickly — arrive early.
- Boston's Freedom Trail is dog-friendly and one of the great urban walking experiences in America.
Have a favorite dog-friendly spot in Massachusetts we should add? Drop it in the comments!
🐾 This is Part 21 of 25 in our Southeast Dog-Friendly Road Trip Series.
← Part 20: Rhode Island | ↑ Back to the Series Hub | Part 22: Vermont →