Looking for the best trails around Fairfield?

Explore the best rated trails in Fairfield, CT, whether you're looking for an easy walking trail or a bike trail like the Fairfield Hills Campus Walking Trails and Norwalk River Valley Trail . With more than 82 trails covering 625 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

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.

Mosholu-Pelham Greenway

long but decrepit

April, 2025 by vbergerg_tl

Hadn’t ridden in at least 10 years; took it out from Van Cortlandt Park to Orchard Beach, City Island and the Country Club/Pell mansion areas . It is now in horrid shape. Patches bumps ruts. And more hills than I remembered LOL but that’s on me. But the bumps and holes do make hills harder. And also road crossings. No more FOMO

Heritage Trail (NY)

Heritage trail update!

December, 2024 by flywithme_tl

Great trail a must do . FYI bridge #1,2,3,4 were under construction but are now complete and the trail is open complete . When in Monroe just before overpass there is a good burger and place called Wayback burger . You have to pedal through a gas station lot but it’s next door .

Accordion

Harlem Valley Rail Trail

Everything you could ask for

October, 2024 by robert.richter89

I rode the entire 24.7 mile southern portion of the Harlem Valley Rail Trail on a beautiful fall day. The HVRT offers everything you could want from a trail experience: a fully paved surface, mostly flat, beautiful scenery (especially in the Fall) and a perfect mid-point trailhead to grab a bite to eat.

I don't recall seeing any water fountains along the trail although the trailhead in Millerton offers many options for places to eat or resupply. The HVRT offers a myriad of scenery changes from farmland, quiet streams, distant hills to quaint towns. I have ridden many paved rail trails in the past and the HVRT is one of the best with almost no surface imperfections for the entire distance. There are many trailheads along the entire trail giving many distance options. All this adds up to a perfect trail in my opinion!

Harlem Valley Rail Trail

trail is complete now but map not updated

October, 2024 by vbergerg_tl

Map is 6 months out of date

Vanderbilt Motor Parkway

Ride from Alley Pond to Citifield

October, 2024 by peterosenrosen@gmail.com

This trail continues 8 miles from Alley Pond Park all the way to Flushing Meadows Park, home of the 2024 World Series champion NY Mets! You only have to cross 3 streets for the entire ride. You continue past Cunningham park to peck fields then to Kissena Park, Kissena Corridor Park, then alongside the Queens botanical garden. It’s pretty flat, nicely paved, and you can safely ride it at night. Leave your

Old Erie Path

Good Connector Trail

October, 2024 by cehersh

We recently did a loop ride, crossing the George Washington Bridge and Mario Cuomo Bridges. This trail was a seamless connector from Rt. 9 and the town of Sparkill to the MCB. It's fairly narrow with occasional views across the Hudson River and the bridge. The condition was pretty good, gravel/dirt.

Bronx River Greenway

A Bit Disjointed

October, 2024 by cehersh

We attempted to ride the entirety of the greenway in two halves, north and south. North have was pretty good--a lot of raised roots on pavement--from Valhalla and south to Bronxville. The southern half began with an abrupt dead end below Bronxville, followed by miles on road. We eventually linked up with a bike lane alongside roadways that led us as far south as Bronx Zoo. Overall, the trail lack good markings and directives. We were disappointed with the southern section of greenway and aborted plans of continuing to the East River. Wanted to like it!

East River Greenway

Under Construction

October, 2024 by 8myn77627t

The East River Greenway is under construction. There is no access between 76th and 71st streets. The newly built portion between 71st and 52nd streets is quite nice. The section between 52nd and 37th still needs to be built. Further downtown, the greenway is closed south of 23rd until about the seaport. Hopefully it’ll be ready for next spring.

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

Saddle River County Park Bike Path

Beautiful Trail/No E-bikes Allowed

September, 2024 by stakrx

We had a beautiful day riding this trail! There were a lot of people, however, that's to be expected on a wonderful Sunday afternoon. The only downside was that we were stopped and given a warning, with my name taken and entered into the officers computer, by a County Sherif officer that e-bikes are prohibited in all Bergen County parks. Unfortunately we won't be back to this trail again.

William R. Steinhaus Dutchess Rail Trail

Hopewell Junction

September, 2024 by flywithme_tl

Went from the Thuway area in Poughkeepsie over the walkway and ride to Hopewell junction .Nice trail well groomed , paved not much to look at but very cool what the volunteers did to the RR depot , signal house and pavilion, the depot museum was great . Went to Daddy O’s restaurant on the trail , good food . The NY empire trail continues along live tracks goes I believe quite far .

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