Find Your Perfect Hike on These Westchester Trails

Photo by Doug Schneider

Whether you’re an extreme hiker or looking for a jaunt with the kids, you’ll love exploring these top trails around Westchester.

By Paul Adler, with Robert Brum, June Hersh, and Michelle Gillan Larkin

We get it. Some hikers have a few kids (and maybe even a dog or two) in tow, while others are extreme outdoorspeople hankering for that next challenging adventure. Yet others might simply want a nice jaunt with some water views or eye-catching wildlife. Whatever you’re looking for when it comes to alfresco ambulation, you’ll likely find the perfect hike ahead, along with a stellar granola recipe from an acclaimed bakery, top-tier hiking gear, and trail-safety tips from an outdoor pro.

For Extreme Hikers

Those who want to push themselves during their outdoor adventures will find plenty of heart-pounding options in our area. There are several sprawling trails and towering peaks that make for relatively difficult hikes, some of which call for a good deal of experience and trail know-how. Whichever path you select, just be ready for some steep climbs.

Anthony’s Nose
Anthony’s Nose. Adobe Stock / Oldmin.

Anthony’s Nose in Cortlandt Manor is a superlative place to start for a challenging hike. Stretching roughly two miles across the Hudson Highlands State Park Preserve, this demanding trail kicks off with a steep, .6-mile start, followed by plenty of rock scrambles on a path resembling a vertical staircase. The reward is an awe-inspiring view of the Hudson Valley at an elevation of 2,421 feet — and bragging rights, of course.

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Those who want an even more extreme adventure can continue this journey all the way up to Garrison on the Hudson Highlands State Park Preserve’s out-and-back Albany Post to Bear Bridge loop. This 11.3-mile hike normally takes nearly six hours to complete and passes through the 843-foot Canada Hill along the way, just for good measure.

Turkey Mountain Nature Preserve
Turkey Mountain Nature Preserve. Adobe Stock / Peter.

Meanwhile, Yorktown Heights’ Turkey Mountain Nature Preserve boasts a relatively brief hike that packs a real punch. This 831-foot peak sits atop a 125-acre preserve crisscrossed by a 2.1-mile trail loop that leaves many hikers gasping for breath at the end. Once intrepid explorers scale the surprisingly steep ascent to Turkey Mountain’s attractive peak, they can glimpse as far as the New York City skyline, as well as the Hudson Highlands and Croton Reservoir below.

And while it is just beyond the borders of Westchester, any roundup of extreme local hikes must mention Breakneck Ridge. Located in Cold Spring, the ridge’s 3.2-mile Breakneck Loop is considered one of the region’s most challenging and popular hikes, with plenty of rock scrambling over dizzying ledges and steep, slow-going ascents. Just be aware that Breakneck Ridge’s trails recently received a major facelift, so some paths may have shifted from prior jaunts.

For Hikers With Kids

When planning an outdoor adventure with the little ones, an easygoing path with relatively flat topography is a smart choice. We’ve rounded up a handful of hikes with extra-manageable trails — many of them paved — that also sport some fun sights to keep kids entertained along the way.

Westchester RiverWalk
Westchester RiverWalk. Photo by Darlene Ruess.

First up is the Westchester RiverWalk. This incredibly scenic trail might still be a work in progress, but hikers can already enjoy an impressive 32.9 miles of paved and unpaved paths winding through 14 Westchester municipalities. Situated along the Hudson River, the path offers kids virtually nonstop views of the water and cuts through plenty of charming village centers, parks, historic sites, and river-access points, including Peekskill’s Riverfront Green Park and Ossining’s Old Croton Aqueduct, all on an extremely laid-back terrain. Once completed, the RiverWalk will encompass 51.5 miles, with 75% of the proposed route on publicly accessibly lands.

