Pine Plains, NY Running Trails and Maps

1300 Reviews

Looking for the best Running trails around Pine Plains?

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

  • Relevance
  • Name
  • Length
  • Most Popular
Activities
Length
Surfaces
Type
54 Results
Activities
Length
Surfaces
Type

Albany County Helderberg-Hudson Rail Trail

8.9 mi
State: NY
Asphalt, Crushed Stone

Albany-Hudson Electric Trail

26.6 mi
State: NY
Asphalt, Crushed Stone

Ashokan Rail Trail

11.5 mi
State: NY
Crushed Stone

Ashokan Reservoir Promenade

2.7 mi
State: NY
Asphalt

Ashuwillticook Rail Trail

13.9 mi
State: MA
Asphalt

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Columbia Greenway Rail Trail

3.1 mi
State: MA
Asphalt

Erie Canalway Trail

335.2 mi
State: NY
Asphalt, Concrete, Crushed Stone

Farmington Canal Heritage Trail

48.9 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Concrete, Crushed Stone

Harlem Valley Rail Trail

26.2 mi
State: NY
Asphalt

Hudson Valley Rail Trail

7.1 mi
State: NY
Asphalt

Kennedy Trail

1.7 mi
State: NY
Cinder

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

North County Trailway

20.7 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
Accordion

Sue Grossman Still River Greenway

3.4 mi
State: CT
Asphalt

Walden-Wallkill Rail Trail

4.3 mi
State: NY
Asphalt, Ballast, Cinder, Crushed Stone, Dirt, Grass, Gravel

Walkway Over The Hudson

1.6 mi
State: NY
Concrete

Wallkill Valley Rail Trail

21.4 mi
State: NY
Asphalt, Cinder, Dirt, Gravel

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

D & H Canal Linear Park and Towpath Trail

6.84 mi
State: NY
Ballast, Cinder, Dirt, Grass, Gravel

Jones Point Path

2 mi
State: NY
Asphalt

Kaaterskill Rail Trail

2 mi
State: NY
Concrete, Dirt, Grass, Gravel

Kingston Point Rail Trail

2.15 mi
State: NY
Asphalt

Larkin State Park Trail

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

Mamakating Rail Trail

3.2 mi
State: NY
Ballast, Cinder, Grass, Gravel

Middlebury Greenway

4.5 mi
State: CT
Asphalt

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

O&W Rail Trail (Ulster County)

