Find the top rated trails in Oxford, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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 Pequonnock River Trail is not a name you will see on the ground along this developing trail in southwestern Connecticut. Formalized in 2001 by the state, the regional trail pieced together...
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,...
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
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 Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
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 Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
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...
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
The South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, and...
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...
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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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...
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....
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 William R. Steinhaus Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green...
The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
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...
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...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
The Air Line State Park Trail winds nearly 55 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...
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...
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
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...
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 Locks. Due...
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...
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...
The South County Trailway is a zippy paved trail heading north from Yonkers through the Hudson River Valley communities of Hastings-on-Hudson, Dobbs Ferry, Ardsley, Irvington, Greenburgh, and...
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
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 Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
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 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 North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
The Jack Harrington White Plains Greenway was recently renamed to honor a long-time member of the city's conservation board. The trail's corridor follows the former New York, Westchester & Boston...
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...
The Klara Sauer Trail (formerly known as the Beacon Riverside Trail) runs for 1 mile along the Hudson River on the west side of New York's village of Beacon. The trail occupies the same corridor as...
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 Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
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...
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 Bethpage Bikeway is one of Long Island's most popular trails. It connects Merrick Road in Massapequa with Bethpage State Park, and includes additional trail north to Trail View State Park in...
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
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 Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
The final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...
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 Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
Built in 1888 to link New York and New England to the coal beds of Pennsylvania and the West, the steel cantilever truss Poughkeepsie-Highland Railroad Bridge was the longest bridge in the world for a...
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...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
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 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 William R. Steinhaus Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green...
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...
These three contiguous trailsthe Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trailoccupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each...
Tallman Mountain State Park Bike Path is partially paved and bisects the Tallman Mountain State Park. The route provides a motor-vehicle-free way for bicyclists using US Route 9W to connect with...
Great ride but especially by IBM and where there is an active rusty river flowing there needs to be work done.
My husband and I checked out this trail for the first time on 7/29/2018. It was a Sunday afternoon around 4:30 p.m. and the weather was gorgeous, bright and sunny. The trail has some really beautiful sections and some very secluded sections running through urban neighborhoods. At some points, it was so secluded that it felt like it could be opportunistic for crime. There was literally nobody around, it was kind of eerie. My husband commented that he would not feel comfortable with me riding this trail alone.
The Trail Section approaching the MCC Road called "Great Path" has some extremely large cracks, 4-5 inches. If you're unaware as you approach they are very dangerous.....The Trail from Tolland Turnpike to Burnside Avenue aka Rt 44 is barely ridable because of all the many cracks and bumps. They have gotten worse in the last year....Lastly the trail between Burnside Avenue and Silver Lane, specifically , the first 360 degree curve under the highway has an extremely severe washout. Orange cones have been placed along the edge of the washout, but it is so extreme that someone coming around the blind corner, riding wide in the curve could be severely hurt should they loose control trying to avoid.
These sections of trail needs some serious work, but have not seen any work in years.
After reading some of the reviews I was prepared for a disastrous trail. Yes, its a little bumpy in spots but I felt it was mostly smooth. A couple of places are semi-rough but it wasnt that big of a deal.
Also, getting to it is a little tricky if youre just searching on google for directions. I found the best launch point to be at the northern most end of the South County Trail (just south-east of the Tarrytown Resovior). Drive your car to and get off at exit 23 of the Saw Mill Pkwy. There is a park and ride right there. Park your car and head south on your bike for the South County Trail and North for the North County trail.
From Wassaic to Copake, free parking in Wassaic train lot on weekends. Goes through a few small towns with bike shops including one in Copake. Lots of places to eat in the towns, some country roads tie the rail trails together, a few hills but nothing brutal, beautiful lake, plains, and frams views, and if you don't mind a small hike, check out Bash Bish falls in copake, worth the hike.
