One of the great joys of living in the Tuxedo Park area is the unparalleled access to unspoiled nature right outside your door. Whether you’re seeking a quick, rewarding workout, an all-day wilderness escape, a jaunt into the forest for meditation or forest bathing can be restorative. Harriman and Sterling Forest State Parks offer hundreds of miles of well documented and maintained hiking trails fit for a lifetime of outdoor activity and recreation.
To help you get started, I’ve compiled four favorite local day hikes—from rewarding scrambles to gentle mountain climbs—all conveniently located near the Hamlet of Tuxedo. Please note, these trails are challenging and not “ADA accessible style” but we will in the future post about area trails that are “accessible”.
1. Claudius Smith’s Den (Harriman State Park)
Starting Point: Hamlet of Tuxedo, NY, Grove Dr. – take Red Blazed “RD” to Red Blazed “Tuxedo-Mt. Ivy” trails. There is no parking in the East Village neighborhood of Tuxedo, so please park at the Metro North Commuter lot in Tuxedo. This is an out and back hike, not a loop.
Prepare for an invigorating ascent that rewards you with one of the most remarkable vantage points in the area. Beginning in Tuxedo’s “East Village” on Grove Drive, the trailhead immediately greets you with a steep, challenging climb heading east into Harriman State Park.
Once you reach the initial plateau, pause to take in the unrivaled, panoramic views over the entire Hamlet of Tuxedo. A second, intense incline leads you up to the historic Claudius Smith’s Den, a legendary cave once used by a Revolutionary War-era outlaw. The final segment involves a fun, rock-scramble style climb that takes you directly on top of the den’s outcrop, providing breathtaking vistas across Southern Orange County, with views that extend all the way into Northern New Jersey.
“Claudius Smith’s Den”, Photo by Jacob Matthews © 2025
2. Doris Duke Loop Trail (Sterling Forest State Park)
Starting Point: North of the Hamlet, Benjamin Meadow Rd, near the Renaissance Faire Grounds. Dedicated parking on site, then, take the white-blazed “DD” loop trail. This is a loop hike.
Often referred to as Sterling Forest’s hidden jewel, the Doris Duke Loop Trail is a beautifully maintained, yet lesser-known, route that offers both serenity and stunning payoff. The 2-3 hour moderate loop traverses the Doris Duke Preserve area.
If you choose the northerly (counter-clockwise) direction, you’ll start with a few moderate inclines before traversing along the edge of a medium-sized pond area. The trail then leads up to high mountain crests where, on a clear day, you can catch spectacular long-distance glimpses of the New York City skyline! Be sure to stop for a rejuvenating picnic on the large, bald glacial rock outcrops at the loop’s highest elevation. While some sections are flat and gentle, come prepared for portions that require deft footwork and sturdy hiking boots.
“Doris Duke Loop Trail”, Photo by Jacob Matthews © 2022
3. Furnace Loop Hike (Sterling Forest State Park)
Starting Point: North of Southfields, Town of Tuxedo. Best parking is across from the trail on the side street just off Orange Turnpike. Take the red blazed “FL” Trail off of Old Orange Turnpike. This is a loop hike.
For the hiker who loves history mixed with a good, challenging workout, the Furnace Loop is a fantastic option. This is a relatively short hike that packs a punch with several very steep uphill and downhill sections, including rock scrambles set in steep inclines.
Hiking counter-clockwise, you’ll cross a scenic wooden footbridge over a large creek before encountering the impressive stone furnace structure that historically produced iron—a fascinating glimpse into the region’s industrial past. A peaceful pond about halfway through the journey provides a perfect spot to rest and refuel before the exhilarating tail end of the hike, which includes a controlled rock scramble down a steep slope. No climbing gear needed, but you’ll want proper footwear for this section!
“Ephemeral Flower”, Photo by Jacob Matthews © 2022
4. Wildcat Mountain (Sterling Forest State Park)
Starting Point: Park & Ride Lot just north of the Hamlet of Tuxedo at Rts 17 & 17a Take the white blazed “WM” trail. This is an out and back hike, not a loop.
If you’re looking for a short hike combined with unique topography , Wildcat Mountain is your perfect choice. This is not a loop hike, so prepare for “out and back” method, hike in as far as you want or just enough – about 30 minutes – to get to the Wildcate lookout. From the north end of the lot, a gentle slope welcomes you onto the Wildcat Trail, leading you to the summit in approximately 30 minutes.
At the top, you’ll enjoy sweeping views over the central and eastern portion of Tuxedo, looking south and east toward Harriman State Park. This vantage point offers a unique perspective on the narrow valley corridor that forms much of the Town of Tuxedo. From here, you can observe the “veins of the town” snaking through the valley: the Ramapo River, the New York State Thruway, the Port Jervis line of the Metro North Train, and Route 17 highway. The bald-faced glacial rock outcrops at the edge of Wildcat Mountain are the ideal spot for that must-have scenic selfie and a quick snack!
“View from Wildcat Mountain”, Photo by Jacob Matthews © 2022
Local Hiking Resources and Safety Tips
The Harriman State Park and Sterling Forest State Park areas are well-maintained, but preparation is key to a safe and enjoyable outing.
- Check Park Websites and Socials Before You Go: Always consult park websites and socials prior to hiking for any closures, warnings, or seasonal changes (e.g., hunting seasons).
- The Buddy System: Inform a family member or friend of your chosen trail, your estimated start time, and your expected return time. Better yet, is always to hike with a partner or small group.
- The Essentials: Pack plenty of water, bug spray, sun-block, sunglasses, and a hat. Bring quick snacks (granola, nuts) and a small first aid kit. A lightweight, extra dry-wicking clothing layer is always a wise addition.
- Navigate Smart: While a charged cell phone is essential with state park maps or apps downloaded, signal strength can be spotty. Bring a printed trail map available from the NY/NJ Trail Conference or local retailers like Dottie Audrey’s.
- Gear Check: Sturdy hiking / trail runners or boots are mandatory, and hiking poles are always helpful on steep inclines and descents.
- Tick Check: Perform a thorough tick check immediately upon returning home.