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Stretching from New York City up to Albany, the Hudson Valley is a charming region of New York State that promises breathtaking views of the Hudson River and a variety of historical landmarks to explore. The array of wineries, state parks, and antique shops gives the valley a classic Northeast feel, making it the perfect getaway to escape the city’s summertime chaos. As an added bonus, the farthest part of the Hudson Valley is only around a three-hour drive from New York City. Keep reading to discover which 10 Hudson Valley towns make the perfect summer vacation spots.
The village of Sleepy Hollow is a lively community despite its name. Located just 25 miles north of Manhattan, the village is well known for its Headless Horseman lore that was born from Washington Irving’s 1820 tale The Legend of Sleepy Hollow. Irving was inspired by the village’s quaint beauty when he visited a friend in Tarrytown, and his infamous story became the reason the village was renamed Sleepy Hollow in the nineties.
Because of the village’s connection to Irving’s spooky legend, visitors can enjoy many activities catered to the legend, including guided tours of the cemetery mentioned in the book. Interested in diving deeper? Come back during October for access to the Old Dutch Church when Sleepy Hollow dedicates the entire month to all things Halloween. If you aren’t interested in the lore, however, Sleepy Hollow has many other treats to enjoy as well. The award-winning TaSH Farmer’s Market is located on the border of Sleepy Hollow and Tarrytown. Visitors can try out local cheeses, fresh produce, and artisan baked goods. Then, after you leave, head to Horan’s Landing for some kayaking or maybe a jazz concert. Check out the nearby Sleepy Hollow Lighthouse as you stroll down the scenic RiverWalk, and grab a bite at Hudson Anchor restaurant to finish off the day.
Katonah, New York is full of upscale Northeast charm, complete with both Victorian homes and colonials. Once the home of Martha Stewart and Ralph Lauren, and right around the corner from where Blake Lively and Ryan Reynolds currently live, this small town is a beautiful place to spend time away from the city. This Hudson Valley town detests chain restaurants and stores, meaning you won’t find a Starbucks on any corner. Instead, Katonah’s downtown is alive with independent boutiques and coffee shops such as Majestic Hudson Lifestyle Boutique or Joe’s Coffee and Books. A great spot for breakfast and well-known in the Katonah community is the Katonah Reading Room, where guests can lavish in pastries galore and pick out a new book.
Getting away from the picturesque downtown you will find Muscoot Farm where visitors can pet the animals, John Jay Homestead which is open for tours, and the Honey Maple Grove Lodge where visitors can spend the night in the woodsy confines of the forest.
From downtown to the outskirts, Cold Spring is a town with a plethora of things to see and do. This Hudson Valley town is known for its many antique shops lining Main Street where shoppers can get lost window shopping for hours. One of the most infamous stops, however, is Cold Spring Antique Center with every gadget or gizmo visitors could ever ask for.
Those looking for the perfect river view should head over to Dockside Park or the West Point Foundry Preserve where they can walk the river or tackle one of its many hiking trails. When you get hungry, don’t miss the Riverview, which, unsurprisingly, allows guests to dine while viewing the dazzling river. A more budget-friendly and unique option is Cold Spring Depot, which serves American fare from a converted 1893 train depot. Anyone looking for an overnight stay in Cold Springs should look no further than the Hudson House River Inn. Built in 1832 right by the water complete with an old tavern, this sleep spot is the cherry on top as a historic place to stay in the Hudson Valley.
As opposed to many smaller towns on this list, most people on the East Coast have likely heard of Poughkeepsie or its city counterpart. Poughkeepsie is a college town, home to the beautiful campuses of Vassar and Marist. The town has a unique variety of things to do, from visiting the historic Locust Grove Estate to walking the world’s longest elevated pedestrian bridge, the Walkway, over the Hudson River.
If you get thirsty head to the Mill House Brewing Company, which serves high quality and classy pub food and local beer. Much like many restaurants in Poughkeepsie that have been converted from old factories, the Mill House Brewing Company used to be an actual running mill. Just under thirty minutes away from Poughkeepsie is a unique spot to spend the night in New Paltz called Mohonk Mountain House. Considered a Victorian castle resort, guests can step back in time while enjoying finer things like heated swimming pools and four-poster beds.
Tivoli is the smallest town on this list with a population barely surpassing 1,000. Although not as glamorous as its namesake in Rome, Tivoli is a beautiful, quaint Hudson Valley town that charms each of its visitors. Rows of wood-trimmed Victorians, an art gallery, and a whiskey bar make up much of the town, but there is more than what meets the eye in Tivoli.
Coined by a former mayor in the seventies, Tivoli backward reads “i-lov-it,” and visitors and residents alike will surely agree. Check out Tivoli’s infamous Fortune’s Ice Cream, with a range of flavors as you’ve never seen, including mulberry and leaf, rosewater saffron pistachio, and corn blueberry. Visitors can also go horseback riding at Panorama Farm, or visit nearby Bard College. Then finish off your stay in Tivoli with a trip to GioBatta Alimentari, a well-known Italian restaurant run by award-winning chef Francesco Buitoni, ancestor of the creators of the Buitoni pasta brand. An even more shocking find in Tivoli is Traghaven’s Pub. At this tiny pub visitors will find the largest selection of Irish whiskey in the entire United States. All-in-all, those looking to forego city life for a small-town getaway should consider Tivoli near the top of their list.
