Looking for the best trails around Plainville?

Explore the best rated trails in Plainville, CT, whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Niantic Bay Boardwalk . With more than 53 trails covering 460 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

Harlem Valley Rail Trail

Everything you could ask for

October, 2024 by robert.richter89

I rode the entire 24.7 mile southern portion of the Harlem Valley Rail Trail on a beautiful fall day. The HVRT offers everything you could want from a trail experience: a fully paved surface, mostly flat, beautiful scenery (especially in the Fall) and a perfect mid-point trailhead to grab a bite to eat.

I don't recall seeing any water fountains along the trail although the trailhead in Millerton offers many options for places to eat or resupply. The HVRT offers a myriad of scenery changes from farmland, quiet streams, distant hills to quaint towns. I have ridden many paved rail trails in the past and the HVRT is one of the best with almost no surface imperfections for the entire distance. There are many trailheads along the entire trail giving many distance options. All this adds up to a perfect trail in my opinion!

Harlem Valley Rail Trail

trail is complete now but map not updated

October, 2024 by vbergerg_tl

Map is 6 months out of date

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

Accordion

Cheney Rail Trail

Cheney Trail

September, 2024 by nicoleh742

Hubby and I discovered this trail last fall. We absolutely love it. It's a beautiful hike with all the leaves changing. Great for pets too as it's a pretty flat walk. It's def longer than 1.7 miles though. I love that the leaves are changing we will be frequented this trail alot during this fall season!

William R. Steinhaus Dutchess Rail Trail

Hopewell Junction

September, 2024 by flywithme_tl

Went from the Thuway area in Poughkeepsie over the walkway and ride to Hopewell junction .Nice trail well groomed , paved not much to look at but very cool what the volunteers did to the RR depot , signal house and pavilion, the depot museum was great . Went to Daddy O’s restaurant on the trail , good food . The NY empire trail continues along live tracks goes I believe quite far .

Air Line State Park Trail

We had a great ride! 6.6 miles. Beautiful day!

September, 2024 by susanmazur13

We had a great ride! 6.6 miles. Beautiful day!

Mass Central Rail Trail

Weston-Waltham section

September, 2024 by msandman1943_tl

This section (8/2024) is about 5 miles long. It goes through woodland and past leafy backyards, but it runs alongside the towers for a high-tension power line. Trees have been clear-cut about 25 feet on both sides of the trail, so there's no shade along this section. But the trail is wide, very straight, and smoothly paved. It has a few small ups and downs and crosses four or five quiet roads before it comes to a traffic signal at the intersection of Routes 126 and 27. Just beyond, the trail turns to crushed stone with a few sandy patches. There's a large supermarket and shopping center adjacent to the trail at that point.

Southwick Rail Trail

Very busy on sunny weekend, well kept trail

September, 2024 by mdnkcn

We started going north on Copper Hill Rd East Granby Ct parking area and finished the trail in Westfield MA. Trail was all asphalt and in good shape. Most of the trail was scenic farmland but toward the north end going toward Westfield was some residential and city though still was plesent to the eye. Next time we plan to take the trail south at the Copper Hill Parking and take the trail to where it hopefully meets the Farmington River Trail

Chicopee River Canal Rail Trail

Unfinished trail. Did not feel safe on portions of the trail.

August, 2024 by bdrzyzga

Unfinished trail. Did not feel safe on portions of the trail.

Maybrook Trailway

weeds weeds weeds!!!

August, 2024 by johnjr4

This is a great trail that is now suffering from neglect . The weeds are so overgrown that the trail is almost down to a single lane.

William R. Steinhaus Dutchess Rail Trail

Top Trail

August, 2024 by z4g9gshqpr

Nice and wide. Plenty of room for walkers, runners and bikers alike. Hudson Valley really has a great series of trails and this is one of them. Connects the Walkway Over the Hudson to the Maybrook Trailway. Bikers dream.

Mattabassett Trolley Trail

What's the point....

August, 2024 by jbarrett01

......of having a trail where there is nowhere to park???

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