Find the top rated mountain biking trails in Litchfield, whether you're looking for an easy short mountain biking trail or a long mountain biking trail, you'll find what you're looking for. Click on a mountain biking trail below to find trail descriptions, trail maps, photos, and reviews.
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A friend and I did this ride today starting from Brewster to Hopewell Junction, continuing on the Dutchess Rail Trail for ~4 miles and back. The ride was excellent, a little over 50 miles with a gradual decent (~10 miles) on the way to Hopewell and ascent back. The trail was very smooth, there were a couple of spots on the Dutchess side that had growth into the trail and one downed tree blocking the way.
Great ride through the shawingunk mountains ! Trail was great bikes were awesome ! What a beautiful day !!
Haven't ridden the trail since 2023. Rode from Cheshire down to New Haven, Saturday July 19th. Absolutely awful; entire section needs repaving and upkeep. Constant cracks in pavement and much debris on surface; plus glass and homeless down by the Wharf. Connecticut should take notice from Mass and NY on trail up keep. Both states's trail are far superior to CT. Also, difficult to navigate at trail end in New Haven if you don't know the city; poor signage.
July 19 2025
Just rode from Pomfret west to the Rt6 overpass. Most of the trail is good riding except for some rocky sections, but the overgrowth is starting to close off the trail in sections. It is down to just one lane. It would be nice if the state could mow the weeds.
Use gps route its not well marked like others have said but part of the fun was planning the route and then finding your way as you go.
did trail 7 years ago. What a change!! Smooth all the way from Copake Falls to Wassaic!!!! Did 50 mile round trip then took a dip in the spring fed lake at Taconic Hills State park. Can walk to the lake from the trail head at copake falls. Also a nice state park with interesting sights. We stayed in Great Barrington , 10 miles from Copake Falls. Make sure you check out the Barrington Brewery. Great beer, great food.
Beautiful ride in the am was nice and cool and quiet Down hill to hopewell This time of year there are so many raspberries on the side of the trail going back to collect some for jam end of the week Being a rail trail the way back is just a slight incline Great Ride
Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.
Rough in spots but really nice ride !!! Would do it again ! Tough around the steep hill x2 , Tressel bridge !!! But nice scenery and cool breeze Pat and Kevin B
Section from New Paltz (and maybe a mile or two below, I haven’t checked) to a mile or so north of the Rosendale Trestle is superb. Just after the Women’s Studio Workshop is an interesting historical furnace chimney. But then the trail comes apart - chunky gravel and hills I wouldn’t want to come down, leading to Williams Lake (saw lots of landscaping going on but no one using that end of it recreationally). I returned to the Women’s Studiovia the road.
I rode 20.5 miles of the southern section of the Air Line Trail from East Hampton to Willimantic on a very hot day in June. This section of the Air Line Trail offers gorgeous scenery, peaceful seclusion and a tightly packed gravel surface that is in very good condition throughout. Despite the heat the trail is very shaded which provided much needed relief from the sun. There are a fair amount of road crossings, most are very small, quiet roads and all of the busier roads have warning lights that can be activated to let motorists know you are crossing.
The only two small complaints I have is there is a lack of signage along the trail. There is one very short on road section that I almost missed getting back on the trail due to there being no signage, I just rightly assumed the small unmarked path on the road was the way to get back on the trail. The gates at the road crossings are on the narrow side which can make navigating through the road crossings difficult. I feel these two issues do not at all detract from what this section of the Air Line Trail has to offer.
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