Westchester hiking doesn’t get enough credit. We’re sandwiched between the city and the Hudson Valley, and people assume you have to drive two hours north to find a decent trail. You don’t. There are hundreds of miles of trails right here, from flat paved paths to legit scrambles that will have your legs burning the next day.
We’ve hiked most of them. Some are fantastic. Some are fine. A few are honestly overrated. Here’s what we actually recommend.
The ones everyone knows (for good reason)
Rockefeller State Park Preserve, Pleasantville/Sleepy Hollow
If you only hike one place in Westchester, make it Rockefeller. The Rockefeller family donated this land, and the trail system is built on old carriage roads that are wide, well-maintained, and gorgeous year-round. There are over 30 miles of trails here, so you can do a quick 2-mile loop or spend half the day.
The trails around Swan Lake are the most popular, and they’re popular for a reason. In fall, the foliage reflecting off the water is absurd. Go on a Tuesday morning if you can. Weekends in October are a zoo.
The details: Free parking at the main lot off Route 117. Dogs allowed on leash. Easy to moderate depending on which trails you pick. The carriage roads are wide and mostly flat, but some of the single-track trails that branch off have real elevation.
Old Croton Aqueduct Trail, multiple towns
This one runs 26 miles from the Croton Dam all the way down to the Bronx, following the route of the original aqueduct that brought water to New York City in the 1840s. You don’t have to do the whole thing. Most people pick a section and do an out-and-back or arrange a car shuttle.
The stretch through Sleepy Hollow and Tarrytown is our favorite. You pass right by the Old Dutch Church and Sleepy Hollow Cemetery, and there are spots where you can see the Hudson River through the trees. The trail is mostly flat and packed dirt, so it’s good for a casual walk or a long run.
The details: Multiple parking areas along the route. Free. Dogs welcome. The whole trail is pretty easy, with minimal elevation change. It’s also one of the few trails in Westchester that’s reasonable for strollers in dry weather.
Untermyer Gardens and Park, Yonkers
Untermyer is more of a destination than a hike, but we’re including it because it’s one of the most striking places in the county and a lot of people still haven’t been. The Walled Garden is wild. Persian-inspired architecture, mosaics, columns, panoramic views of the Hudson and the Palisades. It feels like it shouldn’t exist in Yonkers.
There are trails in the surrounding park if you want to walk more, but honestly, most people come for the gardens and the views. It’s worth a visit even if you’re not a hiker.
The details: Free. Small parking lot that fills up on nice weekends, so arrive early or park on the street. The gardens are open daily, dawn to dusk. Not really dog-friendly in the formal garden areas.
Easy walks for when you’re not feeling ambitious
Cranberry Lake Preserve, White Plains/North White Plains
This is one of the best spots in Westchester for an easy, no-pressure walk in the woods. The trails loop around a pretty lake and through hardwood forest. The whole preserve is about 190 acres, and the main loop is around 2.5 miles. It’s flat, well-marked, and shaded, which makes it great in summer.
There’s a small nature center near the entrance that’s worth poking into if it’s open. Cranberry Lake doesn’t get the Instagram attention that Rockefeller does, and that’s part of why we like it.
The details: Free parking. Dogs are not allowed here, which is a bummer for dog owners but means the trails stay quiet. Easy difficulty.
Teatown Lake Reservation, Ossining
Teatown is a 1,000-acre nature preserve with about 15 miles of trails, and it’s one of the most well-run spots in the county. The trails range from flat lakeside paths to steeper woodland loops. The Lakeside Trail is a mellow 2-mile walk around the lake that’s good for families.
If you want something a little harder, the Hidden Valley Trail adds some hills and takes you through meadows and deeper forest. Teatown also runs a lot of educational programs, so check their calendar if you’re into that.
The details: Non-member parking is $5 on weekends, free on weekdays. Dogs are not allowed. Easy to moderate.
Real hikes that’ll tire you out
Ward Pound Ridge Reservation, Cross River
This is the biggest park in Westchester at over 4,300 acres, and it’s the closest thing the county has to backcountry. If you want to get away from people, this is where you go. There are 35+ miles of trails, and some of the routes in the interior feel genuinely remote.
The trail markings can be a little inconsistent, so download a map (or bring AllTrails) rather than winging it. The Leatherman Loop is a solid 5-mile route with some good climbing. In spring, the wildflowers along the trails are really something.
One thing to know: there’s a parking fee for non-residents ($10 on weekends in season, $5 on weekdays), and it’s strictly enforced. Worth it.
The details: Dogs allowed on leash. Moderate to strenuous depending on your route. Bring water. There are lean-to shelters for picnics scattered around the park.
Blue Mountain Reservation, Peekskill
Blue Mountain is underrated. It’s a solid hike with real elevation gain (the summit is about 680 feet), and the trails are rocky enough to feel like you’re actually working. The main loop to the top and back is about 4 miles.
