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 Norwalk River Valley Trail and Ridgefield Rail Trail . With more than 79 trails covering 614 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

Ocean Parkway Coastal Greenway

Enjoyable Ride

June, 2024 by manselmo77

One of my favorite rides of LI. Good speeds/pace going east. Return headwind can be tough.

Ellen Farrant Memorial Bikeway

Easy Ride

June, 2024 by manselmo77

Flat, great breeze and plenty of sun. Beautiful views heading down to Jones Beach then connect to Ocean Pkwy. Easily put in 20-30 miles round trip.

Heritage Trail (NY)

Heritage trail

June, 2024 by flywithme_tl

A must ride stopped in Middletown for a bite to eat .

Accordion

Air Line State Park Trail

Get outta here. Put an asphalt trail down or stop wasting our time.

June, 2024 by db7178

Get outta here. Put an asphalt trail down or stop wasting our time.

Putnam Trailway

meh

June, 2024 by vbergerg_tl

Finally reached it from the North County trail way and was both surprised and disappointed. Some nice spots but mostly odd hills and backend of towns. Expected it to be much nicer. Now I’m trying to figure out the road connections in Brewster to get to the better reviewed Maybrook.

Ellen Farrant Memorial Bikeway

Bad Repair Work

June, 2024 by ph7trhf8fg

Was good until they did some repair maintenance on the pavement a few years back. Now is got bumps and humps along the entire length. Really poor quality work.

Pequonnock River Trail

Bring your phone with GPS

May, 2024 by sboaters_tl

My wife and I did this trail on touring bikes, starting at Glenwood Park in Bridgeport, and proceeded northward. Easy to follow until Twin Brooks Park where the trail joins the park trails but there is no signage from here northward. Nice surface but we had to stop NUMEROUS times to look at our GPS to determine our location and which trail/path to take. Then finding the Tait Road starting point for the next section was a challenge. Either print out the Trail Description and have a map, and/or have your phone handy as there are very few, if any, signs showing where the trail goes. A nice series of trails once you find them but don't expect ANY directional advice.

North Shore Rail Trail

Relaxed ride for family

May, 2024 by qfranco10

Yes it's along powerlines, but the ride is nice and easy, there are a few places to stop and enjoy a break. Most road crossings have crossing lights.

Old Putnam Trail

Short ride through Van Cortlandt Park.

May, 2024 by steve.schwinn

Road this fully paved trail, known as the Putnam Greenway in Van Cortlandt Park, in connection with the South County Trailway as an out-and-back starting from the Tarrytown Lakes Park Parking Lot on Neperan Road (1 mile connector trail to the junction of the North and South County Trailways). About a 35 mile round-trip. Trail is in very good shape but a bit narrow considering it’s busy with runners and walkers, especially on weekends. Be sure to check out the very impressive Grand Central Stones along the way.
Part of the Empire State Trail.

South County Trailway

Great trail with seamless trail connections at both ends!

May, 2024 by steve.schwinn

Road this fully paved trail in connection with the Old Putnam Trail (also known as the Putnam Greenway) as an out-and-back from the Tarrytown Lakes Park Parking Lot on Neperan Road (1 mile connector trail to the junction of the North and South County Trails) to the south end of Van Cortlandt Park. About a 35 mile round-trip. Trail is in very good shape with only a few root heaves. Note that the Old Putnam Trail is significantly narrower and busy with runners and walkers, especially on weekends.

CTfastrak Multi-Use Trail

Trail starts downtown New Britian, easy to find. Trail was clean, well marked except when you hit the main road for a little distance. Not a lot of people on 5/25/24. There's not a lot to look at but a nice 4.4 Mile trail.

May, 2024 by carlosccalhoun

Trail starts downtown New Britian, easy to find. Trail was clean, well marked except when you hit the main road for a little distance. Not a lot of people on 5/25/24. There's not a lot to look at but a nice 4.4 Mile trail.

Old Croton Aqueduct Trail

great view the whole time

May, 2024 by smashwin111

This and the Erie Path on the other side of the river are relatively flat, and I rode both easily on a hybrid. The view on either side of the river is really nice the whole time, because your are just elevated enough to see the river clearly the whole time. Also Tarrytown is a nice stop. I did this in two legs - Yonkers to Tarrytown, and Tarrytown to Croton Reservoir. The reservoir at the end is a nice destination.

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