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

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Holliston, Massachusetts Map
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walking
1 month ago

Simple trail system, with not a lot of crowds, so very enjoyable as an early morning or evening walk.

Nice property. Lot's of mountain bikers but trail runners and rock climbers too. I headed north from the Adams Street parking lot up to the beaver brook. The beaver house was really cool and very close to the trail. I continued up to the College Rock climbing area where a bunch of folks were top roping. Lots of erratics, impressive ones too. Trail is plenty rocky but I love that. This is an impressive property! Enjoy

trail running
7 months ago

A very pleasant property. You can combine a trail run or hike with some time on the Upper Charles rail trail. The rail trail was busy with soccer Mom's walking their dogs and gabbing away. I went south and just worked my way down to the Idylbrook property and playing fields. There are some wetlands, water fowl, and beaver dams to see on the way. Very nice overall. Then I continued clockwise back up to the Wenakeening Woods and some playing fields there. I did start my GPS in the woods so be aware of that. A nice trek for sure! Enjoy.

Very nice walking trail, nice views of the pond with many lilly pads and a huge nest in the middle.

trail running
Wednesday, October 05, 2016

Short but very runable loop. Trail is clearly marked and kept up very well. No dogs allowed (though I have seen them in there). Only a few parking spots but they are free. Would not recommend parking out on Clinton ST.

cross country skiing
Wednesday, October 05, 2016

Nice little loop and an easy ski. Only a few parking spots but at least it's free.

Sunday, July 10, 2016

Follow the map on the trail sign Do not follow the loop that is listed on all trails. this Trail apparently existed at one time but no longer is active we had half of the trail was bushwhacking.

hiking
24 days ago

trail running
7 months ago

trail running
7 months ago

trail running
11 months ago

Sunday, April 30, 2017

hiking
Thursday, March 30, 2017

trail running
Saturday, January 28, 2017

hiking
Sunday, May 10, 2015