East Haven, CT Walking Trails and Maps

1086 Reviews

Looking for the best Walking trails around East Haven?

Find the top rated walking trails in East Haven, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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Type
51 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

60.3 mi
State: CT
Ballast, Crushed Stone, Dirt, Gravel

Bethpage Bikeway

13.4 mi
State: NY
Asphalt

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Branford Trolley Trail

0.6 mi
State: CT
Concrete, Crushed Stone, Gravel

Bronx River Greenway

24.8 mi
State: NY
Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel

Cheney Rail Trail

1.7 mi
State: CT
Crushed Stone

Farmington Canal Heritage Trail

48.9 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Concrete, Crushed Stone

Hanover Pond Trail

1 mi
State: CT
Asphalt

Hartford Riverwalk

1.7 mi
State: CT
Asphalt

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kennedy Trail

1.7 mi
State: NY
Cinder

Kings Park Hike & Bike Trail

1.5 mi
State: NY
Asphalt

Kress Family Trail

3.1 mi
State: CT
Dirt

Litchfield Community Greenway

2.5 mi
State: CT
Boardwalk, Crushed Stone, Dirt

Maybrook Trailway

28.6 mi
State: NY
Asphalt

North County Trailway

20.7 mi
State: NY
Asphalt

North Shore Rail Trail

10.4 mi
State: NY
Asphalt

Ocean Parkway Coastal Greenway

13.7 mi
State: NY
Asphalt

Pequonnock River Trail

14.5 mi
State: CT
Asphalt, Crushed Stone
Accordion

Putnam Trailway

11.8 mi
State: NY
Asphalt

Quinnipiac River Gorge Trail

1.3 mi
State: CT
Asphalt

Sue Grossman Still River Greenway

3.4 mi
State: CT
Asphalt

Windsor River Trail

0.8 mi
State: CT
Asphalt

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Captain John Bissell Trail

4.5 mi
State: CT
Asphalt

Charter Oak Greenway

16.5 mi
State: CT
Asphalt

EPCAL Alternative Transportation Path

9.28 mi
State: NY
Asphalt

G & S Trolley trail

1.6 mi
State: CT
Asphalt, Crushed Stone

Larkin State Park Trail

10.8 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt

Middlebury Greenway

4.5 mi
State: CT
Asphalt

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

Niantic Bay Boardwalk

1.1 mi
State: CT
Boardwalk, Concrete, Gravel

Quinnipiac Linear Trail

2.1 mi
State: CT
Asphalt, Gravel

Savin Rock Trail

1.2 mi
State: CT
Asphalt, Concrete

Shoreline Greenway Trail

4.1 mi
State: CT
Crushed Stone, Dirt

Derby Greenway

1.97 mi
State: CT
Asphalt, Dirt

Jack Harrington White Plains Greenway

1.2 mi
State: NY
Woodchips

Norwalk River Valley Trail

12.2 mi
State: CT
Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel

Parks to Ports Greenway Trail

3.7 mi
State: NY
Asphalt

Ridgefield Rail Trail

2.3 mi
State: CT
Gravel

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Billings Trail

3.3 mi
State: CT
Dirt

Naugatuck River Greenway

7.4 mi
State: CT
Asphalt

Middletown Westlake Area Bikeway

2.2 mi
State: CT
Asphalt

Mohansic Trailway

1 mi
State: NY
Boardwalk, Dirt, Gravel

Northport Rail Trail

0.75 mi
State: NY
Asphalt, Crushed Stone, Dirt
Trail Image Trail Name States Length Surface Rating
Overview 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...
CT 60.3 mi Ballast, Crushed Stone, Dirt, Gravel
Overview The paved 13.4-mile Bethpage Bikeway runs alongside suburban roads for long segments of the route, but it’s much more than a suburban trail. Each on-road suburban stretch is broken up by...
NY 13.4 mi Asphalt
Overview 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...
CT 1.8 mi Asphalt
Overview 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...
CT 0.6 mi Concrete, Crushed Stone, Gravel
The Bronx River travels from the mouth of the East River north to the Kensico Dam, providing views of the natural history of the area. Because the trail is under development, there are several gaps...
NY 24.8 mi Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel
Overview 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....
CT 1.7 mi Crushed Stone
Overview First a canal, then a railroad, and now a trail defines the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the...
CT 48.9 mi Asphalt
Overview 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...
CT 16.5 mi Asphalt, Concrete, Crushed Stone
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...
CT 1 mi Asphalt
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...
CT 1.7 mi Asphalt
Overview 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...
CT 20 mi Crushed Stone
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers.  The cinder trail, built on a former rail bed,...
NY 1.7 mi Cinder
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...
NY 1.5 mi Asphalt
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...
CT 3.1 mi Dirt
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...
CT 2.5 mi Boardwalk, Crushed Stone, Dirt
Overview 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...
NY 28.6 mi Asphalt
Overview At just over 20 miles, the North County Trailway is the longest of four rail trails created from the former New York Central Railroad’s Putnam Division line. The trail travels through...
NY 20.7 mi Asphalt
Overview The North Shore Rail Trail, formerly known as the Rails to Trails Recreational Path, is a 10.4-mile multi-use recreational path. About the Route From its eastern endpoint on Wading...
NY 10.4 mi Asphalt
Overview The Ocean Parkway Coastal Greenway parallels its namesake roadway 13.7-mile trail on Jones Beach Island, an outer barrier island off the southern coast of Long Island, NY. About the...
NY 13.7 mi Asphalt
Note: ALL Trumbull town parks require permit parking stickers year-round (also noted on the signboards at each park entrance).  Overview  The Pequonnock River Trail is the formal name for this...
CT 14.5 mi Asphalt, Crushed Stone
Accordion
Overview  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,...
NY 11.8 mi Asphalt
