This Small Town in New York Has the Oldest Continuously Operated Inn in the U.S. and a Charming Holiday Celebration Honoring Santa

Rhinebeck, a once-sleepy New York town, now has hip new hotels, cool restaurants, and fun seasonal festivals.

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Rhinebeck is a tale of two towns: part historical colonial village, part modern-day destination. Over the past few decades, this quintessential small town in New York’s Hudson Valley has found a way to comfortably straddle both the old and the new, and many are taking notice.

Historically, Rhinebeck is on solid ground. Its most well-known inn, Beekman Arms, predates the founding of the United States and boasts a guest roster that includes George Washington, Aaron Burr, Franklin Delano Roosevelt, and a long list of other notable figures. The town’s Hudson River Historic District, one of the largest in the country, includes more than 40 riverfront estates. Yet, despite its reputation as a historical hot spot, the town has steadily evolved.

Rhinebeck hit many people’s radar when Chelsea Clinton tied the knot here in 2010. Since then, the area has welcomed Mirbeau Inn & Spa, the Omega Institute holistic retreat center, Habitas-on-Hudson, and an influx of new restaurants. Soon, Soho House will debut Grasmere House, a 250-acre countryside retreat that will include a wellness facility and spa.

Josiah Brown, a New York State travel expert known as The New York Sherpa, is a resident of upstate New York and knows Rhinebeck well. He spoke with Travel + Leisure about the old, the new, and the importance of balancing between the two. “Rhinebeck is happily sitting somewhere between the colonial vibe and the health and wellness vibe,” Brown says. “When people poured out of Manhattan during the pandemic, many headed to the Hudson Valley.” With all the new life that has been breathed into this once-sleepy town, Brown says, “Rhinebeck is definitely a place I confidently recommend.”

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Rhinebeck, New York

• Opened in 1704 as a traveler’s inn, Beekman Arms is believed to be the country’s oldest continuously operated inn.
• Mirbeau Inn & Spa, Rhinebeck’s most upscale accommodations, opened in 2019 and, along with the Omega Institute, brought a new health and wellness focus to the town.
• The Fisher Center at Bard College features classical, choral, and orchestral performances, as well as presentations open to the public.
• The annual Sinterklaas Festival, named in honor of Dutch Christmas, is a one-day event with activities and performances that take place around town.
• The family-friendly Old Rhinebeck Aerodrome museum houses an antique aircraft dating back to World War I, plus visitors can attend one of its impressive air shows on summer and fall weekends.

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Best Hotels and Resorts

Mirbeau Inn & Spa Rhinebeck

Mirbeau’s 2019 debut may have been diminished by the lockdown, but it has since established itself as a standout in the Hudson Valley. “Mirbeau is an impressive, large boutique property right in the center of town, and that will help buoy Rhinebeck in the future” Brown says.“ There’s also a 12,000-square-foot spa.

Architectural Wonder in the Woods

This rental, included in Airbnb’s 2022 most wish-listed properties, is located just outside of town and sits on 30 preserved acres. The geometric structure is solar-powered, but there’s also a wood-burning stove for comfort during the cooler seasons.

Beekman Arms & Delamater Inn

Beekman Arms, with its wide-plank floors and stone hearth, packs a solid historical punch, as it’s believed to be the country’s oldest continuously operated inn. Plus, rumor has it the argument between Aaron Burr and Alexander Hamilton started in the tavern here. And although it has been modernized, it retains its colonial Americana atmosphere.

Habitas-on-Hudson

Just outside the town of Rhinebeck, Habitas-on-Hudson is the first U.S.-based property for this hip, cool brand, and T+L got a first look inside when it opened at the end of 2022. Inside, the 30-room hotel is youthful and energetic, while the exterior screams charming country estate.

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Best Things to Do 

Old Rhinebeck Aerodrome Show

According to Brown, this museum of antique aircraft is not to be missed. “The seasonal family air show is wildly entertaining,” he says. The museum includes 60 vintage aircraft, automobiles, and motorcycles. Family-friendly air shows take place on weekends from mid-June through mid-October.

Dutchess County Fairgrounds

Rhinebeck has the good fortune of being home to the Dutchess County Fairgrounds, which offers some of the best fairground programming in the state, Brown says. “It’s known for its well-curated, well-attended events,” he adds. This includes an antique show, a wine and food festival, and, of course, the annual county fair.

