Riding Trails Near the Catskills

The Catskill Mountains are more than just a scenic backdrop for Kingston, NY; they are a playground for those who live life on two wheels. At Woodstock Harley-Davidson®, we know that for our riders, a trail isn't just a path through the woods, it is a ribbon of asphalt that challenges your skills and rewards your spirit. Whether you are leaning into a hairpin turn on a nimble Nightster™ or cruising the long sweeps of a mountain pass on a Road Glide®, the Catskills offer some of the most iconic motorcycle routes in the Northeast.

As your local authority on all things Harley-Davidson® in the Hudson Valley, we’ve put together a guide to the best Harley-Davidson® friendly routes that are open and ready for your next adventure. Before you kick up the kickstand, make sure to stop by our dealership in Kingston to browse our latest inventory or ensure your bike is peak-performing with a visit to our service department.

1. The Catskill Mountains Scenic Byway (Route 28)

Starting just minutes from our doors in Kingston, Route 28 is the essential Catskill riding experience. This is a primary state highway, meaning the road quality is exceptional and perfectly suited for the heavier frames of a Grand American Touring bike.

The Route: Follow Route 28 West from Kingston toward West Hurley and Phoenicia.
Why It’s Harley-Davidson® Friendly: The lanes are wide and the pavement is well-maintained, allowing for a smooth, confident ride even with a passenger.
The View: You’ll shadow the Esopus Creek and pass the breathtaking Ashokan Reservoir. There are several paved pull-offs where you can park your Harley-Davidson® motorcycle to grab a photo of the mountains reflecting off the water.
Status Check: Open year-round, though peak riding is from late April through the vibrant fall foliage of October.

2. The Hawks Nest (Route 97)

While technically located along the Upper Delaware Scenic Byway, the Hawks Nest is a legendary destination for any rider visiting the Woodstock Harley-Davidson® area.

The Route: A stretch of Route 97 just outside of Port Jervis.
The Experience: Known for its "snake-like" curves carved directly into the side of the cliff, this route offers dramatic views of the Delaware River far below. The stone walls lining the road provide a classic, cinematic aesthetic that complements the timeless look of a Harley-Davidson® Softail®.
Rider Tip: This is a technical ride. Ensure your brakes and tires are in top shape before attempting the switchbacks. Our service technicians at Woodstock Harley-Davidson® can perform a quick safety check to give you peace of mind.
Status Check: This route is a public highway and remains open, though it is best enjoyed on weekdays to avoid heavy tourist traffic.

3. The Mountain Clove Run (Route 23A to Route 214)

If you want to experience the true ruggedness of the mountains, the run through Kaaterskill Clove on Route 23A is a must.

The Route: Take Route 23A through Palenville and up into Tannersville, then loop back via Route 214 through Stony Clove Notch.
The Experience: This route features steep grades and tight "S" curves that will have you truly feeling the torque of your Milwaukee-Eight® engine. Stony Clove Notch (Route 214) is a narrow mountain pass where the rock walls rise steeply on both sides, creating a cool, shaded corridor even in the heat of July.
Fact Check: Route 23A is notorious for its beauty and its difficulty. Watch for pedestrians near the Kaaterskill Falls trailhead and keep an eye out for loose gravel in the early spring.
Status Check: Fully accessible for the riding season.

4. The Shawangunk Ridge (Route 44/55)

Heading south from Kingston toward New Paltz takes you to the "Gunks." This area offers a different kind of mountain beauty characterized by white quartz cliffs and expansive valley views.

The Route: Route 44/55 climbing over the ridge through Minnewaska State Park.
Harley-Davidson® Compatibility: This road was made for the "low and slow" cruising style. The hairpins at the "Trapps" bridge are famous among local riders. It’s an ideal spot to showcase the chrome of a Heritage Classic or the modern lines of a Sportster® S.
Must-Stop: The scenic overlook at the top of the ridge provides a panoramic view of the Wallkill Valley that is second to none.
Status Check: Open and popular; however, be mindful of cyclists who also frequent this mountain climb.

Preparing for Your Mountain Ride

Riding in the Catskills requires a bit more preparation than your average valley cruise. The elevation shifts and mountain micro-climates can catch an unprepared rider off guard.

Check Your Gear

The temperature can drop 10-15 degrees as you ascend into the high peaks. We recommend layering with official Harley-Davidson® riding gear. Our parts and apparel department in Kingston stocks everything from ventilated jackets for the valley heat to windproof layers for the mountain gaps.

Performance and Safety

Before tackling steep mountain descents, ensure your Harley-Davidson® motorcycle is in top mechanical condition.

Brakes: Constant downhill braking can lead to brake fade if your fluid is old or your pads are worn.
Tires: Mountain curves demand maximum grip. If your tread is getting low, visit us for a fresh set of tires specifically designed for your model.
Fluid Levels: Keep your engine running cool during those long climbs with a fresh oil change using genuine Harley-Davidson® lubricants.

Why Woodstock Harley-Davidson®?

Located at 949 NY-28 in Kingston, NY, Woodstock Harley-Davidson® is the gateway to these incredible mountain trails. We only stock and service the products you trust from the legendary Harley-Davidson® lineup.

Whether you are looking for a new CVO™ Road Glide® to tour the entire Northeast or a pre-owned Street Bob® for weekend sprints through the cloves, our team is here to help you find the perfect ride. We don't just sell bikes; we live the lifestyle. Our staff can often be found out on these very same trails, and we are always happy to share our secret spots and favorite roadside diners with our customers.

Visit Us Today

Ready to take on the Catskills?

Browse Our Inventory: Check out the latest Harley-Davidson® models online or in-person.
Schedule Service: Ensure your current bike is ready for the rigors of the mountain roads.
Join the Community: Stay tuned for our dealership-led group rides that explore these scenic byways.

The mountains are calling, and there is no better way to answer than on a Harley-Davidson® motorcycle. We'll see you on Route 28!