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For a bucolic, tree-lined ramble ideal for family members both in strollers and afoot, the North County Trailway and South County Trailway are both excellent picks. The trail systems are almost entirely paved and trace the path of the now-defunct New York Central Railroad. The South County Trailway winds 14.1 miles, from the border of New York City to Greenburgh, intersecting Yonkers’ Tibbetts Brook Park and Dunwoodie Golf Course. From Greenburgh onward to Briarcliff, Yorktown Heights and Somers, this path becomes the North County Trailway, stretching 22.1 relatively placid miles through sites likes Muscoot Farm and the Kitchawan Preserve, and then continues northward as the Putnam Trailway.

Hammond Museum & Japanese Stroll Garden.
Hammond Museum & Japanese Stroll Garden. Photo by Martin Hara/ Hammond Museum and Japanese Stroll Garden.

Finally, don’t overlook smaller local parks with little ones in tow. Hart’s Brook Park & Reserve, located in Hartsdale, offers roughly 2.5 miles of placid walking paths that cut through a scenic pond, streams, open fields, and rolling lawns of the former Gaisman Estate, where the kids can expend some of that extra energy. Similarly, the Hammond Museum & Japanese Stroll Garden offers 3.5 finely manicured acres of pleasing, easy-to-traverse paths that wind through a bamboo grove, tea garden, and a pond dotted with emerald-hued lily pads.

For Nature Lovers

If gently chirping birds, scuttling squirrels, and a lucky deer or turkey sighting make for your idea of an excellent hike, this is the section for you. While virtually any large natural space in Westchester is a potential opportunity to scope out rare birds and even bigger game, there are a few parks in Westchester that tend to attract animals a bit more than others. Keep in mind, spotting wildlife is never guaranteed, and the time of year significantly impacts what animals are on-site and how many of them you may see.

Edith G. Read Natural Park and Wildlife Sanctuary
Edith G. Read Natural Park and Wildlife Sanctuary. Courtesy of friends of Read Wildflower Sanctuary.

When it comes to jaunts with likely glimpses at fauna, one no-brainer is The Edith G. Read Natural Park and Wildlife Sanctuary. As its name implies, this pastoral paradise on the shores of Long Island Sound in Rye is situated along a migratory flyway, making it home to plenty of birds as well as an abundance of marine life. In fact, the Audubon Society of New York has recognized the Edith G. Read Natural Park as an Important Bird Area.

The 179-acre wildlife sanctuary also holds an 85-acre salt-and-freshwater lake, known for being home to more than 5,000 ducks as well as three miles of trails passing through salt-scented fields and leafy woodland. The sanctuary’s half-mile of publicly accessible shore is additionally a prime spot to catch glimpses of rare aquatic fowl and plants. The nearby Marshlands Conservancy is a similarly superb place to bird-watch in the county.

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Westmoreland Sanctuary
Westmoreland Sanctuary. Photo by Doug Schneider.

Another nature preserve boasting hikes abounding in animals, the Westmoreland Sanctuary in Mount Kisco encompasses an impressive 640 acres of verdant land striped by 8.5 miles of interconnecting trails. The sanctuary’s Nature Center contains plenty of cuddly critters, such as turtles, rabbits, and birds. Guests also have a good chance of spotting plenty of animals outdoors amid Westmoreland’s Terrace Garden, which teems with frogs during warmer months. When it comes to flying friends, Westmoreland is a great place to stop — 139 species of birds have been documented on-site.

Teatown Lake Reservation
Teatown Lake Reservation. Photo by Doug Schneider.

Finally, no roundup of local hikes or nature-focused jaunts would be complete without a nod to Teatown Lake Reservation. A 1,000-acre nature preserve as well as an educational center and nonprofit membership organization, the reservation holds 15 miles of scenic hiking trails, open year-round. The preserve’s gem just might be its two-acre island refuge, which serves as a home to more than 230 species of native wildflower. Visitors can also enjoy onsite wildlife exhibits just in case they want to learn more about all that flora and fauna.

For Day-Hikers

So, you have your water bottles filled, trail mix packed, trekking poles ready, and path all plotted out; in other words, you are ready for one serious hike. If a one- or two-mile ramble just won’t cut it, follow along as we round up day hikes that require at least five hours to complete, each offering a different way to explore a surprisingly broad swath of our scenic county.

