Southbury, CT Inline Skating Trails and Maps

1753 Reviews

Looking for the best Inline Skating trails around Southbury?

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

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Activities
Length
Surfaces
Type
35 Results
Activities
Length
Surfaces
Type

Bethpage Bikeway

13.4 mi
State: NY
Asphalt

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Bronx River Greenway

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

Columbia Greenway Rail Trail

3.1 mi
State: MA
Asphalt

Farmington Canal Heritage Trail

49.1 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

Heritage Trail (NY)

19.4 mi
State: NY
Asphalt, Crushed Stone, Dirt

Hudson Valley Rail Trail

7.1 mi
State: NY
Asphalt

Joseph B. Clarke Rail Trail

4 mi
State: NY
Asphalt

Kings Park Hike & Bike Trail

1.5 mi
State: NY
Asphalt

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

Pequonnock River Trail

14.5 mi
State: CT
Asphalt, Crushed Stone

Putnam Trailway

11.8 mi
State: NY
Asphalt

South County Trailway

14.4 mi
State: NY
Asphalt, Concrete

Southwick Rail Trail

6.5 mi
State: MA
Asphalt

Sue Grossman Still River Greenway

3.4 mi
State: CT
Asphalt
Accordion

Walkway Over The Hudson

1.6 mi
State: NY
Concrete

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

Kingston Point Rail Trail

2.15 mi
State: NY
Asphalt

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt

Quinnipiac Linear Trail

2.1 mi
State: CT
Asphalt, Gravel

Derby Greenway

1.97 mi
State: CT
Asphalt, Dirt

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

Naugatuck River Greenway

7.4 mi
State: CT
Asphalt

Hudson River Brickyard Trail

1.5 mi
State: NY
Asphalt, Woodchips

Marcus J. Molinaro Northside Line

0.57 mi
State: NY
Asphalt
Trail Image Trail Name States Length Surface Rating
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 one of three...
NY 13.4 mi Asphalt
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 with...
CT 1.8 mi Asphalt
The Bronx River Greenway runs for 22 miles along the Bronx River, traveling from the mouth of the East River north to the Kensico Dam, providing views of the natural history of the area. Because the...
NY 22 mi Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel
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 the Westfield...
MA 3.1 mi Asphalt
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
CT 49.1 mi Asphalt
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 rail-trail was...
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
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 & Harlem Railroad...
NY 26.2 mi Asphalt
Built on the former Erie Railroad main line, the 15-mile Heritage Trail runs through the small Orange County towns of Goshen, Chester, Monroe, and Harriman. The shaded trail runs through different...
NY 19.4 mi Asphalt, Crushed Stone, Dirt
Offering a picturesque and family-friendly adventure, the Hudson Valley Rail Trail stretches 7.1 miles through hardwood forests, over Black Creek, and under two spectacular stone-arch bridges....
NY 7.1 mi Asphalt
The 4-mile rail-trail passes through three downtowns. The quaint town centers on the Joseph B. Clarke Rail Trail are compact and surrounded by woodlands, sanctuaries, and parks. About the...
NY 4 mi Asphalt
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 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 former...
NY 28.6 mi Asphalt
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 communities in...
NY 20.7 mi Asphalt
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 River Manor...
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).  The Pequonnock River Trail is the formal name for this developing...
CT 14.5 mi Asphalt, Crushed Stone
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, tourists...
NY 11.8 mi Asphalt
The South County Trailway rolls 14.4 miles through one of the most dense parts of greater New York City, though its backcountry route through pocket woodlots, parks, and golf courses and along...
NY 14.4 mi Asphalt, Concrete
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 Trail travels...
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
Accordion
The Walkway Over the Hudson State Historic Park—the longest pedestrian bridge in the world at 1.28 miles—emerges from the trees and over the rooftops of the old riverfront town of Poughkeepsie,...
NY 1.6 mi Concrete
The William R. Steinhaus Dutchess Rail Trail—named for the Dutchess County executive who championed it—is a treasure in New York's Hudson Valley region. The 13.8-mile trail runs through what seems...
NY 13.8 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 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 the journey...
CT 16.5 mi Asphalt
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 65-acre...
NY 9.28 mi Asphalt
The Kingston Point Rail Trail is a paved pathway stretching from Kingston’s midtown to the Rondout Creek waterfront, connecting important points in the community such as Kingston High School, City...
NY 2.15 mi Asphalt
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 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
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 interventions of the...
CT 1.97 mi Asphalt, Dirt
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 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 Fairfield Hills Campus Walking Trails is a 2.1-mile route that encompasses the Newtown Fruit Trail and more. About the Route The Fruit Trail is an important endeavor which enriches the...
CT 2.1 mi Asphalt
The Hudson River Brickyard Trail runs 1.5 miles from North Street to John Street in East Kingston. Located in Sojourner Truth State Park, the trail follows the shoreline and offers scenic views of...
NY 1.5 mi Asphalt, Woodchips
The Marcus J. Molinaro Northside Line is a 0.57 mile dual-track trail that connects trail users between the city and town of Poughkeepsie. While the northern end of the route is still under...
NY 0.57 mi Asphalt

Recent Trail Reviews

Jones Point Path

Bad shape currently!

