Pine Plains, NY Bike Trails and Maps

1310 Reviews

Looking for the best Bike trails around Pine Plains?

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

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Activities
Length
Surfaces
Type
43 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

49.1 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

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

Sue Grossman Still River Greenway

3.4 mi
State: CT
Asphalt
Accordion

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

Jones Point Path

2 mi
State: NY
Asphalt

Kingston Point Rail Trail

2.15 mi
State: NY
Asphalt

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

Norwalk River Valley Trail

12.2 mi
State: CT
Asphalt, Boardwalk, Concrete, Crushed Stone, Gravel

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel

Billings Trail

3.3 mi
State: CT
Dirt

Naugatuck River Greenway

7.4 mi
State: CT
Asphalt

Hudson River Brickyard Trail

1.5 mi
State: NY
Asphalt, Woodchips

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
Trail Image Trail Name States Length Surface Rating
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 southwest of...
NY 8.9 mi Asphalt, Crushed Stone
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 gaps along...
NY 26.6 mi Asphalt, Crushed Stone
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 trail sits on...
NY 11.5 mi Crushed Stone
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 shoreline. About the...
NY 2.7 mi Asphalt
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 the Hoosic...
MA 13.9 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 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
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
Closure notice: During the week of July 7th, the FCHT will be closed due to repaving from Copperhill Road to the Suffield line and then from RT. 189 to Floydville Rd. First a canal, then a...
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
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
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 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 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
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 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
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 Bloomer...
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
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 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 welcomes all...
NY 21.4 mi Asphalt, Cinder, Dirt, Gravel
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 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 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
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, ending at an...
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
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 O&W Rail...
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
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 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
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 Rail Trail...
NY 20.65 mi Asphalt, Grass, Gravel
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
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 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

Recent Trail Reviews

Farmington Canal Heritage Trail

Quick notice: July 7 - 13: Section will be closed

July, 2025 by andrix

Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.

O&W Rail Trail (Ulster County)

a little rough in spots but all in all a great ride !!!

July, 2025 by v65xtm2gzt

Rough in spots but really nice ride !!! Would do it again ! Tough around the steep hill x2 , Tressel bridge !!! But nice scenery and cool breeze Pat and Kevin B

Sullivan O&W Rail Trail

awesome ride

July, 2025 by v65xtm2gzt

Throughly enjoyed the trail end of the trail needs some work otherwise an awesome ride !!!

Accordion

Wallkill Valley Rail Trail

nicest crushed stone trail ever

June, 2025 by vbergerg_tl

Section from New Paltz (and maybe a mile or two below, I haven’t checked) to a mile or so north of the Rosendale Trestle is superb. Just after the Women’s Studio Workshop is an interesting historical furnace chimney. But then the trail comes apart - chunky gravel and hills I wouldn’t want to come down, leading to Williams Lake (saw lots of landscaping going on but no one using that end of it recreationally). I returned to the Women’s Studiovia the road.

Ashuwillticook Rail Trail

Love the scenery. There are plenty of rest areas.

June, 2025 by sicnj2al

Love the scenery. There are plenty of rest areas.

Erie Canalway Trail

rode from Henrietta to lock 33

June, 2025 by tnuhyllek_tl

Beautiful trail. Well maintained. Headed west from Henrietta first, a little secluded. Only went about 2 miles then headed east to lock 33. Felt safer going east. Full of exercise traffic… love to see that!

Ashuwillticook Rail Trail

absolutely lovely

June, 2025 by sfrankovich

I rode this trail from the Northern tip south about 10 miles and back. It was very smooth pavement, a well marked trail and delightful views.

Ashuwillticook Rail Trail

A fantastic trail

June, 2025 by pjohnromeo

Rode it Friday. The views were beautiful, the trail was in great condition, and the road crossings were not a problem at all. I’ll definitely be riding this one again.

Farmington Canal Heritage Trail

Completed through New Haven

June, 2025 by tswetts

I just rode the trail from Cheshire to New Haven Harbor. It gets confusing because of the lack of signage once you go under the Temple St Garage in New Haven. You get dumped out into a street and don't know where to go. The trail is on the road or sidewalk depending on what you prefer. Take a left onto Grove St. continue to the end and take a right onto Olive ST. Follow Olive St. to the end and pick up the trail again on Water St. Cross Brewery ST and take a right to continue on Brewery. Brewery changes to Sargent Drive. Take a left to go under I95 and the water will be in front of you. If you take a right and continue down for a little, along the water's edge, you will find dozens of food trucks to buy lunch before a return trip. It was well worth the trip.

North County Trailway

North county Rail Trail

May, 2025 by kaiser

Entered @ Elmsford and found a parking lot where we unloaded . Well maintained nice scenery along the way as well as a few eateries and gas stations where you can get a drink or snack .

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.

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Accordion

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