Historical Road Trip Through the Catskills

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Update: February 2026

The winding roads of the Catskill Mountains are more than just transit routes; they are ribbons of history that tie together the rugged peaks and deep “cloves” of the northern Appalachian range. For those of us who find peace in the shadow of a ridge, these tours offer a perfect blend of high-elevation vistas and the quiet charm of valley hamlets.

The Premier Scenic Byways

If you’re planning a drive, these three routes serve as the backbone of the region’s road touring culture:

• The Catskill Mountains Scenic Byway (Route 28): Stretching 52 miles through the heart of the central Catskills, this route links the popular hub of Phoenicia with the high-elevation beauty of the High Peaks. It’s a journey through the “forever wild” Forest Preserve.
• The Mountain Cloves Scenic Byway (Route 23A & 214): Known for its dramatic “cloves” (steep mountain valleys), this route takes you through Kaaterskill Clove, where the Hudson River School of Art was born. The switchbacks near Hunter Mountain are legendary among motorcyclists and scenic drivers alike.
• The Upper Delaware Scenic Byway (Route 97): Hugging the border of New York and Pennsylvania, this 70-mile stretch follows the Delaware River. The highlight is “Hawk’s Nest,” a series of winding curves perched high above the river that offers some of the most photographed views in the Appalachian chain.

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Appalachian County Breakdown

In keeping with our focus on the mountain region, here is a breakdown of what to look for within the specific Appalachian counties of the Catskills:

Ulster County: The High Peaks & Reservoirs

This is the “gateway” to the high mountains.

• Ashokan Reservoir: The 28-mile loop around the reservoir offers unobstructed views of the High Peaks reflecting in the water.
• Phoenicia: A classic mountain town perfect for a pit stop. Don’t miss the Empire State Railway Museum to see how the rails once conquered these grades.
• Esopus Creek: Route 28 parallels this world-famous trout stream, offering plenty of pull-offs for a moment of quiet reflection by the water.

Greene County: The Great Northern Catskills

Home to the most dramatic vertical relief in the region.

• Kaaterskill Falls: Accessible just off Route 23A. It is the highest cascading waterfall in the state and a pillar of Appalachian lore.
• Five State Lookout: Located on Route 23 in East Durham, on a clear day you can see across the Hudson Valley to the mountain ranges of four other states.
• Mount Top Arboretum: A high-elevation sanctuary in Tannersville that showcases the unique flora of the Appalachian plateau.

Delaware County: The Western Highlands

Where the mountains give way to rolling pastoral beauty and river headwaters.

• Pepacton Reservoir: Route 30 offers a serene drive along the shores of this massive reservoir, with the Shavertown Bridge providing a stunning vantage point.
• Covered Bridges: This county is a treasure trove for bridge hunters, including the Fitches Bridge and the Downsville Bridge—reminders of the region’s 19th-century timber heritage.
• Roxbury: A town that feels frozen in time, featuring the historic Jay Gould Memorial Reformed Church and the summer home of naturalist John Burroughs.

Sullivan County: The River & The Arts

Focused on the southwestern slopes and the Delaware River corridor.

• Hawk’s Nest: The crown jewel of Route 97. The stone walls and tight curves offer a thrill for drivers and a breathtaking view of the river valley below.
• Bethel Woods: A short detour from the river routes takes you to the site of the 1969 Woodstock festival—a cultural landmark nestled in the Appalachian foothills.
• The Beaverkill River: Known as the birthplace of American dry-fly fishing, the roads following this river are quiet, shaded, and deeply peaceful.

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Seasonal Notes for the Road

While the Catskills are a year-round destination, autumn remains the undisputed champion for road tours. Peak foliage typically hits the higher elevations in Greene and Ulster counties by the second week of October. However, don’t sleep on late spring, when the mountain laurel and rhododendrons begin to bloom along the rocky outcrops of the Delaware Valley.