Montauk, NY Dog Walking Trails and Maps

399 Reviews

Looking for the best Dog Walking trails around Montauk?

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

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Activities
Length
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Type
14 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

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

Branford Trolley Trail

0.6 mi
State: CT
Concrete, Crushed Stone, Gravel

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

North Shore Rail Trail

10.4 mi
State: NY
Asphalt

Quonset Point Bike Path

2.5 mi
State: RI
Asphalt

Washington Secondary Bike Path

19.2 mi
State: RI
Asphalt

William C. O'Neill Bike Path

7.2 mi
State: RI
Asphalt

EPCAL Alternative Transportation Path

9.28 mi
State: NY
Asphalt

G & S Trolley trail

1.6 mi
State: CT
Asphalt, Crushed Stone

Niantic Bay Boardwalk

1.1 mi
State: CT
Boardwalk, Concrete, Gravel

Shoreline Greenway Trail

4.6 mi
State: CT
Crushed Stone, Dirt

URI Bike Path

2 mi
State: RI
Asphalt

Moosup Valley State Park Trail

5.8 mi
State: CT
Crushed Stone, Grass, Gravel

Trolley Trail (CT)

0.75 mi
State: CT
Asphalt
Trail Image Trail Name States Length Surface Rating
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 is nearly...
CT 60.3 mi Ballast, Crushed Stone, Dirt, Gravel
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 trails on both...
CT 0.6 mi Concrete, Crushed Stone, Gravel
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 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
Beginning from Calf Pasture Point Beach, the Quonset Point Bike Path offers a short-but-sweet path across North Kingstown on Rhode Island's eastern coastline. The 2.5-mile paved pathway is ideal for...
RI 2.5 mi Asphalt
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 Island’s...
RI 19.2 mi Asphalt
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 resorts or...
RI 7.2 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
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
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
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 4.6 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
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 and granular...
CT 5.8 mi Crushed Stone, Grass, Gravel
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

Recent Trail Reviews

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

Air Line State Park Trail

My Ride July 21, 2025

July, 2025 by 9q8skpdwwc

I took a ride on a gravel bike from Putnam to Willimantic and back yesterday. I crossed the bridge in Putnam from Kennedy Drive (a nice paved path there along the north shore of the river!) to pick up the Air Line, which my map app shows as starting there. Though there were some short bits of various trails there, none of them went anywhere. I ended up back on roads and made my way to Town Farm road where the Air Line commenced, with signage. However, the next several miles were very rough, and I would not recommend riding there except with a balloon tire mountain bike with front and back suspension. But from the Pomfret Station on to Willimantic, it was either beautiful, or at least fine, except for some road crossing s with very steep and rocky ramps on both sides. For most riders, those ramps have to be negotiated off the bike. But overall, I had a great experience!

Air Line State Park Trail

Airline Trail Pomfret Ct section

July, 2025 by artzub

July 19 2025
Just rode from Pomfret west to the Rt6 overpass. Most of the trail is good riding except for some rocky sections, but the overgrowth is starting to close off the trail in sections. It is down to just one lane. It would be nice if the state could mow the weeds.

Accordion

EPCAL Alternative Transportation Path

great trail

July, 2025 by peter330

Great trail for riding. No MVs.

Air Line State Park Trail

Beautiful seclusion

June, 2025 by robert.richter89

I rode 20.5 miles of the southern section of the Air Line Trail from East Hampton to Willimantic on a very hot day in June. This section of the Air Line Trail offers gorgeous scenery, peaceful seclusion and a tightly packed gravel surface that is in very good condition throughout. Despite the heat the trail is very shaded which provided much needed relief from the sun. There are a fair amount of road crossings, most are very small, quiet roads and all of the busier roads have warning lights that can be activated to let motorists know you are crossing.

The only two small complaints I have is there is a lack of signage along the trail. There is one very short on road section that I almost missed getting back on the trail due to there being no signage, I just rightly assumed the small unmarked path on the road was the way to get back on the trail. The gates at the road crossings are on the narrow side which can make navigating through the road crossings difficult. I feel these two issues do not at all detract from what this section of the Air Line Trail has to offer.

Hop River State Park Trail

Great place for a ride, scenery, and history

May, 2025 by traillink.qmsck

I recently rode this on a cool day in May from Manchester to Willimantic and back, so right at 40 miles. The trail is well-maintained and foot/bike traffic was light, even though it was a holiday weekend. Very scenic for long stretches and low elevation gain. I rode a gravel bike with 45 mm tires. On a road bike with reasonable tires, this should be do-able (I saw a couple of them), but there is one rough section of about 100ft (30m) where you would need to walk. There is also one underpass that is dark enough to use a headlight...but it's passable if you slow down. There are a number of places to read about the history of the rail line, as well as a few locations with fix-it stations with bike tools and air pumps.
One final tip: Google maps takes you to an intersection on Colonial Road for the Manchester trailhead...the parking lot has a tiny sign that is easy to miss.

Moosup Valley State Park Trail

Great Little Trail!

April, 2025 by 9q8skpdwwc

I rode the Moosup Valley Rail Trail a few days ago from Moosup to Oneco. The trail is in excellent condition all the way, and beautiful! I rode 34mm knobbies, but would have had no trouble on 28 slicks. The only irritants were a guy on a motorized scooter in Moosup and 2 guys on screaming dirt bikes going the other way a bit farther along, but they passed quickly. In Sterling, dirt bikers had dug shallow ruts into a short stretch of path, diagonal to direction of travel, which made it bumpy but not hazardous. Otherwise lovely! I wish Rhode Island would step up to the plate and finish the connector to its Washington Secondary path.

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.

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!

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Accordion

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