Looking for the best trails around Westbrook?

Explore the best rated trails in Westbrook, CT, whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk . With more than 43 trails covering 321 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

Hop River State Park Trail

Great place for a ride, scenery, and history

May, 2025 by traillink.qmsck

I recently rode this on a cool day in May from Manchester to Willimantic and back, so right at 40 miles. The trail is well-maintained and foot/bike traffic was light, even though it was a holiday weekend. Very scenic for long stretches and low elevation gain. I rode a gravel bike with 45 mm tires. On a road bike with reasonable tires, this should be do-able (I saw a couple of them), but there is one rough section of about 100ft (30m) where you would need to walk. There is also one underpass that is dark enough to use a headlight...but it's passable if you slow down. There are a number of places to read about the history of the rail line, as well as a few locations with fix-it stations with bike tools and air pumps.
One final tip: Google maps takes you to an intersection on Colonial Road for the Manchester trailhead...the parking lot has a tiny sign that is easy to miss.

Setauket-Port Jefferson Station Greenway Trail

Saw 2 Deer on Trail!

May, 2025 by mx546x87dm

This morning May 25, 25 we saw a doe and larger buck between east of Old Town Road.

Moosup Valley State Park Trail

Great Little Trail!

April, 2025 by 9q8skpdwwc

I rode the Moosup Valley Rail Trail a few days ago from Moosup to Oneco. The trail is in excellent condition all the way, and beautiful! I rode 34mm knobbies, but would have had no trouble on 28 slicks. The only irritants were a guy on a motorized scooter in Moosup and 2 guys on screaming dirt bikes going the other way a bit farther along, but they passed quickly. In Sterling, dirt bikers had dug shallow ruts into a short stretch of path, diagonal to direction of travel, which made it bumpy but not hazardous. Otherwise lovely! I wish Rhode Island would step up to the plate and finish the connector to its Washington Secondary path.

Accordion

Farmington Canal Heritage Trail

A few signs hold it back from five stars

April, 2025 by robert.richter89

I rode the entire northern section of the Farmington Canal Trail from Plainville into MA on a windy Easter Sunday. The trail itself is fully paved, in very good overall condition (there are a few bumps and cracks but nothing major). Simsbury offers a great stopping off point to get refreshments just a quick turn off from the trail. The scenery changes from light industrial parks, residential, marshes, a little farmland and some nice wooded areas.

I have one complaint that prevents this from being a five star trail. The signage could be better. There are times in the more urban areas that I lost the trail, a quick look at Google Maps got me back on and I never was too lost. There are a few signs that were helpful so just a few more would make this a five star trail.

William C. O'Neill Bike Path

smooth and clean

November, 2024 by walkinator007

This is my childhood bike path, it’s a lot shorter than I remembered now that I have the speed and endurance I do. Still a wonderful ride through the swamp and forests of south Kingstown, through peace dale and wakefield , to the beaches of Narragansett.

Washington Secondary Bike Path

Quite the good climb going south

November, 2024 by walkinator007

as of october 2024 this path is paved and quite nice.

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Setauket-Port Jefferson Station Greenway Trail

Great path but the abandoned warehouse is gone so seeing old building aspect gone, and they are not maintaining with the roots pushing up the road

September, 2024 by jrfarrell1991

Great path but the abandoned warehouse is gone so seeing old building aspect gone, and they are not maintaining with the roots pushing up the road

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.

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.

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!

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