Find the top rated cross country skiing trails in Litchfield, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing trail below to find trail descriptions, trail maps, photos, and reviews.
Beautiful 1st ride on the Norwottuck Rail Trail. We parked at the Marshalls in Hadley (trail starts right behind the building) and road a little over 10 miles into EastHampton and back. It was a very easy ride (my 1st ride of this length) on asphalt.
The Northampton part, which is reallly the NORWATTUCK RAIL TRAIL is really 2 stars bc it's so confusing. Needs fundraising and signage. But the rest, Manhan Rail Trail, is really nice. 5 stars. We took photos to illustrate but I unfortunately deleted them by accident.
We had stayed at the Hotel Northampton & nobody could tell us for certain how to find the trail other than to mention the railroad tracks. We found a paved path by the tracks & headed left. We passed a stone that said <- BOS/NHV --> and that's all. (Couldn't imagine how Boston could be to the left or straight ahead.) Within about 20 minutes, that path ended by some really rundown stores. On an aerial Google map, it reads as NORWATTUCK RAIL TRAIL (& shows it as a hiking &rail trail on the east side of the railroad tracks) but there is no signage anywhere to guide you. So when we got to the end, we turned around & headed in the other direction (south). THIS NORWSTTUCK TRAIL definitely needs some help. (Or maybe some day to be extended.)
Back to where we started out & this time heading in the other direction the trail actually becomes nice & very well marked. It seems to become the NEWHAVEN AND NORTH CANAL RAIL TRAIL (BUT there are no signs to this effect).
Where you meet the MANHAN RAIL TRAIL the signage is very clear, even as you are going through a village center or crossing a street or road, & the trail is very nice. You're following the reservoir & get some nice riding in.
We just kept going until we reached Easthampton. There you can even pick up trail maps! Ride on, and by the Municipal Bldg there's a nice park & large pond where you can see Mt. Tom behind it. Lovely, relaxing, scenic.
Then the ride back to Northampton but this time we knew the trail well & just enjoyed it.
North of Ferry St., at Lower Mill Pond, the Manhan Trail branches off and follows the river, eventually reaching the Connecticut River & Mt. Tom State Reservation. Should be a lovely ride! (You can also turn off here when you're riding south from Northampton.
We are casual cyclists (no ebikes) and decided to take a short ride on this trail. We parked at the Nassau Lake Trailhead which has about 13 parking spots. We headed towards East Greenbush and cycled about 8 miles before turning around. The 8 mile section of the trail we cycled was paved and very well maintained. There was a slight elevation gain in this section but made for a nice downhill on the way back. There were no amenities on the 8 mile route. The trail had a couple of easy street crossings but was mostly off-road.
On the way back, we continued pass the TH parking for about 3 miles to the Village of Nassau to have a look. There is another TH in town next to a small park and across the street from an ice cream shop. This section of the trail in the village was flat. If we had the time, we would have gone further.
I would recommend this trail.
Wonderful trail. Part of the larger Empire State Trailway. This part from Eastview to Baldwin Place is the section I ride the most. Mostly shaded once you're north of Millwood with plenty of spots where you can stop for a bite or veer off for road riding near the reservoirs.
The trail is not accessible for a 3-mile stretch. From Green Haven and then Eastbound is impossible to pass. Trees have fallen down virtually every 50 yards blocking passage. I carried my bike past about 6 trees and each time I saw another tree blocking the trail. I came across a clean up crew that told me the downed trees went all the way to Green Haven. I was 3 miles east of Green Haven when the mess started. There is also debris along the entire section which I was fortunate not to get a flat tire. The cleaning crew told me they have only 4 people and they will try to hire a contractor to clear the trees. There is no way a crew of 4 people could handle this. It would take them months to clean it up. (July 10, 2026)
I disagree with the description that this trail is packed enough for skinny road tires. There are parts with thicker gravel and I was glad to have gravel tires on my bike and even then it was a bumpy ride. Nice scenery, not too crowded, good bathrooms. Overall loved it.
The Trailways Bridge over the river in Brewster is open, eliminating the on-road detour. The eastern end is currently at the NY/CT line at Farrington Woods (with trail parking) in CT. Long range plans are to develop the CT portion of the RR path to Danbury.
There are far more legit parking areas than currently shown on TrailLink. Services are few and some might seem close lack easy access from route to road. High point is Whaley Lake. The trail is in good condition for it's entire length.
Great ride. First time on a gravel surface and found it pretty easy going with a few rough spots. It rained the night before and early morning, so I wasn’t sure what to expect. Trail was damp but no big puddles. I took in 28 miles of the 40 out and back. Will do it again and try to get the whole distance.
Rode Simsbury down to Plainville. Simsbury to Avon was full of tree root bumps, and lots of branches & trail debris. It's almost as if Simsbury wants to keep cyclists out. ¿ However, Avon and Farmington were great rides, as was Plainville.
Quiet, peaceful, looking for a different perspective in life, these trails will definitely will. The Red trail leads to the science parts of the Hudson. The blue trail goes all around the large pond which is also beautiful.
Rode from Avon, CT to Westfield, MA. Mass section in great shape. CT section is awful. Pavement is split, constant 'ka-thunk', pot holes not marked, just horrendous condition. Where is the CT DOT and our tax dollars? Stay away.
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