From Climbing To Biking, Birding To Hiking, The Westchester Area Has A Trail For Every Trekker

Bang for Your Buck: Storm King State Park

(1 Mountain Rd, New Windsor, NY)

When it comes to getting the most out of your hike, Christopher and Catherine Brooks, authors of 60 Hikes Within 60 Miles: New York City, don’t have to think too hard about the perfect trail. They recommend Storm King for the payoff it provides in sweeping views of the Hudson after a moderately strenuous hike that’s just less than four miles. All this, and it’s easily accessible off Route 9 West. The trail ascends more than 1,200 feet along the way, but, according to the Brookses, the views you’ll encounter are so striking that it’s easy to get distracted and forget all the climbing you’re actually doing. “The climb requires a bit of stamina,” says Christopher, “but every viewpoint yields a ready excuse to catch your breath.” Or, take it away.

For Trailrunners: Colonial Greenway

(Parking/points of access include: Saxon Woods Park, 1800 Mamaroneck Ave, White Plains; Maple Moor Golf Course, 1128 North St, White Plains; River Ridge Equestrian Center, 960 California Rd, Eastchester.)

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April may be the cruelest month, but, for runners, it’s usually a fine time to get back outdoors if the cooler temps have kept you on treadmills all winter. Jane Daniels, author of Walkable Westchester, out later this month in its second edition, recommends the Colonial Greenway for those seeking some of the best trail running in the region. Totaling 15 miles, these trails meander through nature preserves, woods, and wetlands. Daniels notes that because it links seven parks along the way, “there are always options to expand or contract one’s run, and the rolling terrain is easy on the feet.” Start running the trails in the spring, and you can gear up for fall’s Paine to Pain Half Marathon—which relies on the Colonial Greenway for the majority of its course, but never uses the same section of trail more than once.

For Leaving It All Behind: Teatown-Kitchawan Trail

(Take the Taconic State Parkway to Rte 134 W towards Ossining. Make a right onto Spring Valley Rd, turn onto Blinn Rd, and follow to lakeside parking lot.)

Sometimes getting lost in the woods isn’t a bad thing. For a hike that lets you feel like you’ve run away, but not too far away, the Teatown-Kitchawan Trail, known as the TK Trail, is just the thing. Notes Daniels, “It’s hard to believe where you can go from this trail. From Teatown Lake Reservation, the trail heads east to connect to John E. Hand Park and Kitchawan Preserve. It is a direct link to the Briarcliff-Peekskill Trailway and indirectly to the Old Croton Aqueduct and North County Trailway.” The scenery is incredibly varied; the trail travels through wetlands, hills, valleys, and meadows. Futhermore, Daniels explains, “by passing through an isolated portion of pristine New York City Department of Environmental Protection property, it provides a peaceful setting for hikers.” Who needs yoga when you can get your zen fix in the great outdoors?

Most Accessible: RiverWalk Park at Tarrytown

(250 W Main St, Tarrytown)

Think you have to hike deep into the woods or up a mountain to get views of the natural world worth Instagramming? Think again. Tarrytown’s section of Westchester’s RiverWalk is as swoon-worthy as it is reachable. Close to public transportation (the train station is within walking distance), this ramble along the river offers views of everything from the Tappan Zee Bridge to the Manhattan skyline. It’s one part of a larger plan Westchester County has to create a 51-mile trail that will ultimately stretch from Yonkers all the way to Peekskill. Short and sweet at a little over a half-mile, this gem of a jaunt won’t have you needing to sit and rest, but you just might want to stop at one of the trailside benches and smell the (beach) roses sprinkled along the way.

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For Birders: Croton Point Park

(1A Croton Point Ave, Croton-on-Hudson)

More than 500 acres of land and a good chance of spotting eagles and hawks? If you aren’t sold yet, allow us to elaborate. This park, located on a peninsula on the Hudson River’s east shore, offers as many forms of fun as types of birds. Well, to be honest, there are probably more of the latter; it’s possible to spot sparrows, mockingbirds, bald eagles, red-tailed hawks, and even the occasional short-eared owl here. The park’s Nature Center offers a variety of programs that will give you the chance to learn about your natural surroundings. In the warmer weather, camping, grilling, boating, fishing, and swimming are available to supplement your walk.

Summer Hike: Harriman State Park—Pine Meadow Lake

(Reeves Meadow Visitor Center, Seven Lakes Dr, Ramapo, NY)

No discussion of hiking around the tri-state area would be complete without Harriman State Park. Encompassing over 46,000 acres, it is the second largest state park in New York, and includes 200 miles of hiking trails. With its craggy peaks and rocky domes, “it almost resembles the Sierra Nevadas,” says Christopher Brooks. But with so much mileage available, where to start? Try the five-mile round-trip hike to Pine Meadow Lake, which takes the cake for a scenic trek on hot days. While the crowds get pretty thick on trails throughout the park, especially on weekends, it’s for good reason, and worth braving. After a moderate, partially shaded hike along a stream, you will be rewarded with views of the lake, and a chance to dip your tired toes in its cool waters. Although swimming is technically prohibited here, Eileen West, vice president and hike coordinator of the Westchester Trails Association, says the shores of the lake provide their own form of fun, “with plenty of places to relax on rock outcrops overlooking the lake.” Pack a picnic lunch and call it a day, or at least an afternoon.

