Southbury, CT Inline Skating Trails and Maps

1747 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

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.

Accordion

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

Heritage Trail (NY)

great trail , great maintenance , would recommend

August, 2025 by campinfool

What a wonderful ride , we did a total of 30 miles from Middletown to Chester and back ! Awesome trail wonderful maintenance of the trail!! Would recommend to anyone that wants to ride Loved the many Jonny on the spots and benches along the trail! As well as eating and drinks along the way to buy ! Even a bike repair station on the trail!!!! ¿¿¿¿ Kevin & Pat Bennett

Harlem Valley Rail Trail

Rural trail with outstanding surface

August, 2025 by andrix

Parked at northern end just S of Orphan Farm Rd, NY; Trail surface is outstanding including numerous portions of elevated sections over wetlands. Did not see much in the way of wildlife. Quite rural with the 1st p potty 10 miles south; Turned back at Millerton; Shade 50% or so.

Maybrook Trailway

The Weeds Are Gone

August, 2025 by robertgerry

I just rode the trail today and the weeds mentioned in a previous review have now been mowed and the tree leaning across the trail near Whaley Lake has been cut. The trail is now in excellent condition with none of the typical rail trail root bumps encountered today. BobG.

North Shore Rail Trail

Love the trail, but.............

August, 2025 by pawerfel

Great trail, ride it frequently with my wife. Good workout for 22 miles. Main issue is not the road crossings; we ride many trails with more crossings than this, but on those, the towns take down the brush and you can see cars approaching the intersections. On this trail, you pretty much have to stop and inch out into the road to see these cars, many of whom are not "impressed" by the flashing yellow lights that you need to push a button for. Many drivers are looking at their phones rather than the road these days. You must appraoach these intersections as if you are invisible. Be safe

Maybrook Trailway

Great Ride!

July, 2025 by douglas.klion

A friend and I did this ride today starting from Brewster to Hopewell Junction, continuing on the Dutchess Rail Trail for ~4 miles and back. The ride was excellent, a little over 50 miles with a gradual decent (~10 miles) on the way to Hopewell and ascent back. The trail was very smooth, there were a couple of spots on the Dutchess side that had growth into the trail and one downed tree blocking the way.

Wallkill Valley Rail Trail

great ride!

July, 2025 by v65xtm2gzt

Great ride through the shawingunk mountains ! Trail was great bikes were awesome ! What a beautiful day !!

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