Explore the best rated trails in Natick, MA, whether you're looking for an easy walking trail or a bike trail like the Southern New England Trunkline Trail and Heritage Trail (NH) . With more than 119 trails covering 748 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.
The claim of this being a 61 mile trail is very deceptive. Almost 40 miles of this trail is nearly unrideable except for mountain bikes (and even that would be unpleasant). We are experience riders and were on hybrid bikes with wide tires and front suspension. And while our plan was to cycle 40 miles from Willimantic to E. Hampton, we only did the first 10 mile section from Willimantic to James L. Goodwin State Forest.
The trail started out as just OK, but deteriorated in less than 2 miles. After crossing S. Brook Rd, the trail the trail was extremely gnarly and super overgrown. When we reached Goodwin State Forest, we were so happy to bail out and call it quits! Luckily, we had a SAG vehicle with us so we weren't forced to cycle back over the same awful trail.
Be warned, the entire trail we rode from Willimantic to Goodwin Forest was large, loose gravel, and the scenery is incredibly boring. There are places where the trail is extremely rough. At S. Brook Rd. the trail becomes unrideable, expect by maybe some die-hard mountain bikers. We used our SAG van to pop into other points along the trail from Goodwin to E. Hampton the trail only seemed to get even worse.
Honestly, just a really unpleasant ride.
My husband I decided to ride this trail on our visit to Boston. We parked at 31 McKenn Street in Waltham and rode in towards Boston, then crossed the river to ride back on the other side. First, I'll start with the positives. It has areas with nice shade and the views along the river are neat. Now for the negatives. The trail boasts it is all asphalt. It is not. There were many spots with packed dirt surface. Even though I don't like riding on anything but asphalt or concrete, this at least was pretty smooth and level. NOT compared to the badly maintained asphalt and concrete. The vegetation needed to be trimmed, the path was NOT marked at all (luckily my husband had a map on his phone), many sections were very narrow, not wide enough to have two bikes pass and the asphalt had many cracks that I had to be careful to watch for. Sorry but whoever has the contract to maintain this trail is falling down on the job. Boston is such a neat city so I won't let this trail color our experience as totally bad, but you couldn't pay me to ride this trail again.
We (5) Friends Have Biked This Trail in It’s Sections from E. Hampton to Willimantic for Many Years. We Have Always Considered it to be 4-5 Star Rated, (For a Gravel Trail). Since 2015, We Have Switched to E-Bikes which makes the Trail 3x more FUN !! Having the Best of Both Sun & Shady Sections, It Has Only One small Section of about 300’ Near the Start leaving E.Hampton Where it’s sandy & .Loose
rode 7-30-25 parked at Symmes Dr in bus depot lot - no directions for where to park. Mile markers are facing the trail, instead of perpendicular , so they can't be easily read while riding - missed a few along the way. Also signage at entrance areas should include direction and milage to either end. Thought we could hook up to the Derry trail, but that didn't happen - couldn't find it - again, signs would help !
Rode on 7-26-25 Needs mile markers at Windham end. Slight incline from Salem to Windham. The Windham trail is paved, but turns to dirt when you reach the Salem trail. Turned around and rode back to Windham.
the Windham trail is paved, but turns to dirt when you reach the Salem trail.
Turned around and rode back to Windham.
rode trail july 28, 25 from Winchendon - slight uphill, going south to Gardner. Adding mile markers would be nice ! and directions at N.Ashburnham Rd to Old Gardner Rd. Newly paved from entrance off
Old Gardner Rd to Gardner town line. Path to avoid watery underpass was paved on one side of street.
It is such a lovely trail. The view is gorgeous, either from the ocean or from the land. It goes through a few towns, all lovely and friendly. There are shops along the trail for you to stop by for ice cream, coffee or lemonade. There are a few road crossing, but the cars are very friendly and stop to let cyclists cross. The destination Bristol is just beautiful! Some areas are in the open, so the wind can be your friend or not …..
It is a great trail for all seasons. Parking available in Ayer, Groton, Pepperell and Nashua
It is a very well maintained trail. My favorite part is between the heart pond and the NARA park. More road crossing beyond that region in both directions
It’s a nice paved path, shaded half way through. Good for families with kids. Parking is free but though to find, suggests keep following the path till you find parking. There are several options along the way from the eastern end of the trail. Few food and restroom options, within coffee or mall shops. Public restrooms are very limited at least when starting from east end. We went only half way and back, with kids. Looking forward to finish the second half soon.
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