Explore the best rated trails in Wolcott, 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 52 trails covering 398 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.
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
The Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at just over 1.6 miles—emerges from the trees and over the rooftops of the old riverfront town of...
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...
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
The Maybrook Trailway is a paved multiuse 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...
The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
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...
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...
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,...
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...
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...
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...
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
The Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill...
The former “Old Put” commuter rail corridor that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties is popular once again, only this time it’s for people riding...
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...
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...
The William R. Steinhaus Dutchess Rail Trail—named for the county executive who championed it—is a local treasure in the Hudson Valley region of New York. The 13.1-mile trail runs through what seems...
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...
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
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 5 miles. The...
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
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...
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....
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...
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,...
The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
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...
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...
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....
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...
The Maybrook Trailway is a paved multiuse 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...
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
The Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
The 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 amusement...
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...
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...
The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...
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....
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
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...
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....
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,...
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...
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
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...
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...
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
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...
The old New York Central rail line that ran from the Bronx to northern bedroom communities in Westchester and Putnam Counties carried commuters during the workweek, but on the weekends tourists...
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
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...
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...
The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...
The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
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...
The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
After many years of driving over an hour from NJ to Turner st in Hopewell Junction to ride the Dutchess trail to Walkway Over the Hudson - it was fun to go south / east in the other direction. I rode about 14.5 miles from Hopewell Junction to Holmes, a mile or so past Whaley Lake. That's roughy half of the Maybrook trailway . 29 miles round trip on a perfect day (7/22/21). As someone noted it is uphill 13 of these 14 miles. But hardly noticeable. Since the locomotives can't manage hills, the railroad builders levelled the right of way. Here with the existing track next to you - you're assured of no steep hills whatsoever. About 65 minutes to the turn around point, very leisurely done but flew back to Hopewell Junction at 17 mph and 40 minutes.
Will explore the other half next week starting in Brewster. I expect it to be just as enjoyable as this was.
I rode this trail out and back on 7/15/2021. Total out and back ride clocked in at 9.55 miles, 150 feet elevation change down heading North, so 150 feet uphill heading back South. I parked in the shopping plaza by the Taco Bell and rode the bike lane to the CTfastrack station where the trail starts.
For the most part the trail was clean except for a broken bottle just outside the first station, and a couple of trash cans that were left out for pickup on one of the sidewalk sections. There were not many people on the actual trail and every single one of them said hello and or thanked me for signaling when passing. The trail parallels not only the bus lane, but also an active train line, Amtrak is doing work on the line so in some places you can smell the new ties that they are installing. On the north end of the trail I stopped at a Dunkin' that was across the street from the station, and at the south end I stopped by the bike shop that is next to the hotel and part of the parking garage. There is a mix of businesses along the trail including convince stores and places to get food. The scenery is a mix of urban, industrial, tree lined, train tracks, and bus depots, if you pay attention you will even see a fiberglass Cobra Shelby along the sidewalk section. You will see plenty of busses, and if you are lucky maybe a train.
I like this trail to walk because it is well paved, flat, no hills, and friendly considerate people especially the bike riders who usually indicate when they are passing me. There is some industrial and kind of dumpy areas that abut the trail unlike where I came from, Woodstock NY, where the paths are pristine and beautiful. However, I like where the trail crosses a bridge across the Mill River just past Veterans Field in Northampton.
This is a great ride for me to test my novice skills. I find myself coming back to here twice a week after work just to get a quick workout in
This is a great trail for biking. Lots of hills so bring your ‘A’ game. You can also rent a bike from Pedego a tenth of mile away from the trailhead. The evoked will get you Thru the hills no problem. Pedego Stony Brook in East Setauket 690 NY 25A.
Okay, I road the whole trail, but on 2 days separated by a month. First I started at the Hopewell Junction parking lot (the end of the William R. Steinhaus Dutchess County Rail Trail). The second time I started riding in Brewster, near the end of the Putnam Valley trail. Either way you are going up a 1-3% grade until the level area near Whaley Lake.
Since it was paved with asphalt last year, this is a very smooth trail. There are several lovely watery areas on this trail and it is a great place for bird watchers. Except for either end, it is a somewhat secluded trail and very quiet. Thank you NYS for your investment.
This is all part of a section of NY's Empire State trail, and includes off road portions in Kingston, NY (the Wallkill Valley Rail Trail - gravel), continues through New Paltz, NY to the Hudson Valley RT, across the Walkway Over The Hudson and then to the Dutchess section. Then it continues through the Maybrook, Putnam, North County and South County rail trails to NYC. So you could ride more than 100 miles paved off-road.
Starting from either end Whaley Lake is the mid-point. From Hopewell Junction you ride east, north, and then south. Views include the Green Haven Correctional facility in Stormville, with its imposing and very high walls, and inmate sounds from inside those walls. From Brewster you ride northward past Ice Pond with its very long straight stretch (one mile?) for time trials. Going this way to the lake is shorter by about 3 or 4 miles than from Hopewell Jct. As you go upward the trail becomes very beautiful with flora and fauna. There are forest areas, beautiful mountain streams, marshlands, swamps, and then Whaley Lake. Also, there are many signs to "Stay on the Trail" to avoid snakes, poison ivy, and ticks, as well as "Stay off the Tracks" or private property.
Great day on the Maybrook. Rode from Lake Tonetta to Hopewell Junction and back, about 44 miles. Having previously ridden from Lake Tonetta to Whaley Lake, I was familiar with the basic trail..gradual uphill from Lake Tonetta to Whaley Lake, gradual downhill then from Whaley Lake to Hopewell Junction. The incline is very gradual, so not super hard but makes for a fairly long pull either way, so keep this in mind. Trail in fine shape. The first part to Whaley Lake passes several nice ponds with some hills in the background. And then Whaley Lake is beautiful, there’s a long stretch right alongside it. From Whaley Lake to Hopewell Junction, the trail is more secluded, passes over a couple of country roads and through rock cuts, and there are a few nice peeks through the trees and a view of the valley. Trail also passes the somewhat harrowing sight of Greenhaven prison briefly and also an area for NYPD canine training with big fences. But I could see this being pretty spectacular in the Fall, and it’s very quiet and peaceful. Hopewell Junction has a great stop at their old train station with picnic tables and restrooms…they did a great job with that. In Hopewell Junction you connect directly to the Dutchess County trail that leads to the walkway over the Hudson. All in all, a really nice trail, good variety of sections and sights. Note that you don’t pass through local downtowns per se, I saw restrooms at the Stormville parking area and at Lake Tonetta and Hopewell Junction. I understand there are a couple of services not far from some of the crossings (e.g. Route 292) but I did not go off the trail on this trip. Definitely worth a visit!
Easy access and very flat and straight. Nice trail to cycle for couples and families.
The trail great the only problem that is happing is that you need to repaint handicap parking areas.
We finished this part of trail on June 18. All paved. The newest section had interesting concrete panels for bridge decks. Good mix of open and wooded areas helpful on 80 degree day. Great Scenery. Very flat. Would suggest some added signage inside state park where road is used. Also at north end of park no signage to indicate how to get to Hillsdale section.
My son and I did a pre-fathers day ride. Trail was terrible. Many dead birds on trail and not well maintained. Would not recommend. No trail markers, or mile markers.
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