18 mi
State: NY
Asphalt, Cinder, Crushed Stone, Dirt, Grass

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

River-to-Ridge Trail

4.9 mi
State: NY
Gravel

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

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

Old Mine Railroad Trail

2.2 mi
State: NY
Dirt

Billings Trail

3.3 mi
State: CT
Dirt

Naugatuck River Greenway

7.4 mi
State: CT
Asphalt

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel

Hudson River Brickyard Trail

1.5 mi
State: NY
Asphalt, Woodchips

Hunter Branch Rail Trail

1.5 mi
State: NY
Boardwalk, Crushed Stone, Dirt, Grass

Hunter Regional Trail

6.1 mi
State: NY
Boardwalk, Concrete, Crushed Stone, Dirt, Grass, Gravel

Klara Sauer Trail

1 mi
State: NY
Crushed Stone

Marcus J. Molinaro Northside Line

0.57 mi
State: NY
Asphalt

Midtown Linear Park

0.9 mi
State: NY
Asphalt

Mohansic Trailway

1 mi
State: NY
Boardwalk, Dirt, Gravel
Trail Image Trail Name States Length Surface Rating
Overview Following the route of the former Delaware & Hudson (D&H) Railway, the Albany County Helderberg-Hudson Rail Trail serves as a scenic oasis and community connector for residents living...
NY 8.9 mi Asphalt, Crushed Stone
Overview The Albany-Hudson Electric Trail (AHET) follows a 36-mile course through the former Albany-Hudson Electric Trolley corridor from Hudson to Rensselaer in New York State. There are several...
NY 26.6 mi Asphalt, Crushed Stone
Overview The Ashokan Rail Trail is an 11.5-mile multi-use trail that traces the northern edge of the Ashokan Reservoir, which provides a large proportion of New York City's drinking water. The...
NY 11.5 mi Crushed Stone
Overview With vistas of the Catskill Mountains and a vast blue lake, the Ashokan Reservoir Promenade is a paved pathway that spans just shy of 3 miles along the reservoir's southern...
NY 2.7 mi Asphalt
Overview Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along a 13.7-mile paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
MA 13.9 mi Asphalt
Overview 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...
CT 1.8 mi Asphalt
Overview 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...
MA 3.1 mi Asphalt
Closure Notices: In Palmyra/Wayne County, a portion of the trail is closed between route 21 and Swift Landing Park. In Oneida-Verona, Oneida County, a bridge replacement is taking place at the corner...
NY 335.2 mi Asphalt, Concrete, Crushed Stone
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 48.9 mi Asphalt
Overview 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...
CT 16.5 mi Asphalt, Concrete, Crushed Stone
Overview 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 &...
NY 26.2 mi Asphalt
Overview 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...
NY 7.1 mi Asphalt
The Kennedy Trail begins at Brick Hill Road and ends at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers.  The cinder trail, built on a former rail bed,...
NY 1.7 mi Cinder
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
Overview 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...
NY 28.6 mi Asphalt
Overview 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...
NY 20.7 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
Accordion
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
Overview For family riding and walking, the Tannersville Bike Path offers a 2-mile stretch of graded dirt path starting on Clum Hill Road directly across from Cortina Valley. The opposite end is on...
NY 2 mi Dirt, Gravel
The Walden-Wallkill Rail Trail is built on a former Conrail right-of-way. Conrail and its predecessors, Penn Central, New York Central, and The Wallkill Valley Railway, provided service to farmers...
NY 4.3 mi Asphalt, Ballast, Cinder, Crushed Stone, Dirt, Grass, Gravel
Overview 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...
NY 1.6 mi Concrete
Overview The Wallkill Valley Rail Trail runs 21.4 miles between Kingston and Gardiner through woods, fields, farmland. About the Route The corridor’s current incarnation as a linear park...
NY 21.4 mi Asphalt, Cinder, Dirt, Gravel
Overview 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...
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
Overview The D&H Canal Linear Park and Towpath Trail, situated in Wurtsboro, NY carries trail users for 6.84 miles along the former towpath for the historic Delaware and Hudson Trail. Use of...
NY 6.84 mi Ballast, Cinder, Dirt, Grass, Gravel
The Jones Point Path occupies an abandoned motor vehicle route (old US Route 9W). The path provides bicyclists with a relatively safe bypass to a dangerous section of busy US Route 9W near Bear...
NY 2 mi Asphalt
The Kaaterskill Rail Trail offers a beautiful, wooded route through Haines Falls in eastern New York, nestled in the northern Catskills. It begins at the historical Ulster & Delaware Train Station,...
NY 2 mi Concrete, Dirt, Grass, Gravel
Overview 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...
NY 2.15 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
Overview The Mamakating Rail Trail is part of the Sullivan O&W Trail, which runs for 20.65 miles in Sullivan County in 7 distinct sections along the previous O&W Railroad Main Line and Port Jervis...
NY 3.2 mi Ballast, Cinder, Grass, Gravel
Overview The 4.5-mile 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,...
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
Overview The O&W Rail Trail follows the route of the old NY O&W Railroad (Kingston-Port Jervis Branch) right-of-way for 19.1 miles through Ulster County, NY, between Kingston and Ellenville. The...
NY 18 mi Asphalt, Cinder, Crushed Stone, Dirt, Grass
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, Dirt, Grass
Connecting the Walkill River and Shawangunk Ridge, the aptly named River-to-Ridge Trail, which opened in September 2018, runs from New Paltz to the Mohonk Preserve. Begin at the Carmine Liberta Bridge...
NY 4.9 mi Gravel
The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...
NY 3.8 mi 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
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
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
NY 2.2 mi Dirt
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
CT 3.3 mi Dirt
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
Overview The Sullivan O&W Trail runs for 20.65 miles in Sullivan County in 7 distinct sections along the NY O&W Railroad Main Line and Port Jervis-Kingston Branch rights-of-way. The Sullivan O&W...
NY 20.65 mi Asphalt, Grass, Gravel
Overview 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...
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 Hunter Branch Rail Trail (HBRT) is a recently completed segment of the Hunter Regional Trail (HRT), a network of rail-trails that run along a former railroad corridor in the Town of Hunter,...
NY 1.5 mi Boardwalk, Crushed Stone, Dirt, Grass
The Hunter Regional Trail (HRT) is a network of rail-trails that run along a former railroad corridor in Hunter, NY. Currently, there are 6.1 miles of open trail in the hamlet of Haines Falls, the...
NY 6.1 mi Boardwalk, Concrete, Crushed Stone, Dirt, Grass, Gravel
The Klara Sauer Trail (formerly known as the Beacon Riverside Trail) runs for 1 mile along the Hudson River on the west side of New York's village of Beacon. The trail occupies the same corridor as...
NY 1 mi Crushed Stone
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
Following the former Ulster & Delaware Railroad (U&D) corridor, the Midtown Linear Park is part of the Kingston Greenline. Running through Midtown between Westbrook Lane and Cornell Street, the ADA...
NY 0.9 mi Asphalt
The Mohansic Trailway is a rail-trail providing an important link between the North County Trailway and the Franklin Delano Roosevelt State Park. The trailway occupies a short-lived spur of the New...
NY 1 mi Boardwalk, Dirt, Gravel