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...
CT 1.3 mi Asphalt
Overview The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore.  Sometimes more simply referred to as the Setauket Greenway, the paved...
NY 3.3 mi Asphalt
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,...
CT 3.4 mi Asphalt
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,...
CT 0.8 mi Asphalt
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...
CT 4.4 mi Asphalt, Concrete
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,...
CT 4.5 mi Asphalt
Overview 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...
CT 16.5 mi Asphalt
Overview 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...
NY 9.28 mi Asphalt
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...
CT 1.6 mi Asphalt, Crushed Stone
Overview 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...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
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...
CT 2.9 mi Asphalt
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...
CT 4.5 mi Asphalt
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....
CT 5 mi Asphalt, Crushed Stone, Dirt
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....
CT 1.1 mi Boardwalk, Concrete, Gravel
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...
CT 2.1 mi Asphalt, Gravel
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...
CT 1.2 mi Asphalt, Concrete
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,...
CT 4.1 mi Crushed Stone, Dirt
The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.1 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but you’ll...
CT 4.1 mi Crushed Stone, Dirt
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...
CT 5.4 mi Asphalt
Overview 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...
CT 1.97 mi Asphalt, Dirt
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...
NY 1.2 mi Woodchips
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...
CT 12.2 mi Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel
This shared-use path was built as part of the improvement of NY State Route 347 in Suffolk County. SR 347 is a 15-mile arterial between Hauppauge and Port Jefferson, and the trail is envisioned to...
NY 3.7 mi Asphalt
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...
CT 2.3 mi Gravel
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...
CT 1.2 mi Asphalt, Cinder, Crushed Stone
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...
CT 3.3 mi Dirt
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...
CT 7.4 mi Asphalt
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...
CT 2.2 mi Asphalt
The Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
NY 1 mi Boardwalk, Dirt, Gravel
Overview The Northport Rail Trail runs for 0.75 miles in the suburbs of Northport on Long Island, NY. About the Route The northern end of the Northport Rail Trail is located along Elwood Rd....
NY 0.75 mi Asphalt, Crushed Stone, Dirt

Recent Trail Reviews

Bronx River Greenway

A Bit Disjointed

October, 2024 by cehersh

We attempted to ride the entirety of the greenway in two halves, north and south. North have was pretty good--a lot of raised roots on pavement--from Valhalla and south to Bronxville. The southern half began with an abrupt dead end below Bronxville, followed by miles on road. We eventually linked up with a bike lane alongside roadways that led us as far south as Bronx Zoo. Overall, the trail lack good markings and directives. We were disappointed with the southern section of greenway and aborted plans of continuing to the East River. Wanted to like it!

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!

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

Setauket-Port Jefferson Station Greenway Trail

Great path but the abandoned warehouse is gone so seeing old building aspect gone, and they are not maintaining with the roots pushing up the road

September, 2024 by jrfarrell1991

Great path but the abandoned warehouse is gone so seeing old building aspect gone, and they are not maintaining with the roots pushing up the road

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!

Bethpage Bikeway

Great ride

August, 2024 by f9rys6884g

Biked the entire run, from Woodbury to Massapequa. Completely paved path the entire way. Only half-dozen “small bumps” along the entire way due to tree roots, but seriously, nothing to complain about.

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.

North Shore Rail Trail

great trail

August, 2024 by gatogo4

Easy riding trail. Lots of crossings There are no center posts on some of the crossings making the crossings much easier to navigate. Hope the rest of the center posts could be removed

Mattabassett Trolley Trail

What's the point....

August, 2024 by jbarrett01

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

Maybrook Trailway

5 Star

July, 2024 by z4g9gshqpr

The smoothest trail you will find anywhere around NYC. Nice and long, mostly flat. As others have pointed out, plants are beginning to overgrow on the Dutchess County end and need to be cut back. But the trail goes by numerous lakes and offers fantastic views. Highly recommend. Just make sure to start early because the trail is quite long.

Maybrook Trailway

Maybrook to Brewster

July, 2024 by bktourer1

Excellent trail except for the staircase once you get into Brewster from the Danbury area. Why wasn't a ramp put in instead of 2 steep staircases to carry a bike up or down?

Maybrook Trailway

Incredible Trail -- Almost impassable in Dutchess County Right Now

July, 2024 by dryaun

The Dutchess County portion of this incredible biking trail is almost unusable right now. Weeds wildly overgrown and sticking out 4-5 feet into the trail on either side. The Dutchess County people responsible for this negligence should be ashamed of themselves.

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