Wilderstein Historic Site

If timed right, visitors can tour this Queen Anne-style mansion, once home to the wealthy Margaret Suckley (cousin to Franklin D. Roosevelt). The home has been restored and retains an impressive collection of paintings, books, photos, letters, furniture, and more.

Sinterklaas Festival Day

Rhinebeck transforms into a Hallmark-worthy Christmas town each December during its annual Sinterklaas Festival Day. Events and workshops take place throughout the village and the day culminates with the Children’s Starlight Parade, led by Sinterklaas (Santa) himself.

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Best Shopping

Samuel’s Sweet Shop

Actors Paul Rudd, Jeffrey Dean Morgan, and Hilarie Burton are among the owners of this candy shop in the center of the village. They were part of a small group of investors who saved the store from closing nearly 10 years ago.

Rhinebeck Mercantile

Once a department store, this shop relaunched in early 2023 as Rhinebeck Mercantile. It’s located on Market Street in a historic brick building built in the late 19th century and offers clothing, accessories, gifts, and more.

Beekman Arms Antique Market

Tucked away in a two-story barn, this emporium draws antiquaries from around the Hudson Valley. It’s easy to lose track of time perusing its many high-end antiques.

Oblong Books

Oblong Books has been attracting locals and visitors alike since opening in 1975. The independent bookstore regularly hosts author signings, readings, and other community-focused events.

Best Nightlife

Fisher Center

Located at Bard College, about 10 miles away, the Fisher Center hosts chamber, choral, and orchestral performances, as well as other arts programming and discussions.

Watering Holes Around Town

There are plenty of spots around Rhinebeck to grab a drink when the later hours roll around. These include Foster’s Coach House Tavern (a local favorite), The Kroeg, and RhineCellar, a speakeasy-like cocktail lounge located in the basement of the Rhinebeck Hardware Company building.

The Tavern at Beekman Arms

For anyone wanting to soak up Rhinebeck’s colonial past, Brown insists on a stop at this historical tavern. “It feels like a place you would have ordered a beer 200 years ago,” he says. The Beekman also offers live music in the summer months.

Best Restaurants

Gigi Trattoria

“Gigi’s is considered among the Mount Rushmore of dining choices in Rhinebeck,” Brown shared with T+L. The menu focuses primarily on Mediterranean cuisine — both rustic and sophisticated — and the Skizza (a skinny pizza) is a must.

Terrapin

Known for its farm-to-table cuisine, Terrapin is recommended by many, including Brown. “Terrapin is an iconic dining option, in an old church, with a locally loved chefs,” he says.

Bia

Another recommendation from Brown, Bia brings the Irish Bistro scene to Rhinebeck. The menu includes Irish favorites, from fish and chips and lamb shoulder braised in Irish stout to treacle brown bread.

Le Petit Bistro

Brown also recommends Le Petit Bistro, a French restaurant that procures locally sourced and foraged produce and butchers its meat in house. Brunch includes traditional French cuisine, like crepes and quiche, and seafood is a highlight at dinner, especially the raw oyster bar.

Culinary Institute of America

In nearby Hyde Park (about 20 minutes south), a meal at the Culinary Institute is not to be missed. Brown suggests finding The Egg, the student dining space where future chefs crank out sophisticated food and the public can enjoy a gourmet meal for less than $20.

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Best Time to Visit

Like most of New York state, there may be no better time to visit than autumn, when the foliage is spectacular and the crowds are fewer. Summer brings the opportunity to attend the Dutchess County Fair and soak up the vibrant street scene. The town’s Sinterklaas Festival Day and drive-thru holiday light show (The Wonderland of Lights) at the fairgrounds make winter a solid — albeit chilly — option as well.

How to Get There

It’s a relatively direct drive from Manhattan to Rhinebeck (about a two hours, give or take), but anyone coming from Manhattan should take traffic into consideration, especially during peak seasons. For a more leisurely journey, opt for the train to Rhinecliff, about 15 minutes from town. If you’re arriving by plane and want to avoid the New York City airports, Albany is closer, with a drive time of about 1.5 hours. Visitors can also opt to arrive at an even closer regional airport, like Newburgh or White Plains.

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