Pack your car and head for the Catskills! With historic sites and iconic cultural locations, discover the history of the region and enjoy breathtaking views during a road trip through the mountains and countryside of the Catskills. Due to COVID-19, some of the following places may be closed—check the county websites prior to your trip.
Stop 1: Greene County
Begin in the Great Northern Catskills of Greene County, the northernmost region in the Catskills. The legend of Washington Irving’s Rip Van Winkle comes to life! Make a stop to play a round at one (or more!) of the nine golf courses on the Rip Van Winkle Golf Trail, hike to a sculpture of Rip Van Winkle on Hunter Mountain, and sample locally made craft beverages at the annual Rip Van Winkle Wine, Brew, & Beverage Festival.
Next, visit Catskill to see the Thomas Cole National Historic Site, featuring the former home and studio of artist Thomas Cole—you’ll see how the beauty of the surrounding landscape inspired his art.
Stop 2: Delaware County
Drive to the nearby Great Western Catskills of Delaware County, to see a working mill at the Hanford Mills Museum in East Meredith. On the National and New York State Registers of Historic Places, Hanford Mills, began as a sawmill in the 1840s, and developed into a feed mill, grist mill, and more!
Then, travel further south to Delhi to see the historic Gideon Frisbee House, built in 1797. The house—which is now the location of the Delaware County Historical Society—is known as the “Birthplace of Delaware County” because it was where local government officials met to form the county.
Stop 3: Sullivan County
Head to the Sullivan Catskills to see the former site of the 1969 Woodstock Music Festival, located on the grounds of the Bethel Woods Center for the Arts in Bethel. See where the main stage and festival field were located as you explore the property. While you’re there, check out the Museum at Bethel Woods to see exhibitions highlighting the historic three-day festival, along with those who attended.
Next, drive approximately 15 minutes to Stone Arch Bridge Historical Park in Kenoza Lake to stretch your legs. The bridge, built in 1880 and restored in 1980-81, features three beautiful stone arches and is located in a 20-acre park. There are several other covered bridges worth checking out that are located throughout Sullivan County, including the Halls Mills Covered Bridge in Claryville and the Livingston Manor Covered Bridge Park in Livingston Manor.
While you’re in Livingston Manor, make a stop at the Catskill Fly Fishing Center and Museum to experience the history of fly fishing in the Catskills. Known as the birthplace of American dry fly fishing, the Catskills boast several rivers that are perfect for enjoying the sport.
Stop 4: Ulster County
Visit Ulster County, the southernmost region of the Catskills, to find a variety of significant historical locations. Begin by learning about the Catskill Mountain Railroad at the Empire State Railway Museum in Phoenicia. While you’re in Phoenicia, explore along the Ulster & Delaware County Railroad with Rail Explorers—offering rail biking tours along the Esopus Creek.
Make your way to the Ashokan Rail Trail, which is a public trail that spans 11.5 miles along the Ashokan Reservoir. Start on the trail at any of the three trailheads—Woodstock Dike Trailhead in West Hurley, Ashokan Station Trailhead in Shokan, and Boiceville Bridge Trailhead in Boiceville.
Whether you’re a history buff or a casual traveler, a road trip in the Catskills offers a unique look into the past while celebrating the excitement of today.