Route From Catskill, follow New York State Route 23 West to Prattsville. Backtrack Route 23 East to State Route 23A East through the Catskill Park. When Route 23A East ends, follow U.S. Route 9W North to Route 23 East. Proceed across the Rip Van Winkle Bridge (toll), then turn right on State Route 9G South to the left-hand entrance for Olana State Historic Site.
"Welcome to the land of Rip Van Winkle," reads a sign that greets motorists headed west on Route 23 toward the looming mountain skyline. It was in these ancient, gray sandstone peaks, of course, that Washington Irving's likable character observed strange beings playing at ninepins, quaffed their liquor, and then slept for a night that lasted twenty years. Storytellers and artists elevated these misty hills sheathed in boreal forests to mythological status long before the region became an accessible and popular vacationland. The legendary scenes captured on canvas and recorded in fables spring to life as you follow the curvy path of this skyward drive.
In East Windham, be sure to pull off Route 23 at Point Lookout. On clear days, this overlook beside the dramatically situated Point Lookout Mountain Inn affords views of five states. As Route 23 continues to climb, you'll enter the Catskill Park, a 700,000-acre area (almost as large as Rhode Island) composed of private and public lands in four counties. Since the park was created in 1885, the state's holdings, protected within the Catskill Forest Preserve, have expanded from 34,000 to nearly 300,000 acres. With ninety-eight peaks surpassing three thousand feet, the Catskills are one of New York's most popular winter destinations; Windham, home to the Windham Mountain ski area, is the first of several cheery ski towns you'll encounter.
As you approach Prattsville, you'll see Pratt Rocks, one of the state's quirkiest attractions. Zadock Pratt, who came to the Catskills as a small boy, labored and scrimped until he could afford to open a tannery on the Schoharie Creek, taking advantage of the abundance of hemlock bark, essential to the leather-making process. Within twenty years, he'd amassed a fortune, built an entire town, opened a bank where he minted his own money, and won a seat in Congress. According to local lore, when a panhandling stonecutter wandered through in 1843, Pratt gave him fifty cents to carve his profile on a mountain ledge. Pleased with the result, he commissioned his entire life story chiseled into the cliff face. Visitors who climb the serpentine inclines at Pratt Rocks will see a horse, a hemlock, and other symbols, including Pratt's coat of arms and motto: "Do Well and Doubt Not." What began as a monument to vanity became a memorial to Pratt's only son, George, a Civil War colonel, whose bust was added to the five-hundred-foot rock wall after he died at the Battle of Manassas. Without an heir to his empire, Pratt isn't remembered far beyond the boundaries of the town he transformed, but in Prattsville, where his 1829 home is now the Zadock Pratt Museum, he remains a legend.
Next Page: Continue the Catskill Mountains Drive