Greenport, NY Hike Trails and Maps

708 Reviews

Looking for the best Hike trails around Greenport?

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

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Activities
Length
Surfaces
Type
32 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

Farmington Canal Heritage Trail

47.6 mi
State: CT
Asphalt

Hanover Pond Trail

1 mi
State: CT
Asphalt

Hartford Riverwalk

1.7 mi
State: CT
Asphalt

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kings Park Hike & Bike Trail

1.5 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

Quinnipiac River Gorge Trail

1.3 mi
State: CT
Asphalt

William C. O'Neill Bike Path

7.2 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

16.5 mi
State: CT
Asphalt

Cheney Rail Trail

1.7 mi
State: CT
Crushed Stone

EPCAL Alternative Transportation Path

9.28 mi
State: NY
Asphalt

G & S Trolley trail

1.6 mi
State: CT
Asphalt, Crushed Stone

Larkin State Park Trail

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

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt
Accordion

Middlebury Greenway

4.5 mi
State: CT
Asphalt

Niantic Bay Boardwalk

1.1 mi
State: CT
Boardwalk, Concrete, Gravel

Quinnipiac Linear Trail

2.1 mi
State: CT
Asphalt, Gravel

Savin Rock Trail

1.2 mi
State: CT
Asphalt, Concrete

Shoreline Greenway Trail

4.1 mi
State: CT
Crushed Stone, Dirt

URI Bike Path

2 mi
State: RI
Asphalt

Derby Greenway

1.97 mi
State: CT
Asphalt, Dirt

Moosup Valley State Park Trail

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

Parks to Ports Greenway Trail

3.7 mi
State: NY
Asphalt

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 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
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
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
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 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
Overview 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...
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).  Overview  The Pequonnock River Trail is the formal name for this...
CT 14.5 mi Asphalt, Crushed Stone
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
Overview The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore.  Sometimes more simply referred to as the Setauket Greenway, the paved...
NY 3.3 mi Asphalt
Overview 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...
RI 7.2 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
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 Cheney Rail Trail is a 1.7-mile trail with a crushed stone surface in downtown Manchester. About the Route The trail is mostly shaded and a pleasant walk any time of the year....
CT 1.7 mi Crushed Stone
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
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
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
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 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
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 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 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 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
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
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
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 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

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!

Moosup Valley State Park Trail

Horse

August, 2024 by janeyac1

Love the beautiful trail, but horseback riders should have a manure bag on the horses to catch their droppings. Not fair to others walking the trail.

Accordion

Moosup Valley State Park Trail

It’s nice!

August, 2024 by revgil

When I first rode this trail in 2012, it was horrible, even though I had a mountain bike. My wife and I just settled on driving over to Coventry, RI to ride; Moosup was next to impossible. But several months ago work began to get it fixed up. What a nice job, with drainage, a new stone-dust surface, and nice fencing. We have ridden trails all over town country, and this is one of the nicest anywhere. Now, if RI will finish the Washington Secondary Trail from Summit to the state line, I could ride all the way to Providence without having to go on the road!

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???

Moosup Valley State Park Trail

Open again.

August, 2024 by seraph101

There is still some work being done. mostly placing fencing. but, the surface is finished, and the trail is open. Public making use of it again.

Mostly stonedust, with a few paved sections. New signage/crosswalks for road intersections. signs, no blinking lights.

new parking. 3 new lots.
A new parking lot has been added to the corner of Railroad ave and Spring lake rd, just off 14 and 14a in sterling, towards the "end" of the trail, at the ct state line.

A parking lot has been added on industrial park rd, in sterling, up the big field, next to the trail.

Another small parking lot added to Barber hill road, off n main st, across the river next to the trail in Moosup.
the .7m paved section from the start to Barber hill rd is unchanged.


2 park bench locations.
one off Main street in sterling. the north west side, next to Weidele's pizza and pub. (which recently moved from rt 14 to here).
another next to the "rainbow bridge", off the new Babcock rd access.

The project was 3.85million.
Major work done to fix drainage. The vast majority of which does seem solved. Theres a couple places with some problems still. (particularly about .5miles east from rt 14 in sterling, towards babcock/providence rd). some runoff, and one large puddle still.

The bollards blocking the bridge over the moosup river between sterling and moosup, .3 from sterling have been removed. This section is now wheelchair/stroller/bike carriage friendly.

The bollards for the rainbow bridge over Providence road have not been removed. the clearance is 36". (note, the north east side of the trail is only 34". the right side, coming from the paved section. the left side is 36")
plan accordingly.
Bypass is not quick and easy. From moosup, turn up Babcock road access, then right/south onto Providence road, go under the bridge, down to 14A/plainfield pike. Turn left/east on 14a, continue to taking a left onto railroad ave. up to the new Railroad ave trail access.
14a is a fairly heavy use road with little to no shoulder.

The .5mile paved section from Spring lake rd, to the bridge over Providence rd has also been repaired, with pavement.

Official renovations end at 14a, and the state line.

Atvs and dirtbikes are already tearing up the trail... hoping regular foot/bike traffic gets them to stop. not sure who to call, state police, or deep.


The section from RI state border to paved Washington secondary bike path is getting worse.
from ct/ri State line to Lewis farm road its dirt.
heavy use from ATVS/dirt bike is creating moguls and puddles. its still possible to go around, but is getting less fun and manageable every year.
The levee/valley for Carbunkle pond is very soft sand. roadbikes/strollers/wheelchairs beware. get off and walk, and/or try to go on the grass to the north side of the trail. a huge washout at the trail to carbunkle pond.

from lewis farm road, to hopkins hollow rd is railroad grade gravel. perpetually wet. a very large puddle at the entrance of hopkins hollow rd.

from hopkins hollow rd, to log bridge road/summit general store/102. dirt/gravel, and moguls, moguls moguls. past the wind turbines, there is also a large puddle that can be bypassed by going up into the woods.
also a few trees down.

Best to just bypass this section, if on roadbike or all terrain. if coming from Washington secondary, head north up log bridge road, then west on 117. take the right in Green, staying on 117. at Lewis farm road(a dirt road), you have a choice, take it to the trail, and do the slightly rough section between lewis farm rd, and 14a. Or, just stay on 117, continue to 14, taking a left onto it, and continue to 14a, taking a left onto 14a. 14a to the trail again. Renovated section.

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.

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

William C. O'Neill Bike Path

Lovely well managed trail

June, 2024 by andrix

Great ride on a beautiful Saturday mid-June. However, all parking was taken at the Amtrak station area and even at the "Additional Parking" lot. On the other hand there was plenty of parking around the URI campus and the URI bike trail (2 Miles) connects with the O'Neill. The O'Neill trail is mostly shaded, in excellent shape and surprisingly not that crowded. There's numerous road crossings but cars were typically very accommodating to stop. At trails end we went another mile into Narragansett to check out the town and beach scene. All in all a very enjoyable afternoon.

URI Bike Path

University bike trail makes for a nice ride

June, 2024 by andrix

The trail has an excellent surface and made for an easy trip to the University for my wife and I. At the trail end we toured off trail thru the main campus before returning to the William C. O'Neill trail. Total distance of 6 miles. We rated it 4* because of the lack of interesting scenery (other than URI) and being fairly short.

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.

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Accordion

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