September, 2025 by bsmith4_tl

Took a ride on this once nice restored short trail yesterday. The state needs to get back in there and do some basic maintenance. The overgrowth of weeds has turned this into barely a single track lane. Many limbs and broken fencing. It's a shame after all the time and money put into it a few years ago.

Old Croton Aqueduct Trail

OCA south end

September, 2025 by kaiser

Interesting ride did it on a hybrid not a bad ride . Rode from Tarrytown to the end south a few places to get a bite and drink however did not see any porta John’s . Some old stone houses , walls some views of the Hudson River a must see Untermyer park & garden area .

Hop River State Park Trail

Truly Amazing

September, 2025 by mtheis.45

Was visiting the area and am so happy I got my gravel bike out to do this trail. As others have mentioned, it is very, very well maintained and quite smooth, enabling fast riding (I rode the entire trail as listed). As a former rail, this trail has nice and gradual elevation changes and has cool features like the tunnels and bridges. I'd highly recommend and hope to be back for another spin soon.

Accordion

Windsor Locks Canal State Park Trail

Nice Biking spot for a 10-ish mile ride

September, 2025 by mtheis.45

Had a great evening bike ride out at the Windsor Locks Canal trail earlier this month (Aug, '25). The trail is paved, and as others have mentioned, it is not super smooth in some areas where the tree roots are pushing the asphalt up but can be navigated pretty easily. I was riding my gravel bike setup with 42mm tires and was able to go quite fast - averaging 15mph on the ride so it really was not that beat up / bad.

The scenery on the river is very nice, and the canal on the other side was also fun - lots of wildlife to see. Would recommend if in the area!

Farmington Canal Heritage Trail

Rode the entire trail…

September, 2025 by willipar

Rode the entire Farmington Canal Heritage Trail as part of a 2 day ride from Northampton to New Haven. What a fabulous experience! So much variety and New England splendor packed into one journey. It was very interesting to see how each of the towns maintained the trail differently. Everything from the paving to the signage changed as you moved from one village to the next. What an amazing treasure!

Columbia Greenway Rail Trail

Beautifully Designed and Maintained

September, 2025 by willipar

A pleasure to ride!

Walkway Over The Hudson

Walkway Courtesy

August, 2025 by wayne7532

Yes Walkway is wonderful, just one problem Cyclist Courtesy.
Have rode and seen a lot of cycling after 60 years, but never the lack of cycle courtesy that takes place on Walkway. Cyclist not letting one know that one is passing on left, or better yet on right, speeding, limit is10 mph. This is not just happing to slower cyclist but also when passing pedestrians. This also applies to the new E Bike presidents.

Hudson Valley Rail Trail

Great connector trail from New Paltz

August, 2025 by ddylla

This is a great paved trail that connects New Paltz to the Walkway Over the Hudson and then to the Dutchess County Rail Trail. Done together, you can ride for well over 60 miles if you want. The Hampton Inn in New Paltz is a great place to stay with the trail starting just across the street. The hotel also provides easy access to the Wallkill Trail.

Heritage Trail (NY)

Nice trail. Poor signage in Goshen

August, 2025 by ddylla

Overall, a very nice paved trail that’s well maintained but very poor connectivity and signage in Goshen. If not for that poor connection, I would have rated this trail five stars. Well worth checking out and hopefully Goshen will improve that stretch in the future.

Governor Cuomo Bridge

Horrible surface, great views

August, 2025 by vbergerg_tl

While all are grateful that bike and pedestrian access were built into the new TZ Bridge, the rough bumpy surface is completely awful. Neither easy on the feet nor pleasant for bikes. I don’t know if it was like this a few years ago or was planned this way, but it’s disappointing.

Air Line State Park Trail

Willimantic to East Hampton - Just AWFUL!

August, 2025 by geminird

The claim of this being a 61 mile trail is very deceptive. Almost 40 miles of this trail is nearly unrideable except for mountain bikes (and even that would be unpleasant). We are experience riders and were on hybrid bikes with wide tires and front suspension. And while our plan was to cycle 40 miles from Willimantic to E. Hampton, we only did the first 10 mile section from Willimantic to James L. Goodwin State Forest.

The trail started out as just OK, but deteriorated in less than 2 miles. After crossing S. Brook Rd, the trail the trail was extremely gnarly and super overgrown. When we reached Goodwin State Forest, we were so happy to bail out and call it quits! Luckily, we had a SAG vehicle with us so we weren't forced to cycle back over the same awful trail.

Be warned, the entire trail we rode from Willimantic to Goodwin Forest was large, loose gravel, and the scenery is incredibly boring. There are places where the trail is extremely rough. At S. Brook Rd. the trail becomes unrideable, expect by maybe some die-hard mountain bikers. We used our SAG van to pop into other points along the trail from Goodwin to E. Hampton the trail only seemed to get even worse.

Honestly, just a really unpleasant ride.

Air Line State Park Trail

A Fabulous, Friendly, and Easy Trail !!!

August, 2025 by pedego2015

We (5) Friends Have Biked This Trail in It’s Sections from E. Hampton to Willimantic for Many Years. We Have Always Considered it to be 4-5 Star Rated, (For a Gravel Trail). Since 2015, We Have Switched to E-Bikes which makes the Trail 3x more FUN !! Having the Best of Both Sun & Shady Sections, It Has Only One small Section of about 300’ Near the Start leaving E.Hampton Where it’s sandy & .Loose

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