These Are the Best Hiking & Biking Trails in Westchester

Ward Pound Ridge Reservation. Photo by Ken Gabrielsen

From secluded paths that skirt gorgeous waterways to trails that bring explorers through some of the county’s most inviting preserves, here is our rundown of the very best hiking and biking Westchester has to offer, along with some top gear, notable landmarks, and a few furry friends you might spy along the way.

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By Paul Adler

Left: Photo courtesy of Westchester County Parks, Right: photo by Frank Roberts

Briarcliff-Peekskill Trailway

One of Westchester’s most popular trails is this 12-mile stretch of verdant parkland that wends its way from Peekskill’s Blue Mountain Reservation all the way to northern Ossining. The land was first acquired in 1929 for the construction of the Briarcliff-Peekskill Parkway, and the trail itself is actually just one element of an extensive system that also includes the North and South County Trailways, as well as the Bronx River Pathway.

Not only does this path make for some mighty peaceful hiking and biking — despite passing through a few backyards and utility areas — it also boasts a surprising number of viewing points and historic structures. Highlights include impressive views of the stone spillway at Croton Gorge Park (inset), a Depression-era fire tower worth a gander near the peak of Mount Spitzenberg, an old bathhouse, a rustic trail lodge, and two historically significant comfort stations constructed by the Civilian Conservation Corps.

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Photo by Edward Crimmins

Bronx River Parkway Reservation

Containing the Bronx River Pathway, The Bronx River Parkway Reservation is Westchester’s oldest park and spans an impressive 807 acres in the southern segment of the county. The reservation was created in 1925 as an adjunct to the Bronx River Parkway and currently consists of three unconnected segments. These include a five-mile section extending from Green Acres Avenue in Hartsdale to Kensico Dam Plaza, a one-mile loop adjacent to Oak Street in Mount Vernon, and what is probably the most attractive stretch: a 4.6-mile section wending from Palmer Road in Bronxville, north to Scarsdale’s Crane Road.

Extending more than 13 miles in Westchester from the New York City line north to Valhalla’s Kensico Dam Plaza, the reservation was one of the first linear parks in the nation and the first official park in the county. Visitors will find intimate ponds, cute wooden footbridges, and hundreds of varieties of native trees and shrubs, making it an ideal spot for hiking, biking, or simply studying nature. To sweeten the deal, on select Sundays in the spring and summer, the Bronx River Parkway is closed to traffic, to encourage bicycling.

High Gear

Get ready to hit the trails in style with some of the top hiking, biking, and camping equipment available in Westchester.

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Nemo Disco 15 Sleeping Bag

Side-sleepers rejoice. This popular bag is a favorite of hikers for its unique spoon shape, which offers increased room at the elbows and thighs, as well as its 650-fill down interior and zippered stash pockets to keep items safe and sound.

$299.95-$319.95; REI, Yonkers

Ibis Ripley LS

Ibis is considered one of the top mountain-bike makers on the planet, and this third-generation carbon-fiber specimen is ideal for Westchester’s unique terrain.

Price Varies; Briarcliff Bike Works, Briarcliff Manor

Women’s Safien Mid GTX Hiking Shoes

These ultra-sharp-looking hiking shoes are big on comfort, with shock-absorbing midsoles and a waterproof exterior, as well as a sleek, molded toecap and GORE-TEX membrane.

$150; The North Face, White Plains

Thermacell Backyard Mosquito Repellant Lamp

For those who want to enjoy their campsite sans mosquitos, try this futuristic lamp, which deters insects with an EPA-registered repellant, rather than frying them alive the old fashioned way.

$21.99; Kelloggs and Lawrence, Katonah

REI Co-Op Camp Dome 2 Tent, National Scenic Trails Print

Bring a little fun into the great outdoors with this two-person backpacking tent, which features a colorful polyester taffeta rainfly and convenient pole-clip design for easy assembly.

$59.93; REI, Yonkers

Photo by Ken Gabrielsen; Hair & Makeup by Charles Anthony and Brittany Evans of salon perri day spa

Ward Pound Ridge Reservation

A whopping 4,315 acres, Ward Pound Ridge Reservation is the county’s largest park and one of its most picturesque. Originally settled by farmers from Connecticut and once a part of Cortlandt Manor, this secluded reservation features several miles of wooded trails, fishing, cross-country skiing, and areas for picnicking and lean-to camping. The land itself comprises sleepy meadows, vernal ponds, wetlands, and sandy moraines. In addition, Stone Hill River and Cross River both run through the park and are home to more than a dozen species of native and stocked fish. Ward Pound Ridge Reservation is also the site of a small nature museum and Delaware Indian center called the Trailside Nature Museum, housed in a structure built during the Great Depression. Keep an eye out for the reservation’s popular landmarks, including the “magic stairs” — a set of unlikely stone outcrops that have been worn away by rainfall — as well as the Leatherman’s cave and rare Native American petroglyphs.

