Fall Hiking Guide for Westchester and Beyond 

Writer and photographer Larry Epstein atop Anthony’s Nose.

If the bugs bug you, and the heat drains you, fall is the perfect time to hike. Westchester has a variety of trails and parks that are perfect for people of all ages and abilities who want to enjoy the great outdoors.  

And nearby in Putnam and Dutchess counties, the hills get higher, and the views get better. 

But let’s start close to home – here in Westchester. 

Ward Pound Ridge Reservation 

Ward Pound Ridge Reservation, and its 4,315 acres, is the largest park in the county.  

According to AllTrails, the park contains 13 trails ranging in length from 2 miles to 12 miles. 

The shorter and flatter ones are perfect for the entire family, but the Leatherman’s Loop is the longest and most challenging one – and hiking it is an all-day affair. 

If you’d rather enjoy the park, without walking too far, it also contains areas for picnicking and fishing. 

Croton Gorge Park 

Croton Gorge trail.

The trails are beautiful – and the gorge is gorgeous. 

This 97-acre park at the base of the Croton Dam has lovely views of the dam itself, and the spillway. 

The Croton River also starts in the park, so there is a lot to explore here. 

You can walk on the road atop the dam or check out the 1.5-mile loop. 

That’s a relatively flat walk that’ll give you a nice view of the river. 

The park is also a popular spot for picknickers and families, as kids can enjoy the playground. 

Teatown Lake Reservation, Ossining 

Teatown is a 1,000-acre nature preserve featuring 15 miles of hiking trails, and a 41-acre lake. 

More than 10,000 hikers use the trails each year, and it’s also a popular spot for jogging and cross-country skiing. 

The trails range from easy/novice to moderately difficult – and the area is known for its incredible diversity of native flowers, trees – and varied terrain.  

And if you want to keep going – The trails connect to the Briarcliff Peekskill Trailway and the Croton Aqueduct Trail. 

Anthony’s Nose, Cortlandt Manor 

View of the Bear Mountain Bridge from Anthony’s Nose.

Anthony’s Nose is the cliff you see looming over the east side of the Bear Mountain Bridge. 

You can park on Route 9D and take a well-marked trail to the top in about 30 minutes at a good pace.  

It’s about a mile long, and most of the trail is comprised of steep rocky steps.  

From the top you get a bird’s eye view of the bridge, a stunning vista down the Hudson, and a magnificent look at Bear Mountain across the river. 

Hiking the Highlands 

Breakneck Ridge in Cold Spring is the most popular hiking spot in the area, but it’s mostly closed while undergoing a renovation and transformation that will last two years. 

Don’t worry though – there are tons of other options available to get out there and hike. 

Hudson Highlands State Park Preserve is right in our backyard.  

It’s a rugged wilderness that stretches from Peekskill to Beacon, containing 70 miles of trails winding through 8,000 acres of hills, mountains and forests.  

Roughly half a million people each year visit the preserve to hike and sightsee. 

Mount Beacon 

View from Mount Beacon.

About 15 miles north of Anthony’s Nose you’ll find Mount Beacon – the tallest peak in the Highlands topping out at more than 1,600 feet. 

On a clear day, from the top, you can see the Manhattan skyline more than 60 miles away.  

The most popular starting point is the parking lot on Route 9D.  

From there it’s about a three-quarters of a mile climb, up steep setbacks, to the first plateau. 

It’s about 900 feet above sea level, and from up there you get a panoramic view of the Hudson Valley and the Newburgh-Beacon Bridge.  

But you can make it there in about 30-40 minutes, and it sure is worth the hike.  

And if you still have some gas in the tank, you can keep following the trail for another mile and a quarter or so, and you’ll arrive at the fire tower that affords incredible views from New York City to Albany on a clear day. 

So, pack up your sunscreen, water, and some snacks – and head out for a hike. 

Around here, we’re lucky enough to have an incredible diversity of options. 

All photos by Larry Epstein.

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About the Author: Larry Epstein