Explore the best rated trails in Holliston, MA, whether you're looking for an easy walking trail or a bike trail like the Danvers Rail Trail and Swampscott Rail Trail . With more than 109 trails covering 636 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.
This bike path between Bristol and India Park in Providence was just what I had hoped for: picturesque views, charming towns and homes, beautiful foliage, and friendly people of all ages!
In addition, there were a few surprises. I discovered that this path is a definite paradise for bird lovers. It even passes right by an Audubon Nature Center accessible by the path! There were also many interesting historical aspects such as the Pomham Rocks Lighthouse, remnants of the old railroad, and the Squantum Association mansion. The best surprise and highlight for me was the Spooky Bottom Scenic Dock. Don't skip or miss this! I barely noticed the small sign for it. It's not spooky, and it's not a dock. It's a pier that will take you out into the bay for awesome views of the causeway, bay, and the Providence skyline including the state capital's green dome!
This path is obviously extremely popular with the community: walkers, joggers, bikers, dog walkers, and many parents pushing strollers. Also, I have never seen so many students on their way to school utilizing a path like this on their bikes. I must have seen at least thirty. That's a testament to the safety of the surrounding neighborhood and community!
I drove all the way from California to experience this trail, and I'm so glad I did. I've ridden my bike in forty-nine of our fifty states, and I definitely put this Hall of Fame trail in my top five favorites! A+, state of Rhode Island!
I traveled all the way from California with high expectations for this trail and I wasn't let down (except for the repairs being made on the damaged portion of the trail). It's all good. I made it work.
What an awesome trail for a mid October bike ride!
- The colors of the trees reflected upon the numerous ponds and lakes.
- The pleasant chirping and squawking of active birds.
- Leaves fluttering gently to the ground.
- A wide, smooth path carpeted in golden brown leaves.
- Historic buildings.
- Industrious squirrels.
- Old, historic stone walls.
- Deep, dark woods.
- Rolling, grass covered hills.
- Harvested pumpkins on a farm being sorted into bins.
- Goats, horses, and the friendliest trail users you could ever hope to cross paths with!
I took a leisurely four hours out and back and over 200 photos and video to capture my wonderful memories of this trail. Thank you Massachusetts and New Hampshire!
Contrary to the symbol on the map, parking is NOT available at the Fresh Pond end, even on Sundays, unless you live in Cambridge, and even then, "Permit Required". I drove almost two hours to get there and back, and never got to walk it.
The path is nice and cool in the summer due to lots of shade. Much of it has large sections of big tree roots, though.
Cheshire Trail South. Rode north from State Line Circle toward Kenne. We are experienced road cyclists, now riding gravel bikes. We are looking for reasonably surfaced longer trails and hoped this would be one of them. Sadly, we found this trail to be rocky, rutted, with lots of roots, and uncleared blowdown. The vigilance required to remain upright made it difficult to enjoy the beauty all around. The suddenly occurring steep inclines to roads seemed borderline dangerous. If we lived closer it would be a great trail to walk with the dogs
I have ridden this trail many times, and always enjoy it. It is well maintained, well marked, plenty of great places to park for a variety of stop/starting points. Several lovely bridges over roads that would be difficult or impossible to cross. A bike shop along the route, even EV charging stations at the lot by the West Concord train station, where you can also visit the lovely shops and cafes nearby!
Be aware that the section from West Concord towards the Sudbury expansion is well used by the nearby Middle school for after school activities and can be heavily congested during that time. Road cycling can be a challenge weekday afternoons when school is in session.
This trail is pretty much abandoned and mislabeled in the site description.
I went here expecting it to be asphalt like it says in the description, I intended to rollerblade it. Instead, I decided to walk it. The path is dirt and very much abandoned. It would be a very nice path after some updates and repair. It still gave a very nice view of the waterfall at the end of the path.
First: be aware that a recent storm has washed out a section of the trail about 2 miles from the Ayer parking lot in Sept 2023. People are portaging past it, but some set-ups might not work in this situation. That said, this is a great trail. Plenty of parking at many points along the way, some even have EV chargers!
This is a very fun and very well maintained trail. It crosses throught the heart of several cities/towns, so there is a lot to see. The trail is pretty flat for the whole duration, so it is an easy ride or walk.
Truly a nice ride this weekend. Packed surface, mixed terrain but nothing our Surly Ogre's couldn't handle. This was not a crowded trail but there were a spattering of walkers, bikers, dog walkers. Made you feel happy to be alive! Whoever is maintaining this trail - thank you!
I rode from Ayer to Nashua and back over 2 hours on Labor Day morning. It is a pleasant ride on a level grade and I was able to keep up a steady pace for the whole ride. The trail is asphalt and in sections there are uneven areas where possibly tree roots have displaced the pavement. It is a big improvement over the last time I rode in several years ago. At that time there were many small conical mounds projecting 2-4 inches above the pavement, again presumably due to tree roots. I hit one one that was in the shadows and was bounced clear off the bike. All those spots have been repaired as far as I could tell. 4 stars because of the pavement issues but a very nice and scenic ride (even accounting for the grouchy local man moving brush in a wheelbarrow along the trail who responded to my "good morning" with a "get screwed").
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