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Milford, Connecticut Trails and Maps

Looking for the best trails around Milford, Connecticut? Find the top rated trails in Milford, 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.
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TRAIL LENGTH SURFACE TRAIL MAP

Air Line State Park Trail

53.6 miles
Air Line State Park Trail winds for 53 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state border, you can make a contiguous connection to the ...
Gravel

Bethpage Bikeway

12.5 miles
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 Woodbury. There are a few parkway exit crossings ...
Asphalt

Branford Trolley Trail

0.5 miles
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 marsh habitat that is home to many shorebirds, ...
Concrete
Crushed Stone
Gravel

Briarcliff-Peekskill Trailway

12 miles
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 orginally acquired in 1929 by the Westchester Parkway ...
Asphalt
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Bronx River Greenway

18.1 miles
The Bronx River Greenway will one day stretch 23 miles along the river through New York's Westchester and Bronx counties. Currently, 18 miles of the trail are complete in disconnected segments largely paralleling the Bronx River Parkway. The ...
Asphalt
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Dirt

CTfastrak Multi-Use Trail

5 miles
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 paved trail is 10 feet wide and separated ...
Asphalt
Concrete

Charter Oak Greenway

9.8 miles
The Charter Oak Greenway is a paved, multi-use trail connecting parks and the Captain John Bissell Greenway in East Hartford with residential and commercial areas. The trail runs for 9.8 miles between Forbes Street in East Hartford and Porter ...
Asphalt

Cheney Rail Trail

1 miles
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 Railroad and it went to the Cheney silk ...
Crushed Stone

Cross Island Parkway Trail

3.1 miles
The Cross Island Parkway Trail closely follows its namesake thoroughfare through northeastern Queens. From its northern end, you will soon enter Little Bay Park, which offers lovely views of the Throgs Neck Bridge and the bay. If you get ...
Asphalt

D & H Canal Park

1 miles
Owned by the County of Orange and maintained by the Orange County Department of Parks, Recreation and Conservation, the D&H Canal Park is a 300-acre park with a one mile section of the Delaware and Hudson Canal (1825-1898) and a number of historic ...
Crushed Stone
Dirt
Grass

Derby Greenway

1.85 miles
The Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes across O'Sullivan's Island. One of the centerpieces ...
Asphalt

Farmington Canal Heritage Trail

40 miles
Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles from New Haven to Northampton, Massachusetts. ...
Asphalt
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Farmington River Trail

14.9 miles
The Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A short disconnected section of trail extends between ...
Asphalt
Cinder
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Harlem Valley Rail Trail

17.3 miles
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 being built in segments, and there is still ...
Asphalt
Crushed Stone

Hook Mountain/Nyack Beach Bikeway

4.9 miles
While not a "rail-trail," the Hook Mountain/Nyack Beach Bikeway is a very scenic trail along the Hudson River in Rockland County. The southern half of this trail is flat and runs right along the river at sea level. It is wheelchair accessible ...
Asphalt
Ballast
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Hop River State Park Trail

18.4 miles
Hop River State Park Trail is one of Connecticut's top rail-trails. Narrow cuts and a lush tree canopy make for enjoyable visits year-round. Most of the route, from the Manchester–Vernon town line to Hop River Road, follows a crushed stone surface. ...
Crushed Stone
Dirt
Gravel

Housatonic Rail-Trail in Trumbull (Pequonnock Valley Greenway)

5 miles
The Housatonic Rail-Trail in Trumbull, a.k.a., the Pequonnock Valley Greenway, offers a shady respite from suburban Trumbull, this fairly flat trail overlooks the winding Pequonnock River for much of its 3.4 miles. Rapids and distinctive rock ...
Asphalt
Cinder
Crushed Stone

Housatonic Valley Rail-Trail in Monroe

4.2 miles
The Housatonic Rail-Trail in Monroe is a northern continuation of the Trumbull segment of the rail-trail. Locals refer to it as the Monroe Housatonic Railbed Trail. The 4.3-mile trail is largely forested and is a convenient bike route to William ...
Asphalt
Crushed Stone

Hutchinson River Greenway

2.2 miles
The Hutchinson River Greenway offers a convenient alternative to the Hutchinson River Parkway, which it closely follows. Although adjacent to the busy thoroughfare, trees have been planted along the route to help beautify the path and trail-goers ...
Asphalt
Concrete

Hyde Park Trail

10 miles
The Hyde Park Trail is a 10-mile system connecting national historic sites, town parks and nature preserves in Hyde Park, New York. The trail connects the national historic sites of Vanderbilt Mansion, Home of Franklin D. Roosevelt, and Eleanor ...
Dirt

Jack Harrington White Plains Greenway

1.2 miles
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 Railway right-of-way, extending from a City parking ...
Woodchips

John Kieran Nature Trail

1 miles
The John Kieran Nature Trail is a short loop that borders Van Cortlandt Lake and its associated wetlands. It is a wonderful site for bird-watching. The trail also passes several sites of significance including an old cemetery and the 67-acre ...
Dirt
Gravel
Woodchips

Jones Beach Bikeway (Ellen Farrant Memorial Bikeway)

5.3 miles
Jones Beach Bikeway is a paved bicycle and pedestrian path on the southwestern end of Long Island that parallels Wantagh Parkway from Seaford to Jones Beach State Park. The trail is also known by two other names: Ellen Farrant Memorial Bikeway ...
Asphalt

