Looking for the best trails around Old Saybrook?

Explore the best rated trails in Old Saybrook, 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 39 trails covering 309 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

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

Accordion

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!

Moosup Valley State Park Trail

Horse

August, 2024 by janeyac1

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.

Moosup Valley State Park Trail

It’s nice!

August, 2024 by revgil

When I first rode this trail in 2012, it was horrible, even though I had a mountain bike. My wife and I just settled on driving over to Coventry, RI to ride; Moosup was next to impossible. But several months ago work began to get it fixed up. What a nice job, with drainage, a new stone-dust surface, and nice fencing. We have ridden trails all over town country, and this is one of the nicest anywhere. Now, if RI will finish the Washington Secondary Trail from Summit to the state line, I could ride all the way to Providence without having to go on the road!

North Shore Rail Trail

great trail

August, 2024 by gatogo4

Easy riding trail. Lots of crossings There are no center posts on some of the crossings making the crossings much easier to navigate. Hope the rest of the center posts could be removed

Mattabassett Trolley Trail

What's the point....

August, 2024 by jbarrett01

......of having a trail where there is nowhere to park???

Quinebaug River Trail

southern section has been lengthened a bit.

August, 2024 by seraph101

Southern end of the trail has had about .3-.5 miles of paved section added.
Along the river to Quandock Brook.

Moosup Valley State Park Trail

Open again.

August, 2024 by seraph101

There is still some work being done. mostly placing fencing. but, the surface is finished, and the trail is open. Public making use of it again.

Mostly stonedust, with a few paved sections. New signage/crosswalks for road intersections. signs, no blinking lights.

new parking. 3 new lots.
A new parking lot has been added to the corner of Railroad ave and Spring lake rd, just off 14 and 14a in sterling, towards the "end" of the trail, at the ct state line.

A parking lot has been added on industrial park rd, in sterling, up the big field, next to the trail.

Another small parking lot added to Barber hill road, off n main st, across the river next to the trail in Moosup.
the .7m paved section from the start to Barber hill rd is unchanged.


2 park bench locations.
one off Main street in sterling. the north west side, next to Weidele's pizza and pub. (which recently moved from rt 14 to here).
another next to the "rainbow bridge", off the new Babcock rd access.

The project was 3.85million.
Major work done to fix drainage. The vast majority of which does seem solved. Theres a couple places with some problems still. (particularly about .5miles east from rt 14 in sterling, towards babcock/providence rd). some runoff, and one large puddle still.

The bollards blocking the bridge over the moosup river between sterling and moosup, .3 from sterling have been removed. This section is now wheelchair/stroller/bike carriage friendly.

The bollards for the rainbow bridge over Providence road have not been removed. the clearance is 36". (note, the north east side of the trail is only 34". the right side, coming from the paved section. the left side is 36")
plan accordingly.
Bypass is not quick and easy. From moosup, turn up Babcock road access, then right/south onto Providence road, go under the bridge, down to 14A/plainfield pike. Turn left/east on 14a, continue to taking a left onto railroad ave. up to the new Railroad ave trail access.
14a is a fairly heavy use road with little to no shoulder.

The .5mile paved section from Spring lake rd, to the bridge over Providence rd has also been repaired, with pavement.

Official renovations end at 14a, and the state line.

Atvs and dirtbikes are already tearing up the trail... hoping regular foot/bike traffic gets them to stop. not sure who to call, state police, or deep.


The section from RI state border to paved Washington secondary bike path is getting worse.
from ct/ri State line to Lewis farm road its dirt.
heavy use from ATVS/dirt bike is creating moguls and puddles. its still possible to go around, but is getting less fun and manageable every year.
The levee/valley for Carbunkle pond is very soft sand. roadbikes/strollers/wheelchairs beware. get off and walk, and/or try to go on the grass to the north side of the trail. a huge washout at the trail to carbunkle pond.

from lewis farm road, to hopkins hollow rd is railroad grade gravel. perpetually wet. a very large puddle at the entrance of hopkins hollow rd.

from hopkins hollow rd, to log bridge road/summit general store/102. dirt/gravel, and moguls, moguls moguls. past the wind turbines, there is also a large puddle that can be bypassed by going up into the woods.
also a few trees down.

Best to just bypass this section, if on roadbike or all terrain. if coming from Washington secondary, head north up log bridge road, then west on 117. take the right in Green, staying on 117. at Lewis farm road(a dirt road), you have a choice, take it to the trail, and do the slightly rough section between lewis farm rd, and 14a. Or, just stay on 117, continue to 14, taking a left onto it, and continue to 14a, taking a left onto 14a. 14a to the trail again. Renovated section.

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