Westchester’s largest park is predictably a great place to start when searching for that extra-large hike. With 4,315 sprawling acres of greenery, Ward Pound Ridge Reservation holds an abundance of enjoyable trails, many of which intersect. Originally settled by farmers from Connecticut, the reservation’s main attraction is the 12.2-mile Pound Ridge Loop, which makes for a five-to-six-hour day hike on moderate to challenging terrain dotted with flowering fields, streams, and rocky outcroppings.

The Ward Pound Ridge Reservation is additionally home to the Trailside Nature Museum, in case you want to stretch out your day with some interesting exhibits. Pro tip: Make sure to keep an eye out along the way for the legendary Leatherman’s cave, Native American petroglyphs, and the reservation’s iconic “magic stairs.”

When it comes to top-notch day-length hikes, the Old Croton Aqueduct Trail is a true star. Although this point-to-point adventure stretching from Yonkers to Croton-on-Hudson is an eye-watering 28.5 miles, it only takes roughly eight to 10 hours to complete due to its predominantly flat terrain. The partially paved trail also passes several notable sites, including Croton Dam, and is known as a top spot for biking and horseback riding in addition to walking and hiking.

Rockefeller State Park Preserve
Rockefeller State Park Preserve. Adobe Stock / Linda Harms.

Finally, while this park doesn’t have a single trail as lengthy as the two mentioned above, the Rockefeller State Park Preserve is perhaps one of the finest spots in the county for a day on the trails. With an incredible 45 miles of interconnecting paths formed from the estate’s crushed-stone carriage roads, hikers can customize their ramble to fit their fancy, ranging from a four- or five-hour jaunt to a 12-hour (or more) journey through some of the county’s most scenic environs.

For Water Views

What walk in the woods is complete without a view of the water? Here are three local retreats offering easy to brisk hikes that reward visitors with year-round, shoreline vistas.

Oscawana Island Nature Preserve has hikes in Westchester
Oscawana Island Nature Preserve. Photo courtesy of Town of Cortlandt.

Winding along the Hudson River shoreline in the town of Cortlandt’s hamlet of Crugers, Oscawana Island Nature Preserve is a compact slice of ideally situated Westchester County parkland. Visitors to the 161-acre preserve’s several miles of dirt and gravel trails are treated to unobstructed views of tidal marshlands teeming with birds and aquatic life that is especially alluring during the morning hours.

The preserve is bisected by Metro-North Railroad’s Hudson Line, and a bridge above the rail tunnel leads hikers to stunning river vistas in all directions. The path also passes ruins of an estate that dates to the Victorian era. The preserve, whose name is of Native American origin, is not to be confused with Oscawana Lake in Putnam Valley.

The pristine Silver Lake Preserve and the 236-acre park that encompasses it are only two miles from the heart of Downtown White Plains. And although you can glimpse the city’s skyline from its highest points, you won’t hear any of its urban clatter. The preserve’s 4.8-mile trio of connecting trails feature steep ravines terraced with wide, stone steps, with the white-blazed trail tracing the west shore of the lake.

Known during Colonial times as Horton’s Pond, the preserve is steeped in history. The Heritage Trail passing Revolutionary War landmarks — marked with red-white-and-blue blazes — can be accessed from the preserve’s paths, and a historical marker at the trailhead commemorates the battle of Merritt Hill. The acreage was home to The Hills, an African American community, and is adjacent to Stony Hill Cemetery.

Spitzenberg Mountain has hikes in Westchester
Spitzenberg Mountain. Photo by Frank Roberts.

Spitzenberg Mountain’s moderately challenging 1.6-mile out-and-back is part of the Westchester County parks system’s sprawling 1,538-acre Blue Mountain Reservation in Peekskill. The trailhead is tucked behind Blue Mountain’s Sportsman Center, next to an archery range. Hikers arriving at the 550-foot-high summit’s rocky outcropping, with expansive views of the Hudson River and environs, also discover the ruins of a fire observatory.