Find Your Hiking Homies!

The Westchester Trails Association

This long-running and widely respected hiking group holds outdoor events every Saturday and Sunday throughout the year. Boasting roughly 250 members, the association is known for including people of various ages and hiking interests, as well as for its astonishingly abundant schedule, with five outings sometimes scheduled for a single weekend!

www.westhike.org

OUTWalking

The LOFT, an active LGBTQ community center located in White Plains, annually holds a wooded walk led by a staff member bringing participants through some of Westchester’s most attractive trails. All ability levels are welcome, and walkers are invited to join, even if they do not want to complete the entire distance.

www.loftgaycenter.org/outwalking

AdobeStock

Half Pint Hikes

These baby-wearing hikes founded by a local mom invite parents along with their infants, toddlers, and children to explore scenic areas in Westchester, as well as Putnam and much of the Northeastern and Western Hudson Valley. Most moms come with babies fastened to their bodies, but little ones can follow along on foot, as well.

www.halfpinthikes.com

The Westchester Hiking Meetup Group

This large group of accepting hikers is specifically tailored to attend to the needs of everyone from slow walkers to nature neophytes. They must be doing something right, since this is one of the largest hiking groups in the entire county and currently boasts an impressive 6,325 members.

www.meetup.com/Westchester-Hiking-Group/

Need a lift? Try renting an electric bike from Sleek eBikes in Tarrytown (www.sleekrides.com). By the way, that spiffy hat is actually a functioning helmet! Photo by Ken Gabrielsen; Hair and makeup by Ashley Lauren Beauty Salon

The RiverWalk

While this 51.5-mile-long series of trails and paths skirting the Hudson River is still a work-in-progress, the RiverWalk already makes for some eminently impressive jaunts. The walk brings visitors on a panoramic voyage through some of Westchester’s most scenic environs, meandering through miles of the Hudson River shore, as well as a number of utterly charming townships. Some of the RiverWalk’s more popular sections include Ossining’s Old Croton Aqueduct, Riverfront Green Park in Peekskill, and stretches that pass through Tarrytown (below), Croton-on-Hudson, and Sleepy Hollow.

Spanning 14 Westchester municipalities, the RiverWalk is part of the Hudson River Valley Greenway system and has been developed through the cooperation of private developers, local governments, and other entities. Currently, 32.9 miles of paved and unpaved paths, esplanades, and sidewalks link dozens of village centers, historic sites, parks, and river-access points. That doesn’t even include roughly 15 miles of pathway still to be cleared, making the RiverWalk an evolving attraction for many years to come.

Trail Map

Map Art by Arlene So

Photo by Bill Winters

Blue Mountain Reservation

Those who enjoy spying the great outdoors atop a bike would have a hard time doing better than Westchester’s expansive Blue Mountain Reservation. At more than 1,500 acres, Blue Mountain Reservation is one of Westchester’s largest parks, boasting a developed forest that includes maple, oak, and beech trees, as well as an extensive network of trails and paths. The northernmost section of Blue Mountain Reservation features freshwater bogs and ponds containing turtles, bullfrogs, and snakes.

Hikes center around the reservation’s two peaks, Mount Spitzenberg and Blue Mountain, which offer incredible views in addition to a combination of challenging and beginner routes totaling more than 20 miles. Highlights include The Sportsman Center, located in Cortlandt, with target ranges; a mountain biking center; and The Blue Mountain Trail Lodge, which is available for rent by groups of up to 20 people and includes camping amenities, such as a kitchen, showers, and dining hall.

The popular Briarcliff-Peekskill Trailway (pg 54) also partially runs through the reservation. While areas around the mountain peaks are reserved strictly for hikers, a sturdy bicycle is perhaps the best way to experience all that the reservation has to offer. Pro-tip: For the very best views, try hitting the rocky promontories on the way up to the peaks.

Camp Site Critters

Keep your eyes peeled for these furry andfeathered denizens of the Westchester woods.
By Brandon Muccitelli

Red-Tailed Hawk

With a wingspan of 45 to 52 inches, the males of this carnivorous species typically soar in circles at high altitudes before diving down and swooping upward in order to attract females. The red-tailed hawk’s natural habitat spans many different biomes, including grasslands, deserts, rainforests, scrublands, and pastures, but in Westchester, you’re most likely to find these rare raptors in central and northern parts of the county, especially around Ward Pound Ridge and the Blue Mountain Reservation.

