Explore the best rated trails in Westport, CT, whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Marcus J. Molinaro Northside Line . With more than 86 trails covering 626 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.
I rode the entirety of the Steinhaus Trail starting at Hopewell Junction and riding over the Walkway over the Hudson. On a very windy early April Sunday the trail was lightly used and everyone was very polite and practiced great trail etiquette including very attentive drivers at road intersections.
The trail itself is fairly wide, is well marked with mile markers counting up or down from Hopewell Junction depending on which way you are going and is in immaculate shape. I don't even recall a single bump, pothole or crack on the asphalt. The scenery is a mix of light residential, some commercial, a nice lake near Hopewell Junction and a good amount of tree cover.
I appreciate how easy it was to connect to the Hudson Valley Rail Trail via the Walkway over the Hudson which added to my ride.
I work the trail on NYE great walk what I recommend some great walking running sneakers great views burned a lot of calories planning to do it again when Late Spring Summer arrives
Old Erie is a unique and lovely gravel path distinct from the Clarke and Esposito paved trails. Easy to miss but very worthwhile IF you have the right bike. Somewhat chunky gravel and a few ruts so recommend at least 38mm tires. In exchange for bumps you get forest, nice elevation changes, beautiful views of the river, and a direct path connect to both downtown Nyack (shops, eats) and the new Mario Cuomo bridge path. But VERY important: the start of trail in Sparkill is a very dangerous 5-way intersection with blind spots... DISMOUNT here, wait, listen, walk it across.
During the summer, there are more than 2 stops along the way you can buy drinks and food.
27 mile total. On my way back, I was riding against the wind, so tired......
It's not too long, but watch out for sharp turns and steep climb onto the cross over bridge.
Also there were junkies in the Allie pond park parking lot asking people for money.
After reading many of the mixed reviews for this trail on TrailLink, I decided to keep my ride short but sweet by restricting it to what seemed to be the most picturesque - the portion between the historic Unionville train depot and the Riverside Nursery and Garden Center in Collinsville.
This part of the trail contains breathtaking views of the officially deemed wild and scenic Farmington River. In addition, since I did this in mid October, the river was a perfect reflecting glass for the amazing fall colors.
My ride was only a total of twelve miles out and back, but I now have the most perfect photos, videos, and memories of this Connecticut treasure!
The bike ride is easy and mostly flat with lots of locals getting their steps in and exercising their dogs. Surprisingly, I only encountered two other bicyclists on my early weekday morning ride.
After starting in New Paltz on the Hudson Valley Rail Trail and then crossing the Walkway Over The Hudson, I continued on to the Dutchess Rail Trail. I only went a few miles before turning around and heading back to New Paltz for a 21 mile ride.
The portion I rode is for the most part heavily forested, so if you like colorful trees in the fall or shade in the summer you'll love this. The trail is easy to ride, in amazing condition, and on a weekday morning in mid October lightly used. I especially appreciated the use of wood fencing in many spots which was the perfect architectural touch for this trail. Another highlight was Morgan Lake with its lovely swans and colorful trees reflecting upon the water.
I wish I would have had the time to venture further into the beautiful rural areas, but time was of the essence. I guess I have a reason to return and do the full length next time!
After pedaling down the Hudson Valley Rail Trail from New Paltz, I made my way onto the walkway. It was 7:30 on a brisk mid October weekday morning, and the bridge was not crawling with hordes of tourists (like me). Instead it was obviously primarily locals out jogging, getting their steps in on their walks, rollerblading, and walking their dogs.
The views are as expected - absolutely sensational and breathtaking looking both up and downriver.
After continuing across I proceeded to explore the Dutchess Rail Trail for several miles before heading back.
As luck would have it, when I returned the walkway was a completely different world. It was totally enveloped in fog, and you could no longer see the Hudson let alone fifty yards in front of you. The bridge was essentially deserted. Worst of all, I didn't get to do my selfies with a Hudson River background!
The walkway, combined with the rail trails on either end, is a must destination ride for bicyclists. What an unforgettable experience!
The history of the Long Island Motor Parkway (as it was first recalled) is revealed with signage along the length of the Parkway, including the site of the Jacob Johnson Family Burial Ground who appears in the 1830 Census as a "free colored man." At least two of his sons served in a segregated unit in the Civil War. He was a farmer in the area until retirement when he lived very close to Alley Pond.
The length of the entire park roadway, designated as part of the Greenway, has been repaved.
Review other park features when you come. In another area of the larger Alley Pond Park is found the oldest and tallest tree in NYC, already growing at the time of George Washington, known as the Alley Pond Giant. Hiking trails throughout the Park are well maintained.
We love biking the Airline and have used non electric hybrid bikes as well as e-bikes. Both work well. On 10/28/2023 we biked the section from Willimantic parking at the Connecticut Eastern Railroad Museum area and pedaled to Rt. 207 Lebanon Rd, Amston, CT. FYI, we're in our 60s and encountered no difficulties with the terrain.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
