The Best Trail Running Routes in the Hudson Valley (Starting in Chester, NY)
The Hudson Valley doesn't get enough credit as a trail running destination. Most people default to the Catskills or the Appalachian Trail corridor, but right here, within 45 minutes of Chester, NY, there's some of the best trail running in the Northeast. Ridgeline scrambles, technical singletrack, sustained climbs with river views, and enough vertical to humble any runner. These are four trails worth knowing, what to expect on each one, and where to refuel once you've actually earned it.
What makes Schunemunk Mountain the best trail run near Chester, NY?
Schunemunk Mountain is the closest serious trail run to Chester, with the trailhead less than 10 minutes from town, and it earns its place as the essential local loop. The Jessup Trail makes a roughly 7.5-mile circuit with about 1,600 feet of elevation gain, taking you through dense oak forest before breaking out onto a dramatic ridgeline of dark conglomerate rock called puddingstone, a geological formation found in almost no other place on Earth.
The views from the summit stretch west toward the Catskills and east across the Hudson Valley. On a clear morning after a hard climb, it's the kind of moment that reminds you exactly why you run trails instead of roads. The middle section of the ascent is where you find out what you've got: sustained, relentless, no technical shortcuts. If you live near Chester and haven't run Schunemunk yet, fix that this weekend.
Distance: 7.5 miles | Elevation Gain: ~1,600 ft | Difficulty: Moderate to Hard
After the run: Drive 20 minutes west to Bellvale Farms Creamery in Warwick. It's a working dairy farm with homemade ice cream and views of rolling farmland and hills that pair well with post-run legs. You'll wait in line on weekends. Get two scoops anyway.
Is Harriman State Park worth the drive for trail runners near Chester?
Harriman State Park is worth every mile of the 25-minute drive south from Chester, and it's not a close debate. With over 200 miles of marked trails across 47,000 acres, Harriman is one of the most trail-dense parks on the entire East Coast. Whether you want a 6-mile recovery run or a 20-mile sufferfest, the system delivers.
The Pine Meadow Lake loop is the go-to for most runners hitting Harriman for the first time: roughly 8 miles, moderate elevation, well-marked trails, and a lake at the finish that's perfect for cooling off in summer. If you want to push further, the Ramapo-Dunderberg Trail runs nearly 24 miles end to end with exposed ridgeline sections, relentless climbing, and technical descents that will test everything you've built in training. Harriman also rewards return visits, because the trail network is big enough that you can run there a hundred times and still find new routes.
Distance: 6-24 miles | Elevation Gain: 800-3,500+ ft | Difficulty: Moderate to Very Hard
After the run: Head into Tuxedo or Sloatsburg for food. Small towns, honest spots, the kind of no-frills dining that fits a post-trail mindset better than anywhere requiring a reservation.
What can you find running the trails at Black Rock Forest near Cornwall?
Black Rock Forest is 4,000 acres of mixed terrain about 20 miles from Chester, with roughly 20 miles of trails split between wide carriage roads and tight, rooted singletrack, and one of the lowest crowd levels of any trail system in the region. Because it's an active science preserve, there are no mountain bikes and no horses. On a weekday morning, you can run the entire loop without seeing another person.
The summit of Black Rock Mountain sits at 1,410 feet with open views toward the Hudson River and Storm King to the south. A well-traveled loop hits the summit and circles back through the reservoir area, covering about 6 miles with 1,100 feet of gain. The trails also link into the Appalachian Trail corridor if you want to tack on more distance.
What sets Black Rock apart isn't the raw difficulty. It's the silence. No interruptions, no weekend crowds, just you and the trail. That's increasingly rare in the Hudson Valley and worth every minute of the drive.
Distance: 6-10 miles | Elevation Gain: ~1,100 ft | Difficulty: Moderate
After the run: Head into Cornwall-on-Hudson. Painter's Tavern has been a local staple for good reason: rotating craft taps, solid food, and a crowd that won't blink when you walk in still sweaty. Throw on your salt. tee, grab a stool at the bar, and let the post-run settle in properly.