Coyote

Weighing between 20 lbs and 50 lbs, coyotes form strong family groups. They mate for life and team up to protect their litter and territory. Known as very intelligent animals, coyotes have an omnivorous diet and are known to eat deer, fish, rabbits, rodents, and fruit. These animals can be found throughout the county, but they have been sighted consistently in areas around the South County Trailway.

Bald Eagle

Another majestic bird of prey, bald eagles typically lay between one and three eggs in a typical clutch. While bald eagles will happily scavenge for food, they also actively hunt herring, salmon, birds, amphibians, reptiles, and crabs. Look for these beautiful birds when skirting the Hudson on paths such as RiverWalk or Teatown Lake Reservation.

Black Bear

You might want to pass on cuddling up to this forest-dwelling behemoth that typically weighs 150–300 lbs but can top out in excess of a quarter-ton. An omnivorous species, roughly 300,000 black bears roam the US, but local bears mainly inhabit only the farthest northern reaches of the county.

White-Tailed Deer

Chances are, explorers will spot this graceful forest dweller if they spend enough time wandering the woods of Westchester. White-tailed deer can be found in virtually every park in the county. The populous species is known for its herbivorous diet and surprising swimming ability.

Photo by Hamtech87

South County Trailway

What was once the course of the New York Central Railroad is today one of the most-oft-trod paths in the county. The South County Trailway was developed in two sections, totaling 11.6 miles, and follows the original 14.1-mile path of the railroad through Southern Westchester, from Eastview to the New York City line.

The path, which was completed in 2016, is almost entirely paved, with surprisingly verdant stretches despite passing through a few densely populated areas. You can spy a bit of the trail’s former life at the old Elmsford station, the last remaining train-station structure along the South County Trailway. In addition, history buffs can find markers at most of the former station locations.

Photo by Juan Monroy

North County Trailway

This paved, multiuse path stretches an impressive 22.1 miles from Eastview in Mount Pleasant to Somers’ Baldwin Place, continuing north into Carmel for an additional 12 miles as the Putnam Trailway. The North County Trailway is primarily situated on right-of-way lands that once belonged to the former Putnam Division of the New York Central Railroad and is a continuation of the South County Trailway (pg 60). The northern section of the trail boasts an even greater number of elegant old structures, including the Tudor-revival-style Briarcliff Manor Station, which now serves as a public library, as well as attractive former stations in Railroad Park and Millwood. Like the South Country Trailway, historic marker plaques can be found at several former station locations.

Trail Treasures

Check out these must-see sites, landmarks, and oddities while exploring Westchester’s wealth of natural wonders.

Photo by Charles Stein

Leatherman’s Cave

Ward Pound Ridge Reservation has more than its fair share of notable sites, but the park’s most famous feature is undoubtedly the Leatherman’s Cave. The Leatherman was a wanderer who lived in the late 1800s and wore a suit completely constructed from scraps of his namesake material. The unique individual, and the caves in which he dwelled, predictably make for a host of local folklore.

Photo by Arcoterion

New Croton Dam

Stop by the Old Croton Trail in Croton Gorge Park to experience this breathtaking remnant from the area’s former life as part of a massive — and now defunct — aqueduct system. This stepped dam is undoubtedly one of Westchester’s most impressive architectural landmarks, with its dramatic spillway and eminently serene setting. The aqueduct even boasts its own tree-lined 26.2 mile path, wending its way from Cortlandt to Yonkers as part of the Hudson River Valley Greenway Trail.

Photo by Charles Stein

Bear Rock Petroglyphs

Another gem to be found in the expansive Ward Pound Ridge Reservation, the Bear Rock petroglyphs are an archeological wonder carved several thousands of years ago by native people. The designs carved into this granite boulder are believed to represent a deer, a turkey, and a bear, the primary game of Native Americans from this region.

Photo by Daderot

Lasdon Park Arboretum

While more of a park than a landmark, this stunning arboretum in Katonah deserves a special nod. Some of the most impressive landscaping available to the public in Westchester is on show to anyone who wanders through Lasdon during the spring or summer. Very long hikes or bike rides might not be on the menu here, but if you are looking for a truly beautiful jaunt, it’s difficult to do better.

Photo by Ken Gabrielsen

Marshlands Conservancy

This 147-acre wildlife sanctuary located in Rye is a true favorite of Sound Shore locals and a particularly scenic spot to enjoy a brief jaunt or quick hike. Since the conservancy is located along the Atlantic migratory flyway, curious explorers can easily spot a host of interesting birds and waterfowl. Visitors can also learn about the eye-catching fauna at an on-site nature center. Three miles of unmarked trails pack in an impressive amount of natural splendor, including meadows, marshes, and forestland, as well as a half-mile of shoreline. For those heading to the marshlands from afar, public transportation is available via a one-mile walk from the Harrison train station.