Jones Point Path

2 miles
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 Mountain, NY. It also serves as a connecting trail ...
Ballast
Dirt

Joseph B. Clarke Rail Trail

2.8 miles
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clarke Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each trail is fairly short but taken together they ...
Asphalt
Crushed Stone
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Kennedy Trail

1.7 miles
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 City, is home to an IBM campus and Pepsi headquarters. The ...
Cinder

Kings Park Hike & Bike Trail

1.5 miles
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 abandoned railroad corridor that was once an old ...
Asphalt

Kress Family Trail

2.5 miles
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in winter, while hikers enjoy the trail during the ...
Dirt

Larkin State Park Trail

10.4 miles
Canopied with deciduous trees for most of its 10.4 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse residential development. Its railroad past began ...
Cinder
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Maybrook Trailway

3.7 miles
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of the Beacon Line, a two part railroad from ...
Asphalt

Middlebury Greenway

4.4 miles
The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an off-road option for running errands and welcomes ...
Asphalt

Mosholu-Pelham Greenway

10.3 miles
The Mosholu-Pelham Greenway connects several parks and recreational opportunities in New York City's north and central Bronx neighborhoods. A portion of the trail is also part of the growing East Coast Greenway, which will span 15 states from ...
Asphalt

Naugatuck River Greenway (Beacon Falls)

0.3 miles
The Naugatuck River Greenway segment in Beacon Falls offers a short, but scenic route along the river that is paved and well-lighted. Just north of the trail's end at the Depot Street Bridge, lies Volunteer Park, a pleasant place to stop and ...
Asphalt

North County Trailway

22.1 miles
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 freight service between New York City and Brewster, ...
Asphalt

Norwalk River Valley Trail

4.3 miles
When completed, the Norwalk River Vally Trail will run from Long Island Sound to Danbury, about 27 miles. To date, disjointed sections are complete in Norwalk and Wilton.
Asphalt

Ocean Parkway Coastal Greenway

3.6 miles
Ocean Parkway Coastal Greenway, which opened in June 2014, runs just shy of 4 miles between Jones Beach State Park and Tobay Beach. Both beaches permit swimming and provide opportunities to purchase food and refreshments. The paved trail ...
Asphalt

Old Croton Aqueduct Trail

26.1 miles
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has been designated a National Historic Landmark. ...
Asphalt
Concrete
Dirt

Old Erie Path

3 miles
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each trail is fairly short but taken together they ...
Ballast
Crushed Stone
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Old Mine Railroad Trail

2.2 miles
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 expanded to include almost 10,000 acres of ...
Dirt

Old Putnam Trail

1.25 miles
Splayed over 1,146 acres in northwest Bronx, Van Cortlandt Park has a lot going on. The park is New York City's fourth largest and is home to the oldest municipal golf course in America. There are playgrounds, walking trails, running tracks, ...
Cinder
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Putnam Trailway

11 miles
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" carried commuters from New York City north to Brewster, ...
Asphalt

Quarry Trail

0.1 miles
The Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic Park and Hastings-on-Hudson trails. Access ...
Dirt
Grass

Ramapo River Trailway

1.88 miles
This project will convert an abandoned railroad spur from the New York State/New Jersey line to an existing bike/pedestrian trail along the Ramapo River as part of a larger trailway system. The trail corridor is located in the western end ...
Asphalt

Raymond G. Esposito Trail

1 miles
These three contiguous trails—the Raymond G. Esposito Memorial Trail, Old Erie Path and Joseph B. Clark Trail—occupy the former right-of-way of the Erie Railroad's Nyack and Piermont Branch. Each trail is fairly short but taken together they ...
Crushed Stone
Dirt
Gravel

Ridgefield Rail Trail

2.3 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 of the town's parks and open spaces, including ...
Gravel

Samuel G. Fisher Mount Ivy Environmental Park

2 miles
A former right-of-way of the NY & NJ Railroad. Near historical Mount Ivy which was the center of a Quaker settlement in the 18th century. Hiking along railroad bed and wildlife observation and wetland ecology.
Ballast
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Woodchips

Savin Rock Trail

1.2 miles
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 end of the trail is anchored by historical ...
Asphalt
Concrete

Shoreline Greenway Trail

2.3 miles
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 trail will connect parks, schools, town ...
Crushed Stone

South County Trailway

14.7 miles
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 Elmsford. Popular with bike commuters seeking relief ...
Asphalt
Concrete

Stratton Brook State Park Trail

1.2 miles
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 park also offers picnic areas, as well as ...
Asphalt
Cinder
Crushed Stone

Sue Grossman Still River Greenway

2.9 miles
The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New York, New Haven, and Hartford Railroad's Naugatuck ...
Asphalt

Tallman Mountain State Park Bike Path

2.1 miles
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 downtown Piermont, New York. The park itself is ...
Asphalt
Cinder
Dirt

Timp-Torne Trail

6.5 miles
Just an hour north of New York City, the Timp-Torne Trail offers a scenic hike through Bear Mountain and Harriman State Parks with panoramic vistas of the Hudson River. The rugged blue-blazed trail travels along Dunderberg Mountain, The Timp ...
Dirt

William R. Steinhaus Dutchess County Rail Trail

13 miles
The 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 landscape of dense tree cover, linking Poughkeepsie at the Hudson River ...
Asphalt