Looking for the best trails around Litchfield?

Explore the best rated trails in Litchfield, CT. Whether you're looking for an easy walking trail or a bike trail like the Walkway Over The Hudson and Windsor River Trail . With more than 62 trails covering 588 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

Windsor River Trail

very nice and clean

November, 2022 by haseenarasool808

It’s beautiful good for kids nice and clean .

Ashuwillticook Rail Trail

Excellent ride- one of the best trails!

November, 2022 by billmeredith58

We rode the Ashuwillticook Trail on 11/07/22 from the Pittsfield trailhead to Adams and back. The ride is excellent, with plenty of scenic highlights along the entire route, smooth paved surface and many places to stop and enjoy. The towns along the route looked inviting enough to divert us, but we had time constraints so we stayed on the route. The head winds on the way back were a challenge..
This is one of the best trails we have been on, not to be missed.
PS Recommend enjoying a long weekend and stayed at a B+B in Lenox...

Note: the restrooms along the route were all closed. I can understand given the time of year but it seemed somewhat premature given the warm weather we had been experiencing.

Wallkill Valley Rail Trail

Great summer ride

November, 2022 by senseibarb

We rented bikes in new paltz to go from there up past Rosendale trestle The rest was closed but that was ok. We past some interesting caves with cold air which was a nice surprise. It is finely crushed gravel which is an up grease from mud; however check your bike company to make sure your tires are appropriate for this type of gravel Definitely picturesque, quiet and peaceful Would highly recommend

Accordion

Harlem Valley Rail Trail

Beautiful scenery along the route but some segments need maintenance

November, 2022 by earth2wayne

The Harlem Valley Trail from Taconic State Park to Wassaic (Metro North Station) spans 24 miles through beautiful farmland and marshy areas with Mountain ranges on both sides (Berkshire and Catskills). The entire trail is paved with asphalt. Unfortunately, there are older segments that sorely need maintenance, especially the roughly 4 mile stretch from Taconic State Park south. The trail is also narrow in spots making it uncomfortably close for bikes traveling in opposing directions. The trail does pass through several towns where you can find places to eat and shop.

Ashuwillticook Rail Trail

Beautiful Trail

October, 2022 by lexonyskiddiecollege

We decided to go when the leaves were just starting to change color and fall. What a great time to go. So many awesome photos we were able to take. The trail is such a relaxing place to enjoy the outdoors. We were only able to do the first section from Crane Ave to the Berkshire Mall entrance. Took us about an hour to leisurely walk that distance before it started to get dark and we had to turn back around. I’m hoping they will decide to put some kind of lighting through out the trail. Otherwise, it’s nice and clean, pet friendly and plenty of spots to rest and take the scenery in and get a few photos. I feel like we will enjoy this trail more now that the crane Ave part is completed.

Ashuwillticook Rail Trail

Beautiful Trail

October, 2022 by lexonyskiddiecollege

We decided to go when the leaves were just starting to change color and fall. What a great time to go. So many awesome photos we were able to take. The trail is such a relaxing place to enjoy the outdoors. We were only able to do the first section from Crane Ave to the Berkshire Mall entrance. Took us about an hour to leisurely walk that distance before it started to get dark and we had to turn back around. I’m hoping they will decide to put some kind of lighting through out the trail. Otherwise, it’s nice and clean, pet friendly and plenty of spots to rest and take the scenery in and get a few photos. I feel like we will enjoy this trail more now that the crane Ave part is completed.

North County Trailway

beautiful & well kept trail!

October, 2022 by 9kw466jjyr

This trail is great despite the middle aged men speeding past you at 90 mph on their LeMonds. I’m not sure if they are bike messengers or just “has beens” trying to live out their dreams of being in the Tour De France, but their speed and shrill shouts of “Left, Left, Left!” piercing the crisp fall air can really ruin what is otherwise a beautiful and relaxing family outing.

Farmington River Trail

very pretty

October, 2022 by lpusztai

We biked from Simsbury to Farmington on the Canal trail. It was nice with the fall color, but there is not much else to see. On the way back we took the River trail. It goes parallel to the river and it is very pretty. It goes thru Canton, which is a charming little town. From there the bike trail is quite good for a while, but then you have to bike on the road. The bike trail sign is painted on the road, but you have to look for it. Traffic was not bad at all. The last part goes thru a simsbury park, there are a lot of roots, gotta be careful. All in all the river trail is very nice, even with a couple of miles of in road biking. there there

Hop River State Park Trail

Wonderful!

October, 2022 by kate.decena

Beautiful for a bike ride in the fall. The trail is well kept, the views are beautiful and is moderately trafficked. I started at the Manchester trailhead and just kept going straight, passing parking lots in Vernon and Bolton. Didn’t notice much options for restrooms or pit stops for food so plan accordingly.

Albany-Hudson Electric Trail

Nice Fall colors

October, 2022 by enlowe12

Just did about 14 miles on this trail. Started in Niverville and headed south to Valatie, then back north to North Chatham and back to Niverville. Surface is very good and well maintained. It is obvious the volunteers who take care of this trail do a great job (thanks, Ron! Just met you today). There is some non-trail surface (sidewalk, shared road) but very little and not much of a distraction from the beauty of the rest of the trail. Well worth a light rain to get wonderful fall color photos.

O&W Rail Trail

Nice ride through the woods

October, 2022 by steve.schwinn

Rode the northern section of the trail yesterday from the parking lot just south of Esopus Creek to the intersection of Lucas Turnpike and Dejager Lane, 13+ miles.
Overall in good condition but definitely not for road bikes due to roots and loose stones in sections. Not easy for cyclocross bikes (like mine) or hybrids.
There are a number of new recently installed informational signs.

Ashuwillticook Rail Trail

Gorgeous fall color ride

October, 2022 by enlowe12

I started at the trail head at Crane ave in Pittsfield and rode the 13+ miles to Adams and back. It is possibly the best trail I have ridden. Paved, well maintained, no roots causing bumps in the pavement. Within 1/4 mile of the start I was out of the industrial area and into wetlands and beautiful scenery. The trail goes along three reservoirs in the 13 miles. There are plenty of places to park and jump on the trail, and also rest rooms along the length. Definitely recommend this trail.

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