Find the top rated hike trails in Plainville, whether you're looking for an easy short hike trail or a long hike trail, you'll find what you're looking for. Click on a hike trail below to find trail descriptions, trail maps, photos, and reviews.
| Trail Image | Trail Name | States | Length | Surface | Rating |
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The Air Line State Park Trail winds 60.3 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is nearly...
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CT | 60.3 mi | Ballast, Crushed Stone, Dirt, Gravel |
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The Bloomfield Greenway Multi-Use Trail currently runs 1.8 miles between Bloomfield and village of Tariffville in the Town of Simsbury. The paved rail-trail passes through woods and fields with...
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CT | 1.8 mi | Asphalt |
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The Branford Trolley Trail is essentially a 0.6-mile footbridge occupying an old bridge along the route of an abandoned trolley track.
About the Route
The long bridge links nature trails on both...
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CT | 0.6 mi | Concrete, Crushed Stone, Gravel |
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The Cheney Rail Trail is a 1.7-mile trail with a crushed stone surface in downtown Manchester.
About the Route
The trail is mostly shaded and a pleasant walk any time of the year. The terrain is...
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CT | 1.7 mi | Crushed Stone |
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The Columbia Greenway Rail Trail offers just over 3 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts.
About the Route
The rail-trail runs between the Westfield...
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MA | 3.1 mi | Asphalt |
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Closure notice: During the week of July 7th, the FCHT will be closed due to repaving from Copperhill Road to the Suffield line and then from RT. 189 to Floydville Rd.
First a canal, then a...
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CT | 49.1 mi | Asphalt |
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A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
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CT | 16.5 mi | Asphalt, Concrete, Crushed Stone |
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The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
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MA | 6.9 mi | Crushed Stone, Dirt, Gravel |
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The Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
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CT | 1 mi | Asphalt |
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Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful 26.2-mile wooded pathway along the former New York & Harlem Railroad...
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NY | 26.2 mi | Asphalt |
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The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
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CT | 1.7 mi | Asphalt |
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It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail trail dive through steep rock cuts...
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CT | 20 mi | Crushed Stone |
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The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
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CT | 3.1 mi | Dirt |
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The Litchfield Community Greenway runs along the former Shepaug Railway railbed in the Town of Litchfield. Operational from 1878 to 1948, the railroad line ran between between Litchfield and...
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CT | 2.5 mi | Boardwalk, Crushed Stone, Dirt |
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The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
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MA | 9.5 mi | Asphalt |
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The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail trail. The Mass Central Rail Trail runs for 36.36 miles from...
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MA | 56.36 mi | Asphalt, Cinder, Crushed Stone, Dirt, Gravel |
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The Maybrook Trailway is a paved multi-use trail stretching across Putnam and Dutchess counties in New York state. The trail, which is owned and was built by Metro North Rail, occupies the former...
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NY | 28.6 mi | Asphalt |
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Note: ALL Trumbull town parks require permit parking stickers year-round (also noted on the signboards at each park entrance).
The Pequonnock River Trail is the formal name for this developing...
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CT | 14.5 mi | Asphalt, Crushed Stone |
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The old New York Central rail line that ran from the Bronx to communities north of the city in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends, tourists...
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NY | 11.8 mi | Asphalt |
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The Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...
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CT | 4.8 mi | Asphalt |
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The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
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CT | 1.3 mi | Asphalt |
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The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
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MA | 1.4 mi | Asphalt |
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The Southwick Rail Trail extends for 6.5 miles between the Westfield town line south and the Massachusetts–Connecticut state line.
About the Route
Along the way, the Southwick Rail Trail travels...
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MA | 6.5 mi | Asphalt |
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Just over 3 miles long, the Sue Grossman Still River Greenway is anchored by Winsted to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck Division of the New York,...
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CT | 3.4 mi | Asphalt |
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The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
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MA | 0.7 mi | Crushed Stone |
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The William R. Steinhaus Dutchess Rail Trail—named for the Dutchess County executive who championed it—is a treasure in New York's Hudson Valley region. The 13.8-mile trail runs through what seems...
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NY | 13.8 mi | Asphalt |
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The Windsor River Trail is a paved trail along the Connecticut River in Windsor Meadows State Park. The trail begins at the state park’s parking lot on E Barber St. The Captain John Bissell Trail,...
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CT | 0.8 mi | Asphalt |
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A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
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CT | 4.4 mi | Asphalt, Concrete |
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The Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...
