Stroller-Friendly Hikes in Boston

1. Spectacle Island — Boston

There aren’t many places where you can take a boat to go on a hike, but Spectacle Island in the harbor is one of them. Bring the stroller to tackle the 1.5-mile perimeter trail, where you’ll get to take in beautiful views of the water and city skyline. During summer, make a day of it by bringing a picnic and swim suits to cool off on the beach after your walk.

 
Take a stoller-friendly hike throufh Boston's only salt marsh. Belle Isle Marsh Reservation photo courtesy of On the Grid

2. Belle Isle Marsh Reservation — East Boston

You don’t have to travel far to discover the magic of Boston’s last remaining salt marsh at Belle Isle Reservation. There’s an accessible stone-dust trail that provides boardwalk access, so it’s a piece of cake to push a stroller here. Stop on one of the stone benches to watch birds in their natural habitat and catch planes taking off and landing at Logan. 

Stroller-Friendly Hikes near Boston 

3. Breakheart Reservation — Saugus and Wakefield

The 652-acre Breakheart Reservation contains two freshwater lakes, a hardwood forest and scenic views of the Boston area. If you’re pushing a stroller, we recommend that you take the gently sloping, one-mile paved path to Pearce Lake. It’s nicely forested and the lake even allows swimming, so pack your suits if it’s a hot day.

 
World's End trails formed along what used to be carriage roads. Photo by R.Cheek courtesy of The Trustees

4. World’s End — Hingham

Hike the century-old cart paths with your stroller to take in peaceful wooded areas, salt marshes, and views of Boston. Designed by Frederick Law Olmsted, World’s End was once a harbor island, but is now much more accessible. And at only 15 miles from Boston, it’s an easy drive for a lovely escape from the city.

Stroller-Friendly Hikes Worth the Drive

5. Appleton Farms — Ipswich and Hamilton

Visit one of the oldest continuously operating farms in the country when you take a trip to Appleton Farms. There are six miles of flat or gently rolling footpaths, bridle paths and farm roads on this Trustees of Reservations property that are just begging to be explored by stroller. You can also observe the afternoon milking or say hi to animals like sheep, goats, and chickens while at the farm.

6. Beaver Brook Reservation — Belmont

The Beaver Brook splash pad and playground are a popular summer destination for families. An accessible loop trail leading from the parking lot is another big draw for anyone pushing a stroller. Warm up on the three-quarters of a mile hike then, if it's summer, splash in the water to cool down.

 
Get your little ones excited to hike while they're still in a stroller. East Over Reservation photo by Tom Kates Photography courtesy of The Trustees of Reservations.

7. East Over Reservation — Rochester

While there’s still some agricultural work going on at East Over Reservation, much of the land is now being left to the area’s wildlife. Cart paths and flat fields and woodlands provide ample paths from which to take in the pastoral reservation, including its stunning stone walls. Also be on the lookout for a variety of bird species, rabbits and other native creatures at this Trustees property.

Explore Francis William Bird Park with strollers or bikes. Photo courtesy of The Trustees of Reservations

8. Francis William Bird Park — Walpole

The three miles of flat, tree-lined paths in Francis William Bird Park are perfect for strolling while pushing a carriage. Take in ducks swimming in ponds, grassy meadows, stone arches, and peaceful streams on your walk. Then let the kids blow off some steam at the park’s playground.

 
Some stroller-friendly hikes show families some gorgeous sights. Stevens Coolidge pathway photo courtesy of The Trustees

9. Stevens-Coolidge Place — North Andover

You can literally stop and smell the flowers at the Stevens-Coolidge Place, which features gorgeous garden paths perfect for stroller strolling. Not only are the flowers available for smelling, they’re also yours for the picking. That’s right, the Trustees allows visitors to bring home some of the beauty of the estate during the summer when they open the cutting garden to the public.

10. Rocky Woods — Medfield

Explore footpaths and former logging roads in this 491-acre reservation that contains both woods and wetlands. There are a few trails at Rocky Woods that are particularly good for stroller hiking. The 0.75-mile loop around Chickering Pond is ideal. And the Bridle Trail and Loop Trail are short, flat paths that traverse the wetlands.

Originally published 11/20; updated 4/23