Stamford, NY Walking Trails and Maps

396 Reviews

Looking for the best Walking trails around Stamford?

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

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Activities
Length
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Type
22 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

Andes Rail Trail

4 mi
State: NY
Dirt, Grass

Ashokan Rail Trail

11.5 mi
State: NY
Crushed Stone

Ashokan Reservoir Promenade

2.7 mi
State: NY
Asphalt

Erie Canalway Trail

335.2 mi
State: NY
Asphalt, Concrete, Crushed Stone

Parksville Rail Trail

1.3 mi
State: NY
Cinder

Wallkill Valley Rail Trail

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

Catskill Scenic Trail

26 mi
State: NY
Cinder, Crushed Stone, Dirt, Gravel

Kaaterskill Rail Trail

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

Kingston Point Rail Trail

2.15 mi
State: NY
Asphalt

O&W Rail Trail (Ulster County)

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

Liberty Rail Trail

2.4 mi
State: NY
Asphalt, Cinder, Dirt, Grass, Gravel

O&W Trail (PA)

32 mi
State: PA
Dirt, Gravel

Sullivan O&W Rail Trail

20.65 mi
State: NY
Asphalt, Grass, Gravel

Chenango Greenway River Trail (South)

4.6 mi
State: NY
Crushed Stone, Dirt, Grass

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
Accordion

Hunter Regional Trail

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

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 Andes Rail Trail begins in the quaint town of Andes in the beautiful Catskill Mountains region of southeastern New York and follows a branch of the former Delaware and Northern Railroad. At the...
NY 4 mi Dirt, Grass
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
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
The Parksville Rail Trail is the northernmost section 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...
NY 1.3 mi Cinder
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 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 Catskill Scenic Trails runs for 25.6 miles between Bloomville and Roxbury, winding through a broad farming valley and small towns in New York’s Catskill Mountains. The West Branch of the Delaware...
NY 26 mi Cinder, Crushed Stone, Dirt, Gravel
The Fonda, Johnstown & Gloversville Rail-Trail (FJ&G) has one main section and one shorter section. The main segment runs for nearly 8 miles between Union Avenue in Johnstown and the intersection of...
NY 10.5 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
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 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 Liberty 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 2.4 mi Asphalt, Cinder, Dirt, Grass, Gravel
The O&W Trail (PA) stretches 32 miles throughout northeastern Pennsylvania. About the Route There are two trails named the O&W: one in New York and this one in Pennsylvania. Although the...
PA 32 mi Dirt, Gravel
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
The Chenango Greenway River Trail (South) provides a scenic, multi-use trail system along the Chenango River, perfect for walking, running, and biking. It is a 4.6-mile route that is well-suited for...
NY 4.6 mi Crushed Stone, Dirt, Grass
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
Accordion
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
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

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 !!

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.

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!

Wallkill Valley Rail Trail

worth the time & effort

October, 2024 by kaiser

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

O&W Rail Trail (Ulster County)

O&W Kingston

September, 2024 by kaiser

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

Albany-Hudson Electric Trail

Nassau to Stuyvesant Falls Park

August, 2024 by andrix

This trail (14 mile section) was in pristine condition with surprising amount of wildlife (herons, deer, turtles) along the way. Park, falls and 1800's mill factory at the southern end was worth a stop. Maybe shaded 50% so suntan lotion a must. There's a parking lot in Nassau right next to the trail. As others have mentioned, very few bathroom facilities on route.

Sullivan O&W Rail Trail

overgrown, unmaintained

August, 2024 by mwoods54321

I tried this trail starting in two spots. First at the north end off 208. The first few hundred yards are good, but then it becomes overgrown. I went through the brush and mud for another few hundred yards, but turned around at a washed out culvert. Next I drove to the north end of the southern section off S road. This was better. Bumpy with roots across the trail. Foot tall grass in most places, but passable for a half mile or so. After the underpass there are several bridges in degrading condition. I didn't dare ride across, but walked these. There were also downed trees in two spots. A little over a mile in I turned around at another rotting bridge that had 3 large snakes (I believe Northern Water Snakes, but not 100% sure).
I wouldn't waste your time with trying this trail.

Ashokan Rail Trail

great bike trail

July, 2024 by frednshapiro

This mostly flat, well maintained trail goes though woods and across dykes. The scenery makes this a near perfect trail.

O&W Rail Trail (Ulster County)

Newly paved north end!

July, 2024 by bsmith4_tl

Had a great ride yesterday on the north end going from Kingston trailhead to just before Marbletown wooded trail. Marbletown south was a little muddy from recent rains. Ran into 3 folks on horses there too!

Catskill Scenic Trail

Started in Roxbury and fell a couple of miles short of finishing trail but headed back. A lot of mud towards Bloomfield section.Can't say enough about the views. Totally fine for any gravel bike or hybrid .

July, 2024 by antross73

Started in Roxbury and fell a couple of miles short of finishing trail but headed back. A lot of mud towards Bloomfield section.Can't say enough about the views. Totally fine for any gravel bike or hybrid .

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Accordion

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