For Wildlife: Bennett’s Pond State Park

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(From I-84 East or West, take Exit 3 to Rte 7 South; then after 3.6 miles, make a right onto Bennett’s Farm Rd, Ridgefield, CT)

This tract of land, 460 acres now known as Bennett’s Pond State Park, was rescued from development back in the late ’90s, and thankfully so. It offers an eight-mile hike (with the option to shorten) through towering maples and pines, past tranquil ponds (one of which is its namesake), and meandering old stonewalls. Moderate in difficulty, the hike consists of two connected loops with undulating trails of packed dirt and rocks. Along the way, in addition to the multitude of birds you are likely to spot, there are wild turkeys, coyotes, foxes, deer, and beavers that call this acreage home. Swans slowly making their way across Bennett’s Pond are the very picture of tranquility, and the Brookses point out that “amateur naturalists will discover an abundance of wildflowers as well as mushrooms in the fertile ground.” At the crest of the hike, the remains of a cabin rumored to have belonged to the composer Charles Ives still stand, the lone reminder of the world outside this oasis.

For Adrenaline Junkies: Indian Head Mountain Loop

(Take the NYS Thruway to Exit 20; then make a left onto NY 212/NY 32. Stay straight for about two miles; make a right onto County Route 35. Make a left after 1.5 miles to stay on Rte 35-West Saugerties Rd. Continue until it becomes County Rte 33 and then Platte Cove Rd. Just before this road crests, turn right at the “Trailhead Parking” sign.)

When you think of the Catskills, you most likely think of steep, rocky climbs with some intimidating elevation—and you wouldn’t be mistaken. The Catskill Park encompasses some 600,000 acres of land, and when it comes to a serious workout, this hike up Indian Head Mountain stands out as a favorite. Reaching over 3,500 feet in elevation, there’s a reason it’s part of the Devil’s Path, a trail through the Catskills known for being the most treacherous and difficult (think sheer wallfaces to scale, chimney climbs, and danger of falling off ledges). Getting to the summit on this 7.8-mile hike necessitates using both hands and feet at times, and it’s not a trek for the faint of heart.

When approached with a healthy dose of caution (we don’t recommend bringing children or dogs) and preparation (pick up a trail guide ahead of time and estimate being out on the trail at least six hours), however, Indian Head offers up magnificent views and a truly heart-pounding hike. Daniel Chazin, author of Hike of the Week: A Year of Hikes in the New York Metro Area and Board member of the Publications Committee for the New York-New Jersey Trail Conference (—a wonderful resource for information on hikes in the area—has been climbing the Catskills for over 30 years, and he explains that people flock here for its “rugged wilderness.” Besides the awe-inspiring views, he says, “It’s more remote, more challenging, and there’s more elevation.” And we’re guessing, more fun.

Day Trip: Overlook Mountain

(Trailhead is directly across from 335 Meads Mountain Rd, Woodstock, NY)

If you’re in the mood to explore the Catskills without the challenge of the Devil’s Path, Lisa Berger, deputy director for Ulster County Tourism, recommends a hike up Overlook Mountain for stunning scenery without the anxiety of 100-foot drops (but watch out for timber rattlesnakes). After a pretty steady climb of about two miles (the hike is five to 10 miles round-trip, depending on your route), you’ll come to the rather eerie remains of the Overlook Mountain House, one of many hotels erected to cater to travelers visiting the Catskills throughout the 19th and 20th centuries. For some amazing scenery, continue on to the old fire tower, where a quick climb yields incredible views of the surrounding peaks and the Ashokan Reservoir. Once you’ve found your way back down, head into the eclectic town of Woodstock for some antique shopping, gallery hopping, and a well-deserved bite to eat.

Historical Hike: Morristown National Historical Park—Jockey Hollow Run

(From I-287 New Jersey North or South, take Exit 30B and turn right at the traffic light onto Rte 202 North. Then turn left at the light for Tempe Wick Rd-Rte 646 and continue for another 1.5 miles until reaching the entrance to the trail.)

We know, we know—for the average Westchesterite the words “New Jersey” aren’t exactly synonymous with historic or idyllic, but you might have to adjust your thinking because that’s just what you get on this easy five-mile hike through Morristown National Historical Park. During the Revolution, George Washington rested his troops here during the harsh winter of 1779 to 1780, and re-creations of the soldiers’ huts remain on view as a testament to that brutal time. While traversing gentle grassy hills and thick forests, you’ll also encounter the Wick House, which served as officers’ quarters at various times throughout the Revolution. Legend has it that in 1781, Mr. Wick’s daughter, Temperance, hid her horse in her bedroom rather than have it seized for use by soldiers. 

More outdoors: The Top Outdoors Activities in Westchester

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