For the 50+ Traveler

Stretching nearly 150 miles from Yonkers in Westchester County to the state capital of Albany, and spanning both sides of the Hudson River, the quaint towns of the Hudson Valley are the perfect escape from the hustle and bustle of New York City.

This fertile valley is full of family farms, orchards, and vineyards focused on sustainable food and regenerative agriculture. Its scenic views and quaint settings have inspired artists and writers. And its laid-back atmosphere has delighted vacationers for generations, from the Rockefellers and Vanderbilts to everyday travelers.

Here are 10 quaint towns to visit in the Hudson Valley.

The Old Dutch Church in Sleepy Hollow.

1. Sleepy Hollow

Population: 10,100

Just 30 miles north of the Big Apple, the village of Sleepy Hollow is forever tied to Ichabod Crane thanks to Washington Irving’s The Legend of Sleepy Hollow. So begin your experience in this quaint Hudson Valley town by visiting the Old Dutch Church. It’s best to visit Sleepy Hollow in October, not just because the whole town celebrates Halloween in a big way, but because the Old Dutch Church is only open to visitors then.

Although the Headless Horseman haunted the 17th-century church’s burying ground, the author of the spooky short story is buried in the adjacent Sleepy Hollow Cemetery. When visiting Sleepy Hollow Cemetery during the fall, take an evening walking tour to wind past the graves of William Rockefeller, Andrew Carnegie, and Elizabeth Arden by the light of kerosene lanterns.

When you’re sufficiently spooked, wrap up your visit to Sleepy Hollow at Kykuit, the magnificent, 40-room Rockefeller Estate overlooking the Hudson River in Pocantico Hills.

The Blue Dolphin Diner in Katonah.

2. Katonah

Population: 2,100

Art lovers and history buffs will love the hamlet of Katonah, about 30 minutes north of Sleepy Hollow. Explore the Katonah Village Historic District with this walking tour to learn more about the century-old, beautifully maintained Queen Anne and Victorian buildings listed on the National Register of Historic Places.

If exploring makes you hungry, stop at the Blue Dolphin Diner for a taste of Italy in the heart of Katonah. Or visit The Whitlock for local flavors, from organic fruits and vegetables to craft beer and small-batch ice cream.

Halfway between this historic district and Cross River Reservoir is the Katonah Museum of Art, known as one of the best small museums in the United States. Art lovers won’t want to miss the ever-changing exhibits and attractions inside the long, rectangular building.

For a luxurious accommodation in this part of the Hudson River Valley, stay at the Bedford Post Inn. Co-owned by actor Richard Gere, this romantic, eight-room inn includes a yoga studio and two farm-to-table restaurants that range from a casual bistro to upscale fine dining. Or, stay at the historic Crabtree’s Kittle House in nearby Chappaqua.

The ruins of Bannerman Castle in Cold Spring.

3. Cold Spring

Population: 1,960

Just north of West Point, Cold Spring is home to the Hudson Highlands State Park Preserve. Covering more than 7,400 acres along the east bank of the Hudson River, the preserve is a gorgeous place to enjoy the great outdoors, especially from late spring through early fall. Admire the scenery and wildlife along the park’s hiking trails, including a section of the Appalachian Trail. To explore the park from the water, visitors can rent canoes and kayaks from Hudson River Expeditions.

For a truly unique experience at Hudson Highlands State Park, tour Bannerman Island (originally known as Pollepel Island). Home to the ruins of the Bannerman Castle, this lush isle offers truly unique views of the Hudson Valley. Note that you’ll start your visit to the island by climbing more than 70 stairs and will explore on foot, often by walking along unpaved paths and uneven surfaces.

While in Cold Spring, consider a visit to Magazzino Italian Art. In addition to gorgeous art installations, they have walking paths, and an undeniably cute family of Sardinian donkeys lives on the grounds!

Fuel up for a day of exploring Cold Spring with breakfast at Hudson Hil’s, where breakfast fare like farm-fresh eggs and stacks of pancakes is available all day. And when you’re ready to call it a day, stay at the Hudson House or Pig Hill Inn.

Jones Farm in Cornwall-On-Hudson, New York.

4. Cornwall-On-Hudson

Population: 12,700

Just across the Hudson River from Cold Spring, Cornwall-on-Hudson allows you to continue to embrace the Hudson’s Valley’s natural beauty at the Hudson Highlands Nature Museum. From frogs and fish to owls and opossums, you’ll get to meet some of the river dwellers and woodland creatures that call this area home at the museum’s Wildlife Education Center.

Foodies will enjoy a trip to Jones Farm, where guests can pick up farm-fresh produce, homemade baked goods, and gourmet foods. Prepare a picnic basket for a day of exploring the great outdoors, or grab locally sourced ingredients to whip up a meal if your accommodations include a kitchen.

If you’d rather leave the cooking to someone else, then visit Painter’s Tavern for a wide range of American cuisine. The Canterbury Brook Inn is a Swiss restaurant offering Alpine-inspired cuisine that pairs well with wines from the Finger Lakes region. And if you have a hankering for pulled pork or slowly smoked ribs, Brothers Barbecue has the best barbecue in the Hudson Valley.

