Explore the best rated trails in Holliston, MA, whether you're looking for an easy walking trail or a bike trail like the Southern New England Trunkline Trail and Swampscott Rail Trail . With more than 112 trails covering 702 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 trail in Cranston was repaved recently. There weren’t even lines painted yet! It was a smooth ride. There was one detour due to the paving, but it was an easy ride on a side street.
I'm in love with this trail. Much of the trail path is dirt, but there is a new area with fine gravel. I find this such a peaceful trail and consider it to be in good maintenance. Thanks to everyone that maintains the trails.
This is a decent trail but there are a few things to note: No parking lot on Marlboro end but I did find parking on a side street. The trail has many street crossings, especially when you are in Hudson. Some of the crossings are busy intersections. The trail ends in Hudson but you can bike along rte 62 for a few miles, then down a side street to pick it up again in stow. That portion of the trail will take you to action. The guide says this is 10 miles but I’m not sure if the Marlboro to Hudson section is 10 miles or if it is 10 miles with the stow to acton portion. Marlboro to Hudson didn’t seem like 10 miles. I wouldn’t go out of my way to do this tri
We had a great ride! 6.6 miles. Beautiful day!
Wellington Greenway Trail is good place to ride my bike underpass the MBTA purple and orange line trains. Ducks walk by the river pond. I have seen yacht boats there.
This section (8/2024) is about 5 miles long. It goes through woodland and past leafy backyards, but it runs alongside the towers for a high-tension power line. Trees have been clear-cut about 25 feet on both sides of the trail, so there's no shade along this section. But the trail is wide, very straight, and smoothly paved. It has a few small ups and downs and crosses four or five quiet roads before it comes to a traffic signal at the intersection of Routes 126 and 27. Just beyond, the trail turns to crushed stone with a few sandy patches. There's a large supermarket and shopping center adjacent to the trail at that point.
We parked in West Concord and decided to ride south to Sudbury. Beautiful trail — ends 2 miles from where we parked with a locked gate. BUT… there is more trail on the other side. There is a nice, paved switchback up to a crossing at Powdermill Road. All marked with great signage. The way down on the other side is very steep and not paved—but manageable after dismounting. Trail is just as beautiful on the other side. We didn’t make it quite to the end because I got a construction-based flat at North Road (the Davis Field parking lot). I didn’t notice that they hadn’t paved the transitions at the road crossing and pinched a tire. Oh well. Hopefully, by the time you ride the construction will be complete and you can just enjoy the scenery!
This isn’t one of those trails that you can zip along mindlessly, since it’s stitched together with various public spaces and has quite a few street crossings and pedestrians. But I found it to be a leisurely ride through Boston’s urban landscape. Northeastern University’s campus, Museum of Fine Arts Boston, and the Fenway and Back Bay neighborhoods are all easy off-shoots if you’re up for city streets with bike lanes. The park also has a cool backstory as a planned highway connection between I-95 and Boston that was blocked by community activists in favor of mass transit, public spaces, and a bike trail. I’m sure it’s busy during peak commuting times, though it wasn’t too bad on the Sunday morning I visited.
Mile 17-7 going south from Woonsocket the trail is marked. Very enjoyable ride.
Great for walking most intersections are low traffic areas. Peace and quiet in the middle of town.
Love the beautiful trail, but horseback riders should have a manure bag on the horses to catch their droppings. Not fair to others walking the trail.
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