New Yorkers have perfected the art of the weekend escape, but the routes they follow tend to calcify into the same handful of predictable stops. Look beyond the well-trodden paths Weekend Destinations, however, and both upstate New York and the Hamptons reveal an eccentric streak that rewards the curious. For travelers who prefer upstate new york vacation rentals over hotel lobbies, these destinations offer character that no chain property can replicate.
The Catskills’ Unexpected Museums
The Catskills are famous for hiking and fall foliage, but tucked between the mountain roads are some genuinely strange cultural institutions. The Opus 40 sculpture park in Saugerties is a 6.5-acre environmental artwork carved from an abandoned bluestone quarry by one man over 37 years. Nearby, the Kaaterskill Falls, a two-tiered waterfall that inspired Hudson River School painters, still draws artists alongside hikers. In Phoenicia, the Empire State Railway Museum occupies a restored 1900 train station and hosts rides on vintage railcars through the Esopus Creek valley.
Hudson Valley’s Oddball Architecture
The Hudson Valley corridor between Beacon and Hudson has become a magnet for creative types, and the architecture reflects it. Olana, the Persian-inspired hilltop estate of painter Frederic Edwin Church, offers views of the Catskill Mountains that Church himself considered his greatest canvas. In Beacon, Dia:Beacon fills a former Nabisco box-printing factory with monumental works by artists like Richard Serra and Dan Flavin. The building itself, a 300,000-square-foot industrial shell flooded with natural light through sawtooth skylights, is as compelling as anything hanging inside.
The Hamptons Beyond the Headlines
The Hamptons carry a reputation for celebrity sightings and overpriced rose, but the eastern end of Long Island has a layered history that predates the summer social circuit by centuries. The Montauk Point Lighthouse, commissioned by George Washington in 1792, stands as the oldest lighthouse in New York State. Nearby, the Walking Dunes in Hither Hills State Park are a rare parabolic dune system where 80-foot sand hills slowly engulf the surrounding forest, burying trees that re-emerge years later as ghostly stumps. Choosing The Hamptons rentals puts you within easy reach of these natural oddities alongside the galleries and farm stands that give the area its quieter appeal.
Getting the Timing Right
Summer is the obvious season, but autumn transforms both upstate New York and the Hamptons into something quieter and arguably more beautiful Weekend Destinations. The foliage peaks in mid-October upstate, while the Hamptons enjoy an extended warm season through November, when the beaches empty out and the light turns golden and horizontal. Winter brings its own rewards: cross-country skiing in the Catskills, fireplace evenings in converted farmhouses, and the rare pleasure of having a world-class art museum nearly to yourself.
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