This trail carved into the park’s steep southern corner is shared with mountain bike riders who are generally courteous. It’s located a safe distance from the reservation’s shooting range, although still within earshot. The Spitzenberg trailhead can be entered from Blue Mountain’s trail system via the Briarcliff-Peekskill Trailway. —Robert Brum

The Future of Your Way

If you find yourself on a trail wondering which way to go or where you can get help should something go awry, there is now an answer on several Westchester hikes. Founded in 2018, Smart Outdoor Inc. has been working with the county to outfit several area trails with their innovative tech.

Smart Outdoor Inc. helps with hikes in Westchester.
Smart Outdoor Inc. has been working with the county to outfit local trails with QR codes than can help hikers find their way or contact help. Courtesy of Smartoutdoor Inc.

Based in Westchester and Putnam counties, Smart Outdoor Inc. outfits pathways with smart-trail signage as well as mile markers equipped with QR codes. These codes allow hikers to access a wealth of useful information, including trail rules and maps, restroom locations, local weather, area businesses, and events. Additionally, all GPS located signs and markers connect to the county’s 911 system, allowing first responders to quickly locate users in need of assistance.

Courtesy of Smartoutdoor Inc.
Courtesy of Smartoutdoor Inc.

So far, Smart Outdoor has outfitted county sites like the Bronx River Pathway as well as the North County Trailway and South County Trailway. According to Smart Outdoor Inc.’s founder and president, Ivan Bellotto, the signage marks a major jump in trail-safety tech. “By placing QR codes strategically along trails, Smart Outdoor enables users to access a wealth of information about the trail, local businesses, and emergency services,” says Bellotto. “What sets Smart Outdoor apart is their commitment to local municipalities, providing signage implementation at little to no cost through primary sponsorships.”

Bellotto adds that “all signs and mile markers are uploaded to the CAD 911 systems, facilitating direct 911 dispatch in case of emergencies.” he says. “This comprehensive approach ensures that trails become more informative, engaging, and safer for communities to enjoy. Perhaps best of all, Smart Outdoor’s national debut of this technology was in Westchester.

Top Trail-Safety Tips

When it comes to outdoor activities, safety should always be first. In that spirit, we asked Rye Nature Center’s associate director of forest, preschool, and camp, Emily Embick, for four hiking-safety tips that could save a life.

hikes in Westchester
Blackday / Adobe Stock

Plan Your Hike

“The most important thing is to know where you are going and to plan your hike. If you’ve never done [a particular hike] before, it’s important to know what trail markers you are looking for, how long the hike should take, and what challenges there are along the trail. AllTrails is a great app to use if you want to have a map on your phone. … Some places also have PDFs of maps on their websites. Also, make sure to double-check the park’s website to make sure there aren’t any alerts about the trail, such as trail work.”

Pack Smart

“Next, plan out your gear and what you are going to bring with you. Many people don’t want to carry a daypack, but it is better to have extra stuff and not need it than to need stuff that you don’t have. So, for the kids we are always carrying extra water, a first aid kit, sunscreen, bug spray, and snacks. Even if it’s just a day hike, you might find yourself off-trail and be hungry. Bug spray is also very important. So, you want to be a little over prepared, I’d say.

Dress for the Occasion

“What you are wearing is important. I prefer hiking boots that have a little ankle support. It really helps when you are on more rugged terrain or a rocky hike, so you don’t roll your ankle. As for socks, I wear wool socks — the shorter, boot-cut wool socks, even in the summer. I know some people will even wear the higher socks so that they can put them over their pants to protect from ticks. I know in the summer, when it’s hot you don’t want to wear pants, but if you can find some lightweight, breathable hiking pants those are always going to be better than shorts to protect from ticks and bugs.”

Tell Someone

“If you are doing a hike where you know you won’t have good service, a strenuous hike, or are going to be alone, make sure someone knows where you are going that day. It’s a good plan to call a family member or a friend and say, ‘Hey, I am hiking here today, and this is what time I plan to return.’ It is always good to have that extra layer of protection.”

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