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CT | 4.5 mi | Asphalt |
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The Charter Oak Greenway offers more than 16 miles of paved pathways through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
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CT | 16.5 mi | Asphalt |
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The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
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MA | 7.8 mi | Asphalt |
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At the turn of the 20th century, Groton & Stonington Railway Company began to move passengers between Groton to Mystic via electric trolleys. But in 25 years, the line had been discontinued due to...
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CT | 1.6 mi | Asphalt, Crushed Stone |
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The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut.
About the Route
Horseback riders use this trail frequently and...
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CT | 10.8 mi | Cinder, Crushed Stone, Dirt, Gravel |
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Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
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CT | 2.9 mi | Asphalt |
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The 4.5-mile Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an...
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CT | 4.5 mi | Asphalt |
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The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
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CT | 5 mi | Asphalt, Crushed Stone, Dirt |
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Bookended by beaches and offering gorgeous vistas of Niantic Bay, the Niantic Bay Boardwalk is a must-do excursion in the small Connecticut village of Niantic, part of the larger Town of East Lyme....
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CT | 1.1 mi | Boardwalk, Concrete, Gravel |
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The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
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CT | 2.1 mi | Asphalt, Gravel |
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The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
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CT | 1.7 mi | Asphalt, Dirt, Grass |
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The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
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MA | 0.9 mi | Asphalt |
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The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
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CT | 1.2 mi | Asphalt, Concrete |
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When complete, Connecticut’s Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
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CT | 4.6 mi | Crushed Stone, Dirt |
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The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.2 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but trail...
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CT | 4.2 mi | Crushed Stone, Dirt |
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Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor...
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CT | 5.4 mi | Asphalt |
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The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
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MA | 0.21 mi | Asphalt |
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Running alongside both the Housatonic and Naugatuck Rivers, the Derby Greenway demonstrates a seamless integration of Connecticut’s natural river systems and parks with man-made interventions of the...
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CT | 1.97 mi | Asphalt, Dirt |
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When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
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CT | 12.2 mi | Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel |
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The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut.
About the Route
The trail passes among suburban acreages, along a creek at one...
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CT | 2.3 mi | Gravel |
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The Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...
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CT | 1.2 mi | Asphalt, Cinder, Crushed Stone |
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Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
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CT | 3.3 mi | Dirt |
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The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short, disconnected segments totaling just over 7 miles.
The...
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CT | 7.4 mi | Asphalt |
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The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...
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CT | 0.75 mi | Asphalt |
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The Fairfield Hills Campus Walking Trails is a 2.1-mile route that encompasses the Newtown Fruit Trail and more.
About the Route
The Fruit Trail is an important endeavor which enriches the...
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CT | 2.1 mi | Asphalt |
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Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
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CT | 2.2 mi | Asphalt |
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Parked at northern end just S of Orphan Farm Rd, NY; Trail surface is outstanding including numerous portions of elevated sections over wetlands. Did not see much in the way of wildlife. Quite rural with the 1st p potty 10 miles south; Turned back at Millerton; Shade 50% or so.
I just rode the trail today and the weeds mentioned in a previous review have now been mowed and the tree leaning across the trail near Whaley Lake has been cut. The trail is now in excellent condition with none of the typical rail trail root bumps encountered today. BobG.
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.
I took a ride on a gravel bike from Putnam to Willimantic and back yesterday. I crossed the bridge in Putnam from Kennedy Drive (a nice paved path there along the north shore of the river!) to pick up the Air Line, which my map app shows as starting there. Though there were some short bits of various trails there, none of them went anywhere. I ended up back on roads and made my way to Town Farm road where the Air Line commenced, with signage. However, the next several miles were very rough, and I would not recommend riding there except with a balloon tire mountain bike with front and back suspension. But from the Pomfret Station on to Willimantic, it was either beautiful, or at least fine, except for some road crossing s with very steep and rocky ramps on both sides. For most riders, those ramps have to be negotiated off the bike. But overall, I had a great experience!
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.
We are stayin at Pine Lake RV resort and wanted to do a paved bike ride. The gravel road reviews made me uncertain. But it was great. Some small inclines but nice ride to the Westville Dam. Very nice destination for a bike ride. Took road back on other side of dam. Much more mountain bike ride but still easy enough. So glad the parking lot was marked well. We almost drove 30 miles for another ride.
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.
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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