Photo by P. Morotta
hike trustees challenge
mountains silhouette


With 120 places and hundreds of miles of trails to explore across Massachusetts, hiking Trustees properties is plentiful and varied. Not sure where to start? We've rounded up a few ideas for you here.

The Full List
Browse our entire list of places and discover your new favorite place today.

High Mileage Hiking Trails
Looking for trails with lots of miles? Here's our round up of properties with the most miles!

Summits & Views
Wondering if the long trek up our mountains and hills is worth it? The rewarding views from these summits never disappoint!

Easy Hikes
Whether taking a quick break from a busy day or spending a leisurely afternoon, hiking is an easy and fun way for you to enjoy the outdoors throughout the year.

Waterfalls & Streams
There's nothing like experiencing the magic of discovering a waterfall or a perfect stream during a hike.

Stroller Friendly Hikes
Strollers are good options for families with children not quite ready to explore the outdoors on foot. But both traditional and off-road strollers still work best on good trail surfaces.

Walks in the Park
Finding an easy enjoyable walk in one of our parks is as easy as, well, a walk in the park!

Random Place Finder
Up for a random adventure? Let our robot choose a place for you and let the exploration begin.

kids climbing on rocks

Dexter Drumlin in Lancaster