Explore the most popular kid friendly trails near Winchester with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

One of the best hiking trail in the Boston area. The views is absolutely incredible and the sunset is wonderful too. This trail is relatively short so I usually combine it with other trail.

I also seldom complete this trail without a detour up Bear Hill as well. I enjoy the climb and the view from Bear Hill tower. And other times, I combine it with the trail that goes through the Middle and South Reservoir as well.

walking
4 months ago

Fairly easy trail, conveniently located. Long Pond is nice, but there aren’t many other interesting features.

hiking
6 months ago

Parking lot at (42.4496220,-71.1257951). Nice, short walk.

walking
9 months ago

Principally a pine forest on shallow soil over glacial stoney rubble. Mostly ~50 year old tree. Just few older. The trail rounds the small shallow lake mostly above. Petty views of that water. At the highest point a short detour to the west reveals an excellent vista. Pine forests, in my opinion, are a bit dull. The Fells are popular, this trail is less crowded than others.

hiking
11 months ago

hiking
11 months ago

hiking
Tuesday, July 25, 2017

hiking
Tuesday, July 25, 2017

Thursday, June 30, 2016

Wednesday, June 29, 2016

walking
Sunday, October 25, 2015