Cheshire, CT Atv Trails and Maps

1004 Reviews

Looking for the best Atv trails around Cheshire?

Find the top rated atv trails in Cheshire, whether you're looking for an easy short atv trail or a long atv trail, you'll find what you're looking for. Click on a atv trail below to find trail descriptions, trail maps, photos, and reviews.

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Recent Trail Reviews

Mattabassett Trolley Trail

Smooth, easy family trail

January, 2021 by michael.parker.md

This was our first family trail with kids that were new to bicycling. Everyone enjoyed the consistent pace of the trail. Not too crowded, but haven't tried middle of summer yet. Takes about 30 minutes to go from one end to the other and back.

Maybrook Trailway

AWESOME TRAIL - completely open

January, 2021 by gjzambetti_tl

This trail is a gem. Fully open now from Tonetta Lake in Brewster to Hopewell Junction. Be aware that there are at least 2 additional parking areas/access points where the trail crosses RT 292 in Holmes (Whalay Lake - Holmes Community Center) and where it crosses Old Rt 55. The trail is in great condition, has some great lake and marsh views throughout and crosses the Appalachian Trail at one point.

Kress Family Trail

Peaceful and only a few people

January, 2021 by jeannecarney21

I visited this beautiful, peaceful trail today for the first time. I started out at 11:45 this Sat and enjoyed every minute. The trail is quite and with relatively few people. Highly recommend!!

Accordion

Bloomfield Greenway Multi-Use Trail

Short and Sweet

November, 2020 by mari-james

Phase 1- the makings of a wonderful trail! Anxiously waiting for the completion of phase 2.

Harlem Valley Rail Trail

one of the very best

November, 2020 by SPanny

I have been riding this trail for years. As of November, 2020, a wonderful new section has just been introduced, stretching from Millerton, NY to Under Mountain Road. This means that the trail now covers almost 24 miles one-way from Wassaic NY all the way to Orphan Farm Road near Copake. This is a classic, beautiful trail the runs through a valley, with so many nice sections: tunnels of trees looking out over farms, places to stop in Amenia and Millerton, a section that runs right to the entrance of Taconic State Park, several raised ridges with views of fields on both sides. The newest area, from Millerton to Under Mountain Road, is perhaps the nicest of all, as it runs through an area with views of the Taconic Berkshires and runs over multiple ponds via the old train bridges (now updated for bicycles). I’ve been on rail trails all over the northeast, this is one of the very best.

Air Line State Park Trail

Disappointed with new trail resurfacing

November, 2020 by carrie.vezina

The Air Line State Park Trail is one of my favorite bike trails in Connecticut. Rode our bikes there last week and was very disappointed with the recently resurfaced section from the Cranberry Bog in East Hampton. The gravel that was used in the resurfacing is to soft and to deep. Has only been open for a week (10/28/2020) and it is already marred by craters from horses and foot traffic. The ride is bumpy like a wash board. At one point I swerved to miss a pile of horse droppings and got to close to the edge which then collapsed under my bike causing me to fall. What was once a favorite section of the trail for us, is now a major disappointment.

Hop River State Park Trail

Nice Trail

November, 2020 by adab

We parked by the pet store mentioned in a previous review and biked to just passed the covered bridge, maybe 6 miles out? Beginning of trail is rough but that ends quickly . Nice ride in the woods. Not much to see. It was a slight incline on the way out which made the return better. I wish there some benches along the way to take a break.

William R. Steinhaus Dutchess Rail Trail

great ride

October, 2020 by jimft13

This trail is an easy ride for everyone. It’s well maintained with plenty of benches to rest and a mixture of sun and shady spots. The end of this trail leads right into the Walkway over the Hudson.

William R. Steinhaus Dutchess Rail Trail

Amazing

October, 2020 by radiggy1

One of the best trails I have done. Nice and smooth. You must do Walkway over The Hudson.

Putnam Trailway

Hilly Section of the Trail

October, 2020 by slipsoup

My friend and I rode from Millwood on the North County Trail and just kept going. We ended up on the Putnam Trailway for a total of 46 miles. There are several decent hills on this segment of the trail. There are some street crossings but they are not very busy roads. You eventually come to the end of the trail, which is clearly marked. Near the end of the trail is a large reservoir. The trail is completely paved with just a few bumpy spots. We rode on 10/10 and the foliage has not changed much yet.

Kennedy Trail

Lovely Easy Trail

October, 2020 by chezbento

Level easy trail quiet and very pretty. Tricky entrance and exit onto busy road. Short easy trail. Wear boots muddy areas.

Pequonnock River Trail

great fall bike trail

October, 2020 by cathmw444

We started at Tait road entrance around 4:30 pm. Path was leafy but dry and good with great views.

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