Hit the Trail: Boston’s Top 10 Stroller Hikes to Get Your Family Moving

1. Deer Island Trail

Deer Island Trail is a heavily trafficked loop trail located near Winthrop, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail is primarily used for walking, running, nature trips, and bird watching and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

This path is paved with very little change in elevation. The path offers stunning views of the ocean, of Winthrop, and of the nearby islands.

Distance: 2.7 miles
Difficulty: Easy

2. Boston Harbor and Castle Island

Boston Harbor and Castle Island is a 2.2 mile moderately trafficked loop trail located near Boston, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail is primarily used for walking, running, bird watching, and sea kayaking and is best used from April until October. Dogs are also able to use this trail.

This is a very beautiful area just south of Boston. You will walk around an enclosed bay past a beach, a WWII memorial and then to one of the country's most famous forts which was built to defend the city of Boston. The lawn around the fort is also perfect for a picnic lunch. Keep your eye out for planes overhead (close overhead) from Logan airport as well as kiteboarders zooming around in the bay.

Distance: 2.2 miles
Difficulty: Easy 

3. Charles River Pathway Short Loop

Charles River Pathway Short Loop is a moderately trafficked loop trail located near Boston, Massachusetts that features a river and is good for all skill levels. The trail is primarily used for walking, running, bird watching, and road biking and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

This leisurely ride takes you to some of Boston's wonderful waterways, following the beautiful and historic Charles River on both the Boston and Cambridge sides as you make your way towards Boston Harbor. This tour is an excellent introduction to the paved bike paths and includes some of the best views of the city. This area is great for children and inexperienced riders.

Distance: 3.1 miles
Difficulty: Easy

4.Charles River Sourthwest Corridor Trail

Charles River Southwest Corridor Trail is a lightly trafficked loop trail located near Allston, Massachusetts that features a river and is good for all skill levels. The trail is primarily used for hiking, walking, nature trips, and bird watching and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

Distance: 3.5 miles
Difficulty: Easy

5. Mary O'Malley Park Loop

Mary O'Malley Park Loop is a loop trail located near Chelsea, Massachusetts that offers scenic views and is good for all skill levels. The trail is primarily used for walking, running, and nature trips. Dogs are also able to use this trail but must be kept on leash.

Distance: 1.6 miles
Difficulty: Easy

6. Jamaica Pond and Victorian Jamaica Plain

Jamaica Pond and Victorian Jamaica Plain is a heavily trafficked loop trail located near Boston, Massachusetts that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail.

Distance: 3.2 miles
Difficulty: Easy

7. Fresh Pond Reservation Loop Trail

Fresh Pond Reservation Loop Trail is a moderately trafficked loop trail located near Belmont, Massachusetts that features a lake and is good for all skill levels. The trail offers a number of activity options and is best used from March until October. Dogs are also able to use this trail.

This is a nice paved walk around the 155-acre Fresh Pond Reservoir. There is one main path around the pond with options for short side trails. There are three main entrances at Alewife Brook, The Cambridge Water Works, and Glacken Field but you need to be a Cambridge resident to park here.

Distance: 2.5 miles
Difficulty: Easy

8. Minuteman Bikeway Trail

Minuteman Bikeway Trail is a heavily trafficked point-to-point trail located near Arlington, Massachusetts that features beautiful wild flowers and is good for all skill levels. The trail offers a number of activity options and is best used from April until October. Dogs are also able to use this trail.

This is a former right-of-way rail trail. It extends from Bedford, MA to Cambridge, MA. You will pass by Sly Pond and other historical parks and monuments on the way. It is all a paved, gentle path and very popular.

Distance: 10 miles
Difficulty: Easy

9. East Boundary and Stony Brook Path Loop

East Boundary and Stony Brook Path Loop is a moderately trafficked loop trail located near Hyde Park, Massachusetts that features a lake and is good for all skill levels. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail.

Distance: 1.8 miles
Difficulty: Easy

10. Upper Charles River Reservation Boardwalk

Upper Charles River Reservation Boardwalk is a moderately trafficked out and back trail located near Wellesley, Massachusetts that features a river and is good for all skill levels. The trail offers a number of activity options and is best used from March until November. This is a peaceful paved path that is mostly shaded along the Charles River.

Distance: 0.9 miles
Difficulty: Easy