Not to be confused with the Catskill Mountains, Catskill is also a village in the Hudson Valley. This picture-perfect town is embedded with natural beauty and a vibrant downtown. Catskill’s mountain and river views are considered to be an artist’s dream and once served as inspiration for famous painter Thomas Cole, whose house in Catskill is still visitable today (and you can visit!).
Historic Main Street is lined with old shops like the Magpie Bookshop, Sister Salvage, and Spike’s Record Rack, making this town a perfect getaway for those in search of a comforting and quiet place to escape city life. Walk over the Hudson River on the Skywalk, connected to the Rip Van Winkle Bridge. Then, when you work up an appetite, head over to either Left Bank Ciders or Crossroads Brewing Company for some local drinks and food. Better yet, check both joints out as they are within a five-minute walk of each other. Spend the night in a luxury cabin at Pinewood Lodge, and embrace the natural world around you in Catskill.
Referred to as “a gilded age getaway with a friendly vibe” by The New York Times, Hyde Park is a can’t-miss spot in the Hudson Valley. Originally created as a way for wealthy city dwellers to escape from the city, Hyde Park is still much of that today. For those looking to step back in time and make some historical stops, former president Franklin D. Roosevelt once lived in Hyde Park, and his library and house are now a museum open to the public. The Vanderbilt Mansion is another great option as a chance to explore the ornate architectural beauty of the aristocratic home, and tickets are only $10.
Hyde Park also has a comfy drive-in to complete its classic American feel, as well as the Eveready Diner or the classier American Bounty Restaurant. For those interested in taking a drive to explore more nearby historical American culture, thirty minutes away in New Paltz is the Historic Huguenot Street, where visitors can uncover 300 years of American history.
The peaceful village of Cornwall-on-Hudson is the perfect getaway for anyone looking to immerse themselves in nature. Under a two-hour drive from the city, this Hudson Valley town boasts any outdoor activity you could want. Storm King State Park has the perfect Hudson River backdrop for swimming, hiking, boating, or golfing. They even rent both cottages and cabins for campers who don’t want to sleep in a tent.
Cornwall-on-Hudson is also home to Jones Farm, a beautiful farm framed by mountain views where visitors can sample all the farm has to offer including fresh vegetables and homemade baked goods made from scratch. There are also horses and other animals to feed on the property. Visitors can even get a tarot reading at local Brid’s Closet, or check out some local restaurants like Pepettini for Italian food, or the Rock Wall Pub and Grill for some more down-home eating.
The town of Millbrook is a small but bustling community, with many amenities that make it a golden weekend-getaway destination. Millbrook Vineyards and Winery is a classy, upscale Hudson Valley find. Visitors can enjoy live music and gorgeous views with their wine amidst the winery’s elegance. Millbrook also has a weekly farmers market on Saturdays to check out local goodies and art. A 10-minute drive from the town center is Lilymoore Alpaca Farm, where anyone looking to connect with their inner wild-child can befriend some of these fluffy animals, or try out MisFit Farm for horseback riding. Some of the best restaurants in town are Millbrook Cafe and Barbaro, located in Millbrook’s historic district.
Millbrook also has many unique locations to check out such as Wing’s Castle. A modern castle tucked into the forest where guests can stay the night in enchanting luxury with a swimming pool and winery on-premises, this is the perfect spot to hide away and recharge. Also located in Millbrook is the spot where the abandoned Bennet School for Girls once stood. Built in the early 20th century but abandoned since the seventies, this former girls’ school was a daunting spot known for paranormal activity that once drew the interests of explorers from all over. Sadly, however, demolition of the old school began in 2022 and there have been few plans for what to do with the supposedly haunted land since.
The biggest and likely most well-known town on this list is Saratoga Springs, located three and a half hours from New York City. While the busy town may be known for the Saratoga Racetrack and National Museum of Racing and Hall of Fame, it also has plenty more to offer. Visitors can easily make a weekend trip out of this Hudson Valley town full of great places to stay, eat, and explore.
For example, hop on a boat and take the Adirondack Cruise and Charter, or get spooked on the Haunted Saratoga Ghost Tour. Those looking for a more relaxing weekend, however, can sit back at Gideon Putnam Resort and Spa, or drink the day away at the Saratoga Winery. Shoppers will be endlessly occupied with the shops along the main streets or with the Saratoga Marketplace, an upscale indoor mall with many charming shops. Grab a bite to eat at the ritzy 15 Church to take on the luxurious feel of Saratoga Springs. Then, stay at The Inn at Saratoga for some local historical comfort to pull it all together.
Next, check out these charming towns in the Catskill Mountains for a summer getaway!
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