11 Amazing Hiking Trails in Westchester County

Mar 23, 2023

Dust off your hiking boots and get ready to explore. 

If soaking in the great outdoors is high on your suburban lifestyle list, we’ve got some amazing options for you. These Westchester hiking trails are ideal destinations for spring. Not only will you get a good workout in, but you’ll get breathtaking views of the county and beyond — and a good sense for what life could be like in suburbia. 

#1. Bronx River Parkway Reservation, Bronxville

Bronxville is home to Westchester’s oldest park with a paved path stretching over 11 miles. Locals love visiting this park for cycling, running and hiking. Dogs are also welcome to use the path as long as they stay on leash.

Check out Bronxville’s food scene after exploring the park. This town has some hotspots including Ernie’s Wine Bar + EATS, Scalini Osteria and La Casa Bronxville.

#2. Teatown Lake Reservation, ​​Ossining

This Ossining gem is home to 15 miles of scenic lakeside trails ideal for walking, hiking, and biking. In addition to the trails, this preserve offers tours of a unique floating garden known as Wildflower Island, along with family-friendly programs like guided nature walks, art exhibits and volunteer opportunities.

Looking for a bite to eat after the hike? Book a table at 3 Westerly Bar and Grill for a meal with a view or stop by Sing Sing Kill Brewery if you’re in more of the mood for a post-hike beer.

#3. Croton Gorge Park and Croton Point Park, Croton-on-Hudson

Croton-on-Hudson is a nature lover’s dream. Between the waterfall trails at Croton Gorge Park and kayaking opportunities at Croton Point Park there’s always something to do outside, whether it’s sunny, snowy, or something in between. 

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If the weather is on the warmer side, be sure and pack a picnic – and then stop by The Blue Pig for dessert. Nothing says summer in the suburbs more than a scoop of their homemade ice cream.

#4. Tarrytown Lakes Park, Tarrytown

Bring your four-legged friend along when you head to Tarrytown. Tarrytown Lakes Park includes 4 miles of dog-friendly trails, plus spots for biking, canoeing and kayaking.

Tarrytown is easily accessible to Manhattan and other Hudson River towns via the Metro-North line. Main Street sits a few blocks from the train station and features some excellent eateries like Sweet Grass Grill which serves up seasonal farm-fresh fare.

#5. Rye Nature Center, Rye

The 47-acre Rye Nature Center offers summer camps for kids and other community programs (hello, composting). There are multiple trails for hikers of all levels, each with great views of the turtle ponds and wildflower fields.

When you’re done, make your way from the nature center to the micro-chain Village Social – there’s another outpost in Mt. Kisco. From craft cocktails to brussels sprouts pizza, this popular spot has something for everyone.

#6. Hillside Woods and Park, Hasting-on-Hudson

Hillside Woods and Park is home to scenic trails, ballfields and a playground. This 100-acre woodland is a peaceful place to clear your head or take your dog for a walk. There’s even a small fishing pond that’s a favorite with young families. 

Pair your hike with a visit to Boro6 in the heart of town. It’s a Michelin Bib Gourmand spot with tapas and an A+ wine selection.

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#7. Rockefeller State Park Preserve, Mount Pleasant

Picture 45 miles of repurposed carriage roads that are beautiful no matter the weather and you’ve got Rockefeller State Park. Summer is the best time for hiking but the fall foliage is hard to beat and winter is incredible in its own right.

Stop into Wood & Fire for Neapolitan Style pizza or The Barley House to relax on a patio under twinkling string lights.

#8. Whippoorwill Park Loop, Chappaqua

The rugged 3.5-mile Whippoorwill Park Loop takes hikers through woodlands and past streams and ponds. It’s a calm park with benches along the trail if you want to sit and enjoy the scenery. Plenty of locals bring their dogs along for the trek.

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Whether you’re craving tacos or want a French bistro experience, there are tons of options in the heart of Chappaqua for a post-hike meal. 

#9. Mianus River Gorge Preservation, Bedford

For an easy stroll, consider the 5-mile trail in Mianus River Gorge. It’s great for families with kids or anyone who wants an accessible hike that still offers waterfall views.

Locals also love spending summer days at Bedford Village Memorial Park. While some days call for a poolside picnic, Truck and Ristorante Lucia are two great options if you’re looking for a sit-down meal. 

#10. Eugene and Agnes Meyer Preserve, Armonk

Trail runners love the roads less traveled at Eugene and Agnes Meyer Preserve. These trails don’t get as crowded as some of the others on the list so you won’t have to worry about weaving in and out of hikers. But if you do want to hike, don’t worry, there’s plenty of room for everyone to soak in the forest and wildflower views.

Main Street is filled with top-notch restaurants so take a stroll to decide if you’re in the mood for pizza, steak or sushi.

#11. Silver Lake Preserve, White Plains

With over 200 acres and 5 miles of trails to explore, each visit to Silver Lake Preserve offers a new experience. Take in the fresh air and keep an eye out for historical markers so you can learn more about the area’s colonial-era history.

Book a reservation at Freebird Kitchen and Bar for a Southern-style brunch or Serafina if you want a taste of Manhattan in the ‘burbs.

Want to start exploring the suburbs this spring? Let’s chat! Contact us today to schedule your FREE suburbs strategy session.

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