Old Saybrook, CT Hike Trails and Maps

911 Reviews

Looking for the best Hike trails around Old Saybrook?

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

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Activities
Length
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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

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

North Shore Rail Trail

10.4 mi
State: NY
Asphalt

Pequonnock River Trail

14.5 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

16.5 mi
State: CT
Asphalt
Accordion

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

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

Moosup Valley State Park Trail

5.8 mi
State: CT
Crushed Stone, Grass, Gravel

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

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
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
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
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
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
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
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
Overview The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. About the Route The rail-trail, Rhode...
RI 19.2 mi Asphalt
Overview 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...
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
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
Accordion
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
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 4.1 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
Overview This 5.8-mile trail runs between Moosup and the Rhode Island/Connecticut border. Wide and flat, this rail-trail is suitable for riders of all levels. The surface is a mix of paved asphalt...
CT 5.8 mi Crushed Stone, Grass, 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
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

smooth and clean

November, 2024 by walkinator007

This is my childhood bike path, it’s a lot shorter than I remembered now that I have the speed and endurance I do. Still a wonderful ride through the swamp and forests of south Kingstown, through peace dale and wakefield , to the beaches of Narragansett.

Washington Secondary Bike Path

Quite the good climb going south

November, 2024 by walkinator007

as of october 2024 this path is paved and quite nice.

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

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!

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

Washington Secondary Bike Path

Trail Construction

September, 2024 by nnnkfpw7zq

The trail in Cranston was repaved recently. There weren’t even lines painted yet! It was a smooth ride. There was one detour due to the paving, but it was an easy ride on a side street.

Moosup Valley State Park Trail

What an improvement!

September, 2024 by bopflu

When I attempted this trail in 2022, I called it "the worst ride of my life." I got covered in mud, and the numerous puddles teemed with mosquitos. But what a difference two years made!

The trail has been vastly improved, now offering a highly pleasant ride through Connecticut's Route 14 corridor. It does, however, become rougher shortly after you cross Route 14-A near the Rhode Island state line. I only hope further improvements will be made.

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!

Moosup Valley State Park Trail

Horse

August, 2024 by janeyac1

Love the beautiful trail, but horseback riders should have a manure bag on the horses to catch their droppings. Not fair to others walking the trail.

Moosup Valley State Park Trail

It’s nice!

August, 2024 by revgil

When I first rode this trail in 2012, it was horrible, even though I had a mountain bike. My wife and I just settled on driving over to Coventry, RI to ride; Moosup was next to impossible. But several months ago work began to get it fixed up. What a nice job, with drainage, a new stone-dust surface, and nice fencing. We have ridden trails all over town country, and this is one of the nicest anywhere. Now, if RI will finish the Washington Secondary Trail from Summit to the state line, I could ride all the way to Providence without having to go on the road!

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???

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