The Hudson Bridge in Highland, New York.

5. Highland

Population: 5,647

One of the coolest experiences in the Hudson Valley is walking across the Hudson River. Connecting the towns of Highland and Poughkeepsie more than 200 feet above the water, the 1.3-mile-long Mid-Hudson Bridge is the world’s longest elevated pedestrian bridge. In addition to spectacular views (they’re best at sunrise and sunset), you can enjoy many discovery zones on both sides of the Hudson, including Highland Landing, the Poughkeepsie Waterfront, and Little Italy.

The home of Franklin D. Roosevelt in Hyde Park.

6. Hyde Park

Population: 20,900

One of the largest towns on this list, Hyde Park, is closely linked to Franklin D. Roosevelt, the United States’s longest-serving president. History lovers will enjoy exploring the home of Franklin D. Roosevelt as well as his presidential library and museum.

After getting your fill of history, pair the great outdoors with adorable animals at Clover Brooke Farm. Cuddle a barnyard creature, say namaste to a llama, or hike with an alpaca. (And in case you’re wondering, llamas and alpacas are two different animals.)

Pro Tip: Although you likely won’t have an alpaca as a companion, here are 10 more fantastic hikes in the Catskills.

For a great place to stay in Hyde Park, check out the Journey Inn. This bed and breakfast is just across the road from the Vanderbilt Mansion National Historic Site. Each of the seven guest rooms is decorated with a theme related to the inn’s neighbors (the Roosevelts and Vanderbilts) or beloved destinations (like Tuscany and Kyoto).

Wilderstein in Rhinebeck, New York.

7. Rhinebeck

Population: 7,780

One of the most notable sights in Rhinebeck, just 10 miles up the Hudson River from Hyde Park, is Wilderstein. This impressive three-story Queen Anne mansion, with its distinctive circular tower, was the family estate of Daisy Suckley. In addition to serving as a close confidant to FDR, Suckley bred Scottish terriers and gifted the president his beloved Fala.

In the heart of Rhinebeck’s downtown, enjoy Irish fare at Bia. Try the Irish fisherman’s stew filled with fresh-caught fish, cabbage, and potatoes served with chunks of brown bread and creamy Irish butter. And don’t leave without a nightcap of Irish coffee boozed up with a shot of Irish whiskey. Another delicious option in Rhinebeck is The Amsterdam, which serves upscale farm-to-table dishes as well as sells fine foods in its provisions market.

Apple picking at Mead Orchards in Tivoli, New York.

8. Tivoli

Population: 1,083

The residents of this village in Upstate New York enjoy saying, “i lov iT” (which is Tivoli spelled backward). And after picking your own seasonal produce at Mead Orchards, feeding the goats at Greig Farm, and enjoying a performance at Kaatsbaan Cultural Park, you’ll be doing the same!

You’ll also love the Hotel Tivoli, a quaint but contemporary century-old building in the heart of town. There are 11 guest rooms on the second and third floors and a Mediterranean-inspired farm-to-table restaurant on-site.

The Thomas Cole National Historic Site in Catskill.

9. Catskill

Population: 11,370

English artist Thomas Cole was so mesmerized by the rugged beauty of the Catskill Mountains region of the Hudson Valley that he organized a group of similarly inspired landscape artists known as the Hudson River School. Begin your visit to Catskill with a stop at the Thomas Cole National Historic Site, Cole’s home and studio. Then pair the great outdoors with awe-inspiring art by exploring nearly 20 Hudson Valley sights along the Hudson River School Art Trail that inspired the artist’s work.

While Sleepy Hollow and Tarrytown are all about the Headless Horseman, this area of the Hudson Valley embraces Washington Irving’s other popular character, Rip Van Winkle. When you’re ready for a bite to eat, head to the Rip Van Winkle Brewing Company, where you can enjoy appetizers, burgers, and entrees that pair perfectly with their craft beer.

For a unique stay in the Hudson Valley, consider the Treetopia Campground, where you’ll find everything from canvas tents to brand-new Airstream campers. See this page for other incredible glamping destinations in Upstate New York.

When you’re ready to visit the next quaint Hudson Valley town, take the Hudson River Skywalk over the Rip Van Winkle Bridge that connects Catskill to Hudson. Along the way, you’ll be treated to incredible views that will make you believe you’ve stepped into a Cole painting.

The Olana State Historic Site in Hudson, New. York.

10. Hudson

Population: 6,150

If your inner artist or architect is craving more time with the Hudson School art gang, then you won’t want to miss the Olana State Historic Site. This Moorish-style home on the banks of the Hudson River was home to Frederic Church, Thomas Cole’s star pupil.

Or embrace the region’s pastoral setting by taking a self-guided Scenic Sips tour of local wineries, breweries, cideries, and distilleries (using a designated driver, of course).

From locally sourced ingredients to Manhattans made with American whiskey, savor the area’s flavors at Wm. Farmer and Sons. Then spend the night at the Rivertown Lodge, a 27-room, independently-owned hotel that was once a movie theater.

Here are additional recommendations for a weekend in the gorgeous Hudson Valley.