Top Boston Dog-Friendly Trails and Hikes to Explore

There are so many great walking trails and hikes to go on around the Greater Boston, MA, area. If you’re searching for a new spot to explore with your pup, maybe switch things up and take in different city views, we’ve got the list for you.

Scenic stroll for those easy walking days:

  1. Charles River Esplanade – Boston, a 3 mile stretch along the beautiful Charles river with plenty of greenery, playgrounds, and iconic city views (get the cameras ready!).
  2. Arnold Arboretum of Harvard University – Boston, in the Jamaica Plain and Roslindale neighborhoods, gorgeous 281-acre preserve with both grass and paved roads (kid-friendly and easy for strollers!).
  3. Jamaica Plain Pond – Boston, in the Jamaica Plain neighborhood, 1.5 mile pathway loop around a freshwater pond that used to be a glacier basin.
  4. Stodder’s Neck – Hingham, offers an off-leash dog park area, and harborside walking trails.
  5. World’s End – Hingham, 251 acres of coastline, fields, and pathways. Make sure to give yourself some time to take in the views.
  6. Commonwealth Ave – Boston, located in Back Bay, it’s a greenway with statues and memorials that stretch from The Fens to the Boston Public Gardens. It’s one of our favorite walks to see seasons change as the trees reflect it and the beautiful homes along the walkway decorate for every holiday.
  7. Castle Island – Boston, 3 mile stretch with water views, a 22-acre park, and iconic New England eats. It is full of history too. You can visit Fort Independence used during colonial times up until WWII. And grab delicious foods from Sullivan’s, known for their ice cream, hot dogs, and seafood –think fried shrimp, lobster rolls, the whole nine.

Actual hikes for when you’re up for an adventure:

  1. Middlesex Fells Reservation – state park that covers 2,200 acres, with a dedicated off-leash dog park area, you can hike, fish (check out Spot Pond), and explore for hours.
  2. Blue Hill’s Reservation – 7,000-acre state park close to Boston has rugged rocky trail options along with easy trails. In fact, they have 125 miles of trails to try out.
  3. Walden Pond Reservation – 1.7mile loop around the pond is a charming reminder of the nature that Henry David Thoreau wrote about. You can still see his simple cabin (replica) on the shores.