Guilford, CT Cross Country Skiing Trails and Maps

960 Reviews

Looking for the best Cross Country Skiing trails around Guilford?

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

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Activities
Length
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Type
24 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

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

Farmington Canal Heritage Trail

47.6 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

Maybrook Trailway

28.6 mi
State: NY
Asphalt

Pequonnock River Trail

14.5 mi
State: CT
Asphalt, Crushed Stone

Putnam Trailway

11.8 mi
State: NY
Asphalt

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Sue Grossman Still River Greenway

3.4 mi
State: CT
Asphalt

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Charter Oak Greenway

16.5 mi
State: CT
Asphalt

EPCAL Alternative Transportation Path

9.28 mi
State: NY
Asphalt

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

Shoreline Greenway Trail

4.1 mi
State: CT
Crushed Stone, Dirt

Derby Greenway

1.97 mi
State: CT
Asphalt, Dirt
Accordion

Norwalk River Valley Trail

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

Ridgefield Rail Trail

2.3 mi
State: CT
Gravel

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

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 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
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
Closure Notice: Due to flooding and storm damage, the Maybrook Trailway from Green Haven Rd. to Depot Hill Rd. See Empire State Trail for more current information. Overview The Maybrook Trailway...
NY 28.6 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
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
Overview The Southwick Rail Trail extends for 6.5 miles between the Westfield town line south and the Massachusetts–Connecticut state line. About the Route Along the way, the Southwick Rail...
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
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
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
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
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
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
Accordion
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
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
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

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!

Southwick Rail Trail

Very busy on sunny weekend, well kept trail

September, 2024 by mdnkcn

We started going north on Copper Hill Rd East Granby Ct parking area and finished the trail in Westfield MA. Trail was all asphalt and in good shape. Most of the trail was scenic farmland but toward the north end going toward Westfield was some residential and city though still was plesent to the eye. Next time we plan to take the trail south at the Copper Hill Parking and take the trail to where it hopefully meets the Farmington River Trail

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.

Accordion

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.

Norwalk River Valley Trail

Two Trails

July, 2024 by z4g9gshqpr

These are really 2 separate trails with a variety of surfaces and a bit of street riding. The Norwalk trail is mostly asphalt going north from the sound while the trail in Wilton has about half going through a wooded area with pea gravel. This is the most enjoyable spot to ride as the other half of the Wilton trail dies out north of town on Route 7 with nothing around. If they were ever able to connect the two routes you would have something.

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.

Maybrook Trailway

beautiful trail with an ownership dispute

July, 2024 by vbergerg_tl

Beautiful needed trail, extending the Dutchess Trail down to Brewster. Pity there seems to be some big ownership/maintenance dispute going on I guess between Dutchess County and NYS? Because right now no one is cutting back the weeds on the Dutchess County side and there’s a big defensively toned sign up saying that Dutchess County is not responsible.

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!

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