Windsor Locks, CT Running Trails and Maps

1332 Reviews

Looking for the best Running trails around Windsor Locks?

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

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Activities
Length
Surfaces
Type
57 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

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

Ashuwillticook Rail Trail

13.7 mi
State: MA
Asphalt

Blackstone River Greenway

29.9 mi
State: MA, RI
Asphalt, Boardwalk, Crushed Stone, Dirt

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Branford Trolley Trail

0.6 mi
State: CT
Concrete, Crushed Stone, Gravel

Bridge of Flowers

0.1 mi
State: MA
Concrete

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

3.1 mi
State: MA
Asphalt

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

Harlem Valley Rail Trail

26.2 mi
State: NY
Asphalt

Hartford Riverwalk

1.7 mi
State: CT
Asphalt

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kress Family Trail

3.1 mi
State: CT
Dirt

Litchfield Community Greenway

2.5 mi
State: CT
Boardwalk, Crushed Stone, Dirt

Manhan Rail Trail

9.5 mi
State: MA
Asphalt

Mass Central Rail Trail

59 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt
Accordion

Quinebaug River Trail

4.8 mi
State: CT
Asphalt

Quinebaug Valley Rail Trail

5.7 mi
State: MA
Ballast, Cinder, Dirt, Grass

Quinnipiac River Gorge Trail

1.3 mi
State: CT
Asphalt

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Sue Grossman Still River Greenway

3.4 mi
State: CT
Asphalt

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone

Windsor River Trail

0.8 mi
State: CT
Asphalt

Burrillville Bike Path

1.2 mi
State: RI
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

Cheney Rail Trail

1.7 mi
State: CT
Crushed Stone

Connecticut Riverwalk and Bikeway

5.4 mi
State: MA
Asphalt

Grand Trunk Trail

6.8 mi
State: MA
Crushed Stone, Dirt, Gravel

Larkin State Park Trail

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

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

Putnam River Trail

2 mi
State: CT
Asphalt

Quinnipiac Linear Trail

2.1 mi
State: CT
Asphalt, Gravel

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Rocky Hill Trail

0.9 mi
State: MA
Asphalt

Savin Rock Trail

1.2 mi
State: CT
Asphalt, Concrete

Shoreline Greenway Trail

4.1 mi
State: CT
Crushed Stone, Dirt

Southern New England Trunkline Trail

22 mi
State: MA
Asphalt, Ballast, Crushed Stone

Derby Greenway

1.97 mi
State: CT
Asphalt, Dirt

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Ware River Rail-Trail

15 mi
State: MA
Ballast, Dirt, Grass, Gravel

Moosup Valley State Park Trail

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

Billings Trail

3.3 mi
State: CT
Dirt

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 Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along a 13.7-mile paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
MA 13.7 mi Asphalt
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
MA, RI 29.9 mi Asphalt, Boardwalk, Crushed Stone, Dirt
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
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 Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...
MA 0.1 mi Concrete
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
MA 3.6 mi Asphalt
The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
MA 0.21 mi Asphalt
Overview The Columbia Greenway Rail Trail offers just over 3 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. About the Route The rail-trail runs between...
MA 3.1 mi Asphalt
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
Overview Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful 26.2-mile wooded pathway along the former New York &...
NY 26.2 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
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 Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest,...
MA 9.5 mi Asphalt
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 60 miles from Boston to Northampton...
MA 59 mi Asphalt, 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
Accordion
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 Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
MA 5.7 mi Ballast, Cinder, Dirt, Grass
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 Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
MA 1.4 mi Asphalt
The South Spencer Rail Trail runs for less than 2 miles from downtown Spencer to an area south of town near Spencer State Forest. The path, which is also known as the Depot Trail, occupies a former...
MA 1.62 mi Crushed Stone
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
MA 6.5 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 Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
MA 0.7 mi Crushed Stone
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
Burrillville Bike Path runs for just over a mile through its namesake rural community in northwest Rhode Island. It connects the villages of Pascoag and Harrisville through a corridor that once...
RI 1.2 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
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
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
MA 5.4 mi Asphalt
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
MA 6.8 mi Crushed Stone, Dirt, Gravel
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
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 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 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...
CT 1.7 mi Asphalt, Dirt, Grass
The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
MA 0.9 mi Asphalt
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 Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
MA 22 mi Asphalt, Ballast, Crushed Stone
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
The Ware River Rail-Trail is an unpaved 15-mile rail-trail that stretches between Barre and Baldwinville, running through Hubbardston and Templeton along the way.  Following along the Burnshirt...
MA 15 mi Ballast, Dirt, Grass, Gravel
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
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
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

Charter Oak Greenway

parts are great

July, 2024 by rn28wc7n8y

Manchester towards Hartford is great for a few miles. Then it gets a little dicey and unpleasant. You’re forced onto sidewalks through busy neighborhoods and alongside a highway with only a jersey barrier between you and reckless drivers.

