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Stroller-Friendly Trails

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Strollers are good options for families with children not quite ready to explore the outdoors on foot. But both traditional strollers and the high-tech, state-of-the-wheel versions now available still work best on good trail surfaces.

Here is a list of Trustees properties that feature pathways that are easy on strollers (and on the parents who power them!). Check out these destinations where you can push without too much push-back – then add your own favorites.

Lowell Holly, Mashpee and Sandwich
Make your way along a half-mile, private road that leads to this peninsula jutting between a pair of freshwater ponds, then enjoy the American holly trees and other planted species along undulating carriage roads.

East Over Reservation, Rochester
Formerly part of a larger working farm, this agricultural landscape includes cart paths and other routes that lead through a generally flat mix of fields and woodlands and past exquisite, double-faced stone walls.

World's End, Hingham
The century-old cart paths (pictured above in main photo) and wooded allées that grace this South Shore peninsula today draw parades of stroller-pushers. Ascend the top of Planter’s Hill on a grassy pathway for memorable panoramas of Boston Harbor.

Appleton Farms, Ipswich and Hamilton
Lots of grass and gravel here, thus relatively easy to negotiate with strollers. More than 90 percent of the terrain is flat or gently rolling and the Grass Rides on the southwest side beckon “off road” strollers.

Stevens-Coolidge Place, North Andover
Your young ones can soak up some history and horticulture as you wheel them through the gardens behind this renowned country house. Bring a picnic and park the strollers by the lovely lawns.

Rocky Woods, Medfield
Logging roads initially laid out two centuries ago continue to fulfill their transportation roles – but for contemporary toddler conveyances. The route around Chickering Pond and the Bridle Trail loop are both ideal.

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