Old Saybrook, CT Walking Trails and Maps

894 Reviews

Looking for the best Walking trails around Old Saybrook?

Find the top rated walking trails in Old Saybrook, 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.

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
Type
39 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

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

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Branford Trolley Trail

0.6 mi
State: CT
Concrete, Crushed Stone, Gravel

Farmington Canal Heritage Trail

47.6 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

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt

North Shore Rail Trail

10.4 mi
State: NY
Asphalt

Pequonnock River Trail

13.6 mi
State: CT
Asphalt, Crushed Stone

Quinebaug River Trail

4.8 mi
State: CT
Asphalt

Quinnipiac River Gorge Trail

1.3 mi
State: CT
Asphalt

Washington Secondary Bike Path

19.2 mi
State: RI
Asphalt

William C. O'Neill Bike Path

7.2 mi
State: RI
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

16.6 mi
State: CT
Asphalt
Accordion

Cheney Rail Trail

1.7 mi
State: CT
Crushed Stone

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

Middlebury Greenway

4.5 mi
State: CT
Asphalt

Niantic Bay Boardwalk

1.1 mi
State: CT
Boardwalk, Concrete, Gravel

Putnam River Trail

2 mi
State: CT
Asphalt

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

URI Bike Path

2 mi
State: RI
Asphalt

Derby Greenway

1.97 mi
State: CT
Asphalt, Dirt

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Moosup Valley State Park Trail

5.8 mi
State: CT
Ballast, Crushed Stone, Dirt, Grass, Gravel, Sand

Naugatuck River Greenway

7.4 mi
State: CT
Asphalt

Trolley Trail (CT)

0.75 mi
State: CT
Asphalt

Middletown Westlake Area Bikeway

2.2 mi
State: CT
Asphalt
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
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...
CT 1.8 mi Asphalt
About the Route The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The 0.6-mile bridge links nature trails on both...
CT 0.6 mi Concrete, Crushed Stone, Gravel
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 47.6 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
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...
CT 20 mi Crushed Stone
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
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
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...
CT 13.6 mi Asphalt, Crushed Stone
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...
CT 4.8 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
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...
NY 3.4 mi Asphalt
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
RI 19.2 mi Asphalt
Imagine a wealthy 19th-century textile mill owner building an 8-mile railroad to get coal to his plant or products to market, and then adding accommodations to carry vacationers to beach resorts or...
RI 7.2 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
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...
CT 16.6 mi Asphalt
Accordion
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...
CT 1.7 mi Crushed Stone
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
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...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
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
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 Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...
CT 2 mi Asphalt
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 URI (University of Rhode Island) Bike Path provides a safe conduit for students, faculty and staff to commute to and from school via the William C. O'Neill Bike Path. The asphalt, two-lane path...
RI 2 mi Asphalt
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 you’ll...
CT 4.2 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 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
Closure notice: Moosup Valley State Park Trail is currently closed for renovation. This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from...
CT 5.8 mi Ballast, Crushed Stone, Dirt, Grass, Gravel, Sand
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
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...
CT 0.75 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

Recent Trail Reviews

William C. O'Neill Bike Path

Lovely well managed trail

June, 2024 by andrix

Great ride on a beautiful Saturday mid-June. However, all parking was taken at the Amtrak station area and even at the "Additional Parking" lot. On the other hand there was plenty of parking around the URI campus and the URI bike trail (2 Miles) connects with the O'Neill. The O'Neill trail is mostly shaded, in excellent shape and surprisingly not that crowded. There's numerous road crossings but cars were typically very accommodating to stop. At trails end we went another mile into Narragansett to check out the town and beach scene. All in all a very enjoyable afternoon.

URI Bike Path

University bike trail makes for a nice ride

June, 2024 by andrix

The trail has an excellent surface and made for an easy trip to the University for my wife and I. At the trail end we toured off trail thru the main campus before returning to the William C. O'Neill trail. Total distance of 6 miles. We rated it 4* because of the lack of interesting scenery (other than URI) and being fairly short.

Air Line State Park Trail

Get outta here. Put an asphalt trail down or stop wasting our time.

June, 2024 by db7178

Get outta here. Put an asphalt trail down or stop wasting our time.

Accordion

Hop River State Park Trail

Terrific Trail

May, 2024 by 9q8skpdwwc

Just finished the whole trail, plus the Charter Oak Trail, from Columbia to Manchester, and back. 44 miles at 12.5 mph. A very gentle steady climb of about 500 feet to Bolton Notch, from the east. Also about 500 feet up the South end of Manchester. With the exception of a short stretch leaving Columbia, the trail is very rideable, in fine shape. Highly recommended!

Pequonnock River Trail

Bring your phone with GPS

May, 2024 by sboaters_tl

My wife and I did this trail on touring bikes, starting at Glenwood Park in Bridgeport, and proceeded northward. Easy to follow until Twin Brooks Park where the trail joins the park trails but there is no signage from here northward. Nice surface but we had to stop NUMEROUS times to look at our GPS to determine our location and which trail/path to take. Then finding the Tait Road starting point for the next section was a challenge. Either print out the Trail Description and have a map, and/or have your phone handy as there are very few, if any, signs showing where the trail goes. A nice series of trails once you find them but don't expect ANY directional advice.

North Shore Rail Trail

Relaxed ride for family

May, 2024 by qfranco10

Yes it's along powerlines, but the ride is nice and easy, there are a few places to stop and enjoy a break. Most road crossings have crossing lights.

CTfastrak Multi-Use Trail

Trail starts downtown New Britian, easy to find. Trail was clean, well marked except when you hit the main road for a little distance. Not a lot of people on 5/25/24. There's not a lot to look at but a nice 4.4 Mile trail.

May, 2024 by carlosccalhoun

Trail starts downtown New Britian, easy to find. Trail was clean, well marked except when you hit the main road for a little distance. Not a lot of people on 5/25/24. There's not a lot to look at but a nice 4.4 Mile trail.

Farmington Canal Heritage Trail

Farmington/Heritage

May, 2024 by blujeepin76

Over run with cyclists. Many very inconsiderate. They don’t ring their bell until right behind you. Should be a biking speed limit. Many older people can’t move out of the way when there are pairs of cyclists that stay side by side. Extremely inconsiderate. Not all but too many are.

North Shore Rail Trail

Fairly flat

May, 2024 by z4g9gshqpr

Only two things keeping this from being a 5 star are the numerous road crossings and the fact that the trail is under power lines. Best in the area.

Pequonnock River Trail

outstanding!

May, 2024 by iemontejo

Make sure to understand the trail entry points!

Washington Secondary Bike Path

Trash and and dog shit everywhere.

April, 2024 by jtheriault1225

It's a nice path, don't get me wrong, but people are trashy as hell. First of all, if this is labelled as a bike path, don't tell walkers to walk against bikers. Also, there's trash everywhere and dog crap on the actual path. Whoever lived in that area takes this path for granted and it shows. I would be thrilled to have a path like that near me. Pick up after yourselves - JC!

Hartford Riverwalk

peaceful walk

February, 2024 by karencoaletracey

I stopped on Wednesday on my way home to walk my dog. Very quiet during the week and a lovely walk if you like to listen to the water from the Connecticut river flowing by. You can see where the river has flooded, read the various historical statue plaques.

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.