Recent Trail Reviews

Southwick Rail Trail

A perfect little trail

April, 2025 by robert.richter89

I rode the entirety of the Southwick Rail Trail coming from the Farmington Canal in CT. The Farmington is in very good condition, the Southwick is in even better condition! There are mile markers every mile, the scenery is very peaceful and the trail is very flat making it an easy ride. I stopped as soon as I hit the Columbia Greenway but it is also a seamless transition to that trail as well.

I didn't notice any places to pull off for food but its a short trail so I don't consider that a negative. The trails that join this one really give you so many options for ride length or to visit the trail towns along the way.

Farmington Canal Heritage Trail

A few signs hold it back from five stars

April, 2025 by robert.richter89

I rode the entire northern section of the Farmington Canal Trail from Plainville into MA on a windy Easter Sunday. The trail itself is fully paved, in very good overall condition (there are a few bumps and cracks but nothing major). Simsbury offers a great stopping off point to get refreshments just a quick turn off from the trail. The scenery changes from light industrial parks, residential, marshes, a little farmland and some nice wooded areas.

I have one complaint that prevents this from being a five star trail. The signage could be better. There are times in the more urban areas that I lost the trail, a quick look at Google Maps got me back on and I never was too lost. There are a few signs that were helpful so just a few more would make this a five star trail.

Harlem Valley Rail Trail

Everything you could ask for

October, 2024 by robert.richter89

I rode the entire 24.7 mile southern portion of the Harlem Valley Rail Trail on a beautiful fall day. The HVRT offers everything you could want from a trail experience: a fully paved surface, mostly flat, beautiful scenery (especially in the Fall) and a perfect mid-point trailhead to grab a bite to eat.

I don't recall seeing any water fountains along the trail although the trailhead in Millerton offers many options for places to eat or resupply. The HVRT offers a myriad of scenery changes from farmland, quiet streams, distant hills to quaint towns. I have ridden many paved rail trails in the past and the HVRT is one of the best with almost no surface imperfections for the entire distance. There are many trailheads along the entire trail giving many distance options. All this adds up to a perfect trail in my opinion!

Accordion

Harlem Valley Rail Trail

trail is complete now but map not updated

October, 2024 by vbergerg_tl

Map is 6 months out of date

Ashuwillticook Rail Trail

Mid-Fall Ride

October, 2024 by willipar

Rode the full trail on a glorious October Saturday. the views were spectacular, peppered with fiery fall leaves. The trail is in incredibly good condition over the whole length. Such a lovely ride.

Wallkill Valley Rail Trail

worth the time & effort

October, 2024 by flywithme_tl

Started 3 miles south of New Paltz & ride all the way to Kingston , plenty of places to eat & drink in New Paltz after that there is a farm brewery on your right going north & a little health food eatery in the middle of nowhere by a campsite on the left going north after that you come to get Rosendsle trestle , the mining caves ( you can feel the cold air mass as you ride by ) Once you get to Kingston you pedal via rroad to the town

River-to-Ridge Trail

no rail trail but doable

October, 2024 by flywithme_tl

Trail is all gravel so be careful ! It starts in the center of town in New Paltz goes into a field of green & a view of a mountain it’s ok but I would not do again .

William R. Steinhaus Dutchess Rail Trail

Hopewell Junction

September, 2024 by flywithme_tl

Went from the Thuway area in Poughkeepsie over the walkway and ride to Hopewell junction .Nice trail well groomed , paved not much to look at but very cool what the volunteers did to the RR depot , signal house and pavilion, the depot museum was great . Went to Daddy O’s restaurant on the trail , good food . The NY empire trail continues along live tracks goes I believe quite far .

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

O&W Rail Trail (Ulster County)

O&W Kingston

September, 2024 by flywithme_tl

Nice trail a must do . From Kingston it’s paved at least 5 -6 miles the rest is easy ride great scenery !

Ashuwillticook Rail Trail

Late summer ride

August, 2024 by mgraska54

Beautiful smooth ride. Recommend for anyone seeking a pleasurable experience.

D & H Canal Linear Park and Towpath Trail

Another disappointing part of the Sullivan County trail network

August, 2024 by eswnyc

Wildly inconsistent and discontinuous trail. Has potential, but I sense it will be many, many years before this will rival the trails on the east side of the Catskills. Skip this and just go to the Heritage Trail in Middletown.

Find Nearby City trails

Accordion

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.