I traveled from CT to come try this trail. Started cycling in Hopewell Junction and did the Dutchess trail, then the Walkway Over the Hudson, and the Hudson Valley trail out and back for 36 miles. Took a snack break then went back out to the Walkway and back for a total of 65 miles. Beautiful trail, clean and well kept and super clean bathrooms in Hopewell Junction. Definitely worth the trip. Hope to go back in the fall for autumn colors.
An excellent trail, takes you through mostly wooded areas, so you won't be riding in a blazing sun much. (Take mosquito spray). We started at Baldwin Place, next to New York Sports Club and took north (the trail actually runs both ways, north AND south, from NYSC - but the southern part is probably called differently; whatever the case, the trail map shows NYSC as the south entry point for Putnam Trailway).
If you start of heading north, your ride will be easy and pleasant - you'll spend most of time on a gentle downgrade, almost not touching your pedals. (Which means, of course, it's a harder work getting BACK - so, if you are doing a loop, maybe it's better to start off on the northern end of the trail and then have an easy ride back). The road is asphalt mainly, not in ideal conditions in many places, but nothing overly concerning - I saw people on racing bikes with thin rims. We had our folding and touring bikes, absolutely no issues.
If you are a family with kids, an ideal solution would be to start at the south entry point (NYSC), have an easy glide down, then split and have one of the parents ride back while the remaining party is waiting at one of the parking lots (there are benches in some places, and shops/cafes in others, so it's doable) and then come and pick them up by car.
Dateline: Sunday, July 15, 2018.
Weather: Upper 80's to 90F, very humid.
Starting from north headed south it is a pretty good trail with some very nice scenery, until you reach Millwood. Then it goes from woodland trail to NOISY bike route next to highways. No rail trail surface is perfect and we are very lucky to have off-road paved trails, so I am not going to criticize a few sections of root bumps. It is a worthwhile trail to experience.
I had already done the Putnam County rail trail 2 years ago, which leads right into this one seemlessly. So this time I parked at the northern end in Baldwin Place and went north a bit to find where I turned around last time. I did not intend to do the whole trail for a roundtrip of 44.2 miles, but since I had an energy drink just before starting I kept going. When I got the the SCRT sign, I stopped and looked at my Strava app, which stated I had already done 25+ miles, because I forgot I did about 3 miles on the PCRT before starting on the actual NCRT. So now I figure it will be my first 50-miler! When I got back to my parking area I was SO tired and ready to drop when I realized it would only be about 48+ miles and I needed to go at least another mile north to make 2 more miles for 50. I did it - slowly, but it was not wise to do on such a warm day. I should have waited until autumn and 20 degree cooler temperatures.
I rode the trail last week starting at the Wassaic Metro-North station (free parking only on weekends and holidays) and ending at Orphan Farm Road. I did continue to Hillsdale but as there was no signage to indicate how to find the newest section from Hillsdale to Black Grocery road, I did it on road.
All-in-all, both of the main completed sections are in very good shape, fine for road bikes. For the on road gap I took Route 22 going north (flatter but fairly busy with high-speed traffic) and the Under Mountain Road- Rudd Pond Road Route (hillier but much less traffic with swimming available at Taconic State Park- Rudd Pond) on my return. The roads were in good shape either way.
Bash Bish Falls State Park off the northern section is well worth the minor detour. Stay on the road to the falls parking lot and in a 1/4 mile (up hill) you're in Massachusetts!
Went to the south access point in Warehouse Point and found no parking lot, no sign, and no trail! Drove through the building construction only to find a fence blocking the trail. So I went to the north end in Enfield and that too was blocked with a locked fence. No sign or other way to know it was closed. Hope someone will keep the status updated in the future!
They've just finished paving the trail and it's super. It's the same initial 5K of paved bike path as before, but now it continues down to River Rd and then to Grumman Blvd. You can turn north on Line Rd. to cross the site and complete the loop. 8.75 miles. The paved trail along Grumman Blvd. continues for a ways to the west beyond Line Rd., but then just stops. Perhaps they are planning to make a loop around the whole site? Or maybe they just had extra asphalt.
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