The mountain-flanked valley that inspired Hudson River School painters in the 19th century has great views and plenty to do.
A trip up the Hudson River is a trip through America’s history. The U.S. Military Academy at West Point looms on the western banks, while the eastern shore boasts the home of President Franklin Delano Roosevelt and Vanderbilt Mansion, both national parks, as well as Sing Sing state prison. (Located north of Manhattan, the prison is where the term “up the river” comes from.) Entry fees are common for many attractions, but there are plenty of free things to do.
Trivia buffs know that this storied artists’ colony nestled in the Catskill Mountains did not host the generation-defining 1969 concert that bears its name. It actually took place some 50 miles away in Bethel. But Woodstock maintains a whiff of patchouli all the same. Bohemians have been coming here for more than a century to paint, play and thumb their noses at cultural norms. Today, shops along the main street sell tie-dye clothes, groovy candles and Jimi Hendrix posters as well as fashionable shoes and pricey clothes. Good people-watching, too: Woodstock is the sort of place where gray-bearded hippies share the sidewalk with stiletto-heeled moms pushing $800 strollers.
Some of the best views of the Hudson River are from a rail bridge-turned-pedestrian walkway 212 feet (65 meters) above the water. The popular Walkway Over the Hudson, which is part of the state park system, spans 1.25 miles (2 kilometers) between Highland and Poughkeepsie. The runway-like deck looks down on a hilly section of the valley well-suited for watching the leaves turn color. It costs nothing to walk across the bridge; there is a fee for parking in the lots for the park (one on either side of the river), but free parking can often be found on nearby streets. Want a longer trek? The walkway is connected to the Hudson Valley Rail Trail on the western side and will soon be linked to the Dutchess Rail Trail on the eastern shore.
The Catskill Mountains, rising up west of the river, offer dozens of trails though pretty woods that lead to great views. Many trails are suitable for family hikes, like the roughly 2-mile (3.2-kilometer) round trip to Kaaterskill Falls near Palenville. Overlook Mountain offers some of the most panoramic views, and the climb can be coupled with a visit to Woodstock, which is just down the road. A 2.6-mile (4-kilometer) dirt road leads to a 3,140-foot (957-meter) peak that overlooks the Hudson to the east and undulating mountains all around. Ghostly ruins of old hotels are near the peak, which is topped by an old fire tower. The trailhead is across the road from a Tibetan Buddhist monastery — this is Woodstock, after all.
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A number of once-sleepy Hudson Valley towns have been gentrified over the decades thanks to an influx of second-homeowners from New York City. One of these busier small places is Rhinebeck, which cemented its status as a destination when Chelsea Clinton married at a local riverside estate in 2010. Rhinebeck is essentially a one-stoplight town with a concentration of stores and restaurants packed around the intersection. There’s a fun outdoor farmers market through Thanksgiving on Sundays. A half-hour north is the small, riverside city of Hudson, which was hit with the gentrification wave more recently. Once empty storefronts on Warren Street now host funky antique shops and the Spotty Dog Books & Ale, which, yes, really has a bar next to the bookshelves.
Rail lines run along the banks of the Hudson River from Manhattan to Albany, limiting access to the river. There are a few nice riverfront parks, though. Albany’s Corning Preserve has a fitness trail that runs along the river. The preserve is cut off from downtown Albany by tracks and an interstate, but a pedestrian bridge spans over the highway, leading to a park area with an amphitheater.