A few weeks back we spent a weekend getting to know the pet friendly aspects of Boston. What a great place to hang out with your dogs! A bright patchwork of 21 neighborhoods, the city celebrates its dynamic history and its marriage to the water. The Charles River not only gives Boston access to the Atlantic, but also ensures the city remains compact and walkable. Entertaining the dogs for a couple of days was no problem – in fact, we didn’t get to see it all!

The Freedom Trail

We started with The Freedom Trail, a 2.5 mile red brick trail through the city that leads you past 16 Colonial and Revolutionary historical sites like Boston Common, Paul Revere’s house, the Old North Church and Faneuil Hall. We thought it would be a good way to get an overview of downtown while checking an item off our bucket list … apparently, hundreds of other tourists felt the same way. My suggestion for those of you touring with dogs: go on a weekday – or at least walk on the opposite side of the street from the red brick path to avoid the hoards.

Boston Common - Boston, MA

Ty and Buster at Boston Common - Boston, MA

Faneuil Hall - Boston, MA

 Rose Kennedy Greenway

Getting off the trail and jumping on the Rose Kennedy Greenway was much more relaxing. This series of parks and green spaces stretches for about 1.5 miles from New Sudbury Street to Summer Street. With plenty of space to maneuver and things to sniff, we were all relieved to find this oasis in the city.

Ty and Buster - Boston, MA

Rose Kennedy Greenway - Boston, MA

Harbor Walk

From the end of the greenway it was only steps to the Harbor Walk, a public walkway that runs along the harbor for 38 miles. Winding by parks, public art installations, and seating areas, it’s the perfect space to soak up the ambiance of the waterfront.

Harbor Walk - Boston, MA

Beacon Hill

Of course, no trip to Boston would be complete without a stroll around the Beacon Hill neighborhood. Just off Boston Common, this residential area is named for the beacon that once stood here at the highest point in central Boston. Now folks come to admire the distinguished row homes, narrow brick streets, and working gas lamps. It’s like stepping back in time.

Ty and Buster on Beacon Hill - Boston, MA

Not far from Beacon Hill is the Boston Bruins hockey arena where Ty posed with this statue of Bobby Orr, commemorating one of hockey’s most famous goals scored in 1970, giving Boston their first Stanley Cup since 1941. Ty looks thoroughly impressed, don’t you think?

Ty with Bobby Orr - Boston, MA

Charles River Esplanade

You could easily spend a whole day basking in the Esplanade. This park, on the banks of the Charles River, is like the city’s back yard. Sun bathers, kayakers, runners, bench warmers, and lots and lots of dogs come here to savor the scenery and sprawl in the grass.

Charles River Esplanade - Boston, MA

Ty and Buster on the Charles River Esplanade - Boston, MA

Charles River Esplanade - Boston, MA

Where to Stay

There is a great selection of pet friendly hotels in Boston, but your options don’t end there! We learned that pets are welcome on the “T” – Boston’s public transit train system – during off-peak hours as long as they are leashed or crated and do not annoy fellow passengers or sit on the seats. There are a bunch of train lines, so it’s simple to breeze into the city from places like Providence, Worcester, Plymouth, and Rockport.

Next Time

We didn’t make it down to the Back Bay neighborhood. I pictured us strolling down Newbury street, window shopping or people watching from the patio of a coffee shop, but it didn’t happen on this trip. That just gives us a reason to go back!


We finally made it back to Boston. Read our most recent paws-on-the-ground research now!

Massachusetts' Top Pet Friendly Attraction: Boston's Freedom Trail | GoPetFriendly.com

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  • do you remember where you parked when you went to Boston? I am doing a dog friendly even there on Saturday and it is near Storrow Drive and on the Esplanade. I hear there are low underpasses on Storrow and not sure if the Back Bay is RV friendly. Any suggestions?