Why do serious trail runners keep coming back to Storm King State Park?
Storm King is short, steep, and absolutely unforgiving, and that's the entire point. The Stillman Trail covers roughly 4.5 miles with over 1,200 feet of elevation gain, making it one of the most demanding climbs per mile in the entire Hudson Valley. The terrain is rocky, the exposure is real, and the views from the summit ridge, sweeping panoramas of the Hudson River, are as good as anything in the state.
Located near Cornwall-on-Hudson, about 15 miles from Chester, Storm King gets underestimated by runners who look at the mileage and assume it'll be a casual outing. It will not be a casual outing. By mile two your legs will understand the mistake, and the descent back down is technical enough to demand full attention even when you're already running on fumes.
One practical note: run it early. The parking lot fills fast on weekend mornings, and sharing that ridgeline view with a crowd of day-hikers changes the experience in a way that's hard to explain until you've had both versions.
Distance: ~4.5 miles | Elevation Gain: ~1,200 ft | Difficulty: Hard
After the run: Drive 15 minutes north to Cold Spring. It's one of the best post-run towns in the Hudson Valley, small, walkable, right on the river. Grab a beer at the Cold Spring Taproom or sit down at Riverview Restaurant and watch the Hudson move while your legs slowly figure out how to function again.
What is the Salt Outfitters Asheville Trail and Brew trip coming in 2027?
If the Hudson Valley trails have your legs and your head right, you're exactly the kind of person we built Salt Outfitters for. In 2027, we're taking a group south to Asheville, North Carolina for the Trail and Brew trip, a guided adventure weekend in the Blue Ridge Mountains.
The plan: technical singletrack in Pisgah National Forest, elevation that makes Schunemunk look like a warmup run, and post-trail hours at some of the best craft breweries in the country in one of the most celebrated trail running destinations in the Southeast. You earn it on the trail. You celebrate it in town. And you do it with a crew of people who actually understand what that means.
Details are coming together. Spots will be limited. Get on the email list at saltoutfitter.com and you'll be first to know when registration opens.
FAQ: Trail Running in the Hudson Valley
What is the easiest trail run near Chester, NY for beginners?
Black Rock Forest near Cornwall is the most accessible trail run in the area for newer trail runners. Routes around 6 miles with roughly 1,100 feet of gain offer a real trail experience without extreme technical terrain, and the near-total lack of crowds makes it a good environment to build singletrack confidence without pressure.
How long does it take to run Schunemunk Mountain?
Most trail runners complete the Jessup Trail loop on Schunemunk in 90 minutes to 2.5 hours, depending on fitness and pace. The 7.5-mile route includes around 1,600 feet of elevation gain, so expect the effort to feel significantly harder than the same distance on roads.
Is Harriman State Park good for trail running beginners?
Yes. Harriman's Pine Meadow Lake loop, around 8 miles with moderate elevation, is a strong starting point for runners new to trail running. The trails are clearly marked, the terrain is manageable throughout most of the route, and the setting delivers a genuine trail experience without throwing you into the deep end.
When is the best time of year to trail run in the Hudson Valley?
Fall, September through November, is the best season for trail running in the Hudson Valley. Temperatures are cool, foliage is at peak color, and trail surfaces are typically firm and dry. Spring can be muddy well into May, summer brings real heat and humidity, and winter requires traction devices on icy terrain.
How do I get on the list for the Salt Outfitters Asheville Trail and Brew trip in 2027?
Sign up for the Salt Outfitters email list at saltoutfitter.com. Trip details, dates, and registration will go to subscribers first. Spots will be limited, so early sign-up is the move.
The Hudson Valley trail network is genuinely world-class, and most people running roads an hour south have no idea what's up here. You've got no excuse now. Pick a trail, put in the work, and earn your salt.