The views from the top aren’t panoramic, but you get nice glimpses of the river through the trees. On a clear day, you can see the Bear Mountain Bridge. The trails connect to other parks in the area, so you can extend your route if you want.
The details: Free parking. Dogs allowed on leash. Moderate to strenuous. The rocky sections can be slippery when wet, so save it for a dry day.
Anthony’s Nose, Cortlandt/Bear Mountain area
Okay, this one is technically right at the border of Westchester, but it’s close enough and good enough that we’re counting it. Anthony’s Nose is a steep, direct climb that rewards you with one of the best views in the entire Hudson Valley. You look straight down at the Bear Mountain Bridge and across to Bear Mountain itself.
The hike is about 3.5 miles round trip from the Camp Smith Trail parking area, with roughly 900 feet of elevation gain. It’s steep in places and can be rocky, but it’s short enough that most reasonably fit people can handle it. Bring a snack for the top.
The details: Free parking at the trailhead on Route 9D (technically Putnam County side) or at the Camp Smith Trail lot. Dogs allowed. Strenuous but short. Go early on weekends, especially in fall. The parking lot fills up fast.
Waterfall and river trails
Mianus River Gorge, Bedford
This is one of our absolute favorites and one of the most underrated spots in the county. The Mianus River Gorge was the first property protected by The Nature Conservancy, back in 1953, and walking through it you can tell this forest has been left alone for a long time.
The main trail is about 5 miles and follows the river through a hemlock gorge. There’s a cascade that’s especially pretty after rain. The forest here feels old, with massive trees and a quiet that’s hard to find this close to New York City.
The details: Free, though donations are encouraged. Open April through November. Dogs are not allowed. The trails close at 5 PM. Moderate difficulty with some uneven terrain. The preserve has a small parking area that can fill up, so weekday visits are easier.
Croton Gorge Park, Cortlandt
The park sits at the base of the New Croton Dam, and the waterfall spillway is the main attraction, especially after heavy rain when the dam is releasing water. It’s dramatic. The park itself has picnic areas and connects to the Old Croton Aqueduct Trail, so you can combine them.
It’s more of a short walk than a hike, but the dam views are worth the trip.
The details: Parking is $10 for non-residents in season. Dogs allowed. Easy.
Best for fall foliage
Almost every trail in Westchester is better in fall, but a few stand out.
Rockefeller’s Swan Lake trails are probably the single best spot for fall color, especially in mid to late October. The reflection of the trees in the water is cliche-level beautiful, but it earns it.
Ward Pound Ridge has the variety. Because the park is so big and has different elevations and forest types, you’ll see maples, oaks, and beeches all changing at slightly different rates. It’s less manicured than Rockefeller and more wild.
The Old Croton Aqueduct through Sleepy Hollow has the atmosphere. Walking through the cemetery and past the church with the leaves turning is peak Westchester fall. It’s exactly what you’re picturing.
For something smaller and quieter, try the trails at Muscoot Farm in Somers. It’s a county-owned farm with gentle walking paths through fields and along the Muscoot River. The combination of farm views and fall colors is really nice, and it rarely feels crowded. Plus, the animals are there. It’s not a hike, it’s a walk. But it’s a good one.
A few honest opinions
Most overrated: Saxon Woods Park in White Plains. It’s fine for a quick walk, but the trails are short and the park leans more toward the pool and playground crowd. Not bad, just not a destination for hiking.
Most underrated: Mianus River Gorge, easily. People drive right past Bedford on their way to harder hikes up north and miss one of the most beautiful forests in the region.
Best bang for your buck: Rockefeller. Free parking, tons of trails, beautiful in every season. It’s popular for a reason.
Best for dogs: Ward Pound Ridge and Blue Mountain both let your dog off-leash in designated areas during certain months (check the county parks website, as the rules change). If your dog needs to run, those are the spots.
Best early morning hike: Anthony’s Nose. Get there at 7 AM on a Saturday, beat the crowds, and have the summit to yourself with your coffee.
Tips from people who’ve been
- Go on weekdays if you can. The popular trails (Rockefeller, Untermyer) are noticeably more pleasant without the weekend crowds.
- Most Westchester County parks charge non-resident parking fees ($5-$10). A county parks pass pays for itself fast if you go regularly.
- Bring bug spray from May through September. The ticks in Westchester are no joke. Do a tick check after every hike, especially if you’ve been in tall grass.
- AllTrails is useful for Westchester trails, but the crowd-sourced difficulty ratings tend to skew easy. If someone on AllTrails says a trail is “moderate,” assume it has some real hills.
- Spring is mud season. The trails at Ward Pound Ridge and Mianus River Gorge can get soggy through April. Pack boots or wait for a dry stretch.
Come hike with us
Club West runs group hikes throughout the year. It’s a low-key way to explore new trails with other women in the area, and we always pick good ones. Check our upcoming events or sign up to get on the list.
Trail conditions change with weather and seasons. Check with the individual park or preserve before heading out, especially after heavy rain or during winter months when trails may be icy or closed.