Sue Grossman Still River Greenway

B bear aware

July, 2024 by willthegreat

Twice this week I saw a bear x the trail near the USA transfer station.
Also saw two women digging up poppies! That's a no no!
The extended trail that ends by the motor vehicle bldg has beautiful poppies and other ornamentals! Well done you guys!

Farmington Canal Heritage Trail

love this trail

July, 2024 by pamiller919

The map shows a disconnect, but the trail went all the way through. We did the whole trail and although it had a bunch of twigs it was a great ride. Well marked and in very good condition

Accordion

Ware River Rail-Trail

June 2024 Gravel Bike

June, 2024 by macneilkathy1994

This trail had sand, deep in areas made it not fun for gravel biking.

Blackstone River Greenway

Not a great ride

June, 2024 by pamiller919

Started from India point park and it isn’t marked where to. We lost the “route” many times because of no signage. Very bumpy, wouldn’t call it a scenic ride.

Ware River Rail-Trail

Gates? Trucks on the Trail?

June, 2024 by res3737

I only rode the southern 3 miles of this trail between Route 122 and Route 62. The surface is not bad, no muddy spots, although there was a large pine tree down across the trail that was nearly impassable. My only criticism of this section was that there were no gates at Grange Road or Lackey Lane and I believe only on the southerly side of Covered Bridge Road which meant that I looked over my shoulder at one point to find a Toyota Tacoma bearing down on me. Why are there trucks driving on the rail trail?

Mass Central Rail Trail

MCTR - West Boylston to Rutland

June, 2024 by closey2112

Ok, I recently purchased a ‘24 Trek Checkpoint ALR 5 axs gravel bike. This section of trail is absolutely amazing. Roughly 26.3 miles round trip from West Boylston to Rutland. Starting in West Boylston, Ma you head west. The trail is hard packed dirt. Smoother than most roads in Mass! ¿ No, seriously! Just be careful, this section up to the I-190 bridges, there’s usually a lot of traffic. Especially people with doggos. Some more cognizant than others. But once you cross under the bridges, no dogs are allowed and the traffic thins out. The best section is at the parking lot on Mill St - Holden. It’s packed gravel and as wide a road. It meanders up to the mail Trail and is packed gravel all the way until you hit construction on the trail. So much fun!!!

Ashuwillticook Rail Trail

Nice weather makes the ride nice

June, 2024 by vc2019

Started in Adams and rode to the end and back. Nice weather on this wide paved and shaded trail. It is in great condition. There are a number of road crossings but most are small streets. The gates are all the same, an opening on each side and we saw atleast two recumbent trikes make it through without problems. Photo to show the gates today.

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.

Ashuwillticook Rail Trail

A must ride

June, 2024 by ahanks

Visiting in lower NY area and had this on my bucket list. It was a well paved and maintained trail. Parked at railroad at in Cheshire and rode to the parking area in Pittsfield and then back and a few miles into the Adams area. All in 18 miles. Plenty of options for parking, bathroom Facilities in a few areas and many benches and picnic tables placed to stop and take a break or enjoy the views of the Lindai a or chechsire reservoir. It was well worth the trip!

Columbia Greenway Rail Trail

Enjoyed this trail!

June, 2024 by kdcspamspam

Not too busy, was a little buggy but was nice and pretty smooth. We rollerbladed on it with no issues. Also very pretty scenery!

Rocky Hill Trail

Completely paved; easy

June, 2024 by pianoemily

This was a very short trail which was completely paved. It was nice and shaded due to the trees. It would be an easy walk with grandparents (there are benches) or young children. I recommend setting your gps to find something like 134 Sandy Hill Road in Florence. From there, you can easily find the trail beginning. To get my 10,000 steps I had to go back and forth on the trail a lot. But I still appreciated it fully paved! Seems like more of a neighborhood morning walk trail.

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