Looking for the best trails around Webster?

Explore the best rated trails in Webster, MA, whether you're looking for an easy walking trail or a bike trail like the Southern New England Trunkline Trail and Fresh Pond Bikeway . With more than 97 trails covering 731 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.

Recent Trail Reviews

Washington Secondary Bike Path

Trail Construction

September, 2024 by nnnkfpw7zq

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.

Ashburnham Rail Trail

Very Enjoyable, Much natural beauty

September, 2024 by tammy.bucklew

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.

Moosup Valley State Park Trail

What an improvement!

September, 2024 by bopflu

When I attempted this trail in 2022, I called it "the worst ride of my life." I got covered in mud, and the numerous puddles teemed with mosquitos. But what a difference two years made!

The trail has been vastly improved, now offering a highly pleasant ride through Connecticut's Route 14 corridor. It does, however, become rougher shortly after you cross Route 14-A near the Rhode Island state line. I only hope further improvements will be made.

Accordion

Assabet River Rail Trail

not what I expected

September, 2024 by chleary11

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

Air Line State Park Trail

We had a great ride! 6.6 miles. Beautiful day!

September, 2024 by susanmazur13

We had a great ride! 6.6 miles. Beautiful day!

Wellington Greenway

Trail by MBTA station

September, 2024 by oneadventureroad

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.

Mass Central Rail Trail

Weston-Waltham section

September, 2024 by msandman1943_tl

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.

Southwick Rail Trail

Very busy on sunny weekend, well kept trail

September, 2024 by mdnkcn

We started going north on Copper Hill Rd East Granby Ct parking area and finished the trail in Westfield MA. Trail was all asphalt and in good shape. Most of the trail was scenic farmland but toward the north end going toward Westfield was some residential and city though still was plesent to the eye. Next time we plan to take the trail south at the Copper Hill Parking and take the trail to where it hopefully meets the Farmington River Trail

Bruce Freeman Rail Trail

Agree. GREAT Trail!

September, 2024 by 44s9k9tzxm

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!

Southwest Corridor Park (Pierre Lallement Bike Path)

Enjoyable urban adventure

September, 2024 by douglane

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.

Blackstone River Greenway

Mile 17-7 going south from Woonsocket the trail is marked. Very enjoyable ride.

September, 2024 by buckley02

Mile 17-7 going south from Woonsocket the trail is marked. Very enjoyable ride.

Hanover Branch Rail Trail

Great for walking most intersections are low traffic areas. Peace and quiet in the middle of town.

September, 2024 by buckley02

Great for walking most intersections are low traffic areas. Peace and quiet in the middle of town.

Find Nearby City trails

Accordion

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.