Prettiest Small Towns In The Hudson Valley
The Hudson Valley rolls north from New York City for roughly 150 miles, and somewhere along the way it quietly became one of the most beautiful stretches of small-town America: all glinting river views, mountain backdrops, and Main Streets that look like film sets, several of which actually are. Weekenders pour up from the city for exactly this. Here are the prettiest small towns in the Hudson Valley, and what makes each one worth the drive.
Cold Spring
Tiny Cold Spring might be the single most photogenic village on the entire river. Its compact Main Street tumbles downhill toward the Hudson, lined with antique shops and 19th-century storefronts, and ends at a gazebo-topped bandstand with a full-frontal view of Storm King Mountain across the water. Behind town rise the Hudson Highlands, home to Breakneck Ridge, one of the most popular and most vertical day hikes in the entire Northeast. Best of all, it is an easy, car-free day trip: the train from Manhattan drops you a two-minute walk from Main Street.
Kingston
Kingston has a genuine claim to fame: it was the very first capital of New York State, back in 1777, right up until the British burned it that same year. Today its Stockade District is a rare, still-lived-in pocket of 17th- and 18th-century Dutch stone houses, perfect for an afternoon wander, while down the hill the Rondout waterfront hums with restaurants, sailboats, and maritime history where Rondout Creek meets the Hudson. That's two distinct historic neighborhoods in one small city, with plenty to eat in between.
Hudson
Once a hard-working whaling and industrial port, the little city of Hudson has reinvented itself as the valley's antiques-and-design capital. Warren Street runs for about a mile straight up from the river, and it is wall-to-wall with antique dealers, art galleries, and beautifully restored Federal and Victorian buildings, arguably the best-preserved streetscape of its era anywhere in the region. It is small enough to stroll end to end, and dense enough to swallow a whole afternoon whole.
Tarrytown
Down in Westchester, where the Hudson balloons out into the broad Tappan Zee, Tarrytown delivers river views, a walkable village, and a hefty dose of literary history. This is Washington Irving country: the author's riverside home, Sunnyside, sits just south of town, and the famously spooky village of Sleepy Hollow, of Headless Horseman fame, is right next door. Grand estates like the Gothic Revival mansion Lyndhurst and the Rockefellers' Kykuit dot the hills above the water. It is history, scenery, and a great Main Street all rolled into one easy day trip from the city.
Woodstock
Yes, that Woodstock, more or less. The famous 1969 festival actually took place about an hour away, but it borrowed the town's name because Woodstock had already been a thriving arts colony since the early 1900s. Set against the Catskill Mountains, its Tinker Street is a happy tangle of galleries, record shops, and tie-dye that never entirely left the 1960s, and the mountain scenery wrapped around it is the real headliner. It is, proudly and without apology, exactly as bohemian as you are hoping it will be.
New Paltz
New Paltz pairs a buzzy little college-town Main Street with scenery that genuinely stops you in your tracks. Its Historic Huguenot Street preserves original stone houses dating to the early 1700s, making it one of the oldest streets in America. Just to the west, the pale cliffs of the Shawangunk Ridge and the storied Mohonk Mountain House pull in hikers and rock climbers from all over the country. Very few towns this small come with a backdrop quite this dramatic.
Saugerties
Saugerties flies a little under the radar, which is a big part of its appeal. Its walkable village is loaded with antique shops and galleries, but the real showstopper sits at the water's edge: the Saugerties Lighthouse, an 1869 beacon at the mouth of Esopus Creek that you reach by a half-mile nature trail, and can even book for an overnight stay as a bed-and-breakfast. Waking up in a working lighthouse on the Hudson is about as memorable as a weekend gets. From a riverside bandstand in Cold Spring to a lighthouse you can sleep in, the valley's small towns pack an outsized amount of beauty into a very short drive, so pick any one and you will be plotting your return before you have even left.
