This Quiet New York Town Is An Underrated Gem For 2026
Rhinebeck, New York, is a small village in the Hudson Valley in Dutchess County, about 100 miles north of New York City. The town is close enough to the city for an easy weekend away, but far enough that staying away too long can make you miss its small-town character and close-knit community. Halfway between the Catskill Mountains and the 450-million-year-old Taconic Mountains, a range of the Appalachian Mountains, Rhinebeck has about 2,600 residents. Locals enjoy history, culture, wine tasting, antiquing, and spending time outdoors.
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Rhinebeck’s Historic Heart
Before Europeans settled the area, the Rhinebeck area was home to the Sepasco band of Native Americans, who established a historic trail often referred to as the Sepasco Trail. Drawn by opportunities in the New World, Dutch settlers, including entrepreneurs, farmers, and traders, arrived in the Hudson River Valley around 1686 and purchased 2,200 acres of land from the Sepasco tribe. In 1704, one of those settlers, William Traphagen, established the Traphagen Tavern at the intersection of the King’s Highway (Route 9) and the Sepasco Trail (Market Street). The Beekman Arms Inn was added to the tavern in 1766 and has been operating ever since, becoming one of America’s oldest continuously operating inns.
During the 1980s, then-owner Charles LaForge Jr. purchased the nearby Delamater Inn. Today, the Beekman Arms and Delamater Inn is considered the heart and soul of Rhinebeck. Located in the center of the village, the hotel has long served as a focal point of community life and once hosted Franklin D. Roosevelt. The combined Beekman Arms and Delamater Inn is part of Historic Hotels of America, a program of the National Trust for Historic Preservation that recognizes historic hotels across the U.S.
Shops and Restaurants Worth Wandering In
Rhinebeck’s walkable downtown core includes East Market and Montgomery streets, where visitors can wander through independent shops. These include Oblong Books, founded in 1975 and sponsor of the White Hart Speaker Series; Rhinebeck Mercantile, which sells handpicked one-of-a-kind items for the whole family; Fig & Bella, offering textiles, pillows, and home goods; Pause Dog Boutique; and Land of Oz Toys.
Samuel’s Sweet Shop, Rhinebeck’s longest-running sweet shop, opened in 1994 as a boutique candy and coffee shop founded by a man with a love of penny candy. Thirty years later, the candy store and café is co-owned by actor and comedian Paul Rudd and Jeffrey Dean Morgan of “The Walking Dead.” Foster’s Coach House Tavern is a historic tavern and restaurant in town, originally built in 1890 as The Village Tavern. It remains a long-standing local institution serving classic American fare, including London broil, chicken Parmesan, and bone-in pork chops.
Famous Families
Rhinebeck’s character is reflected not only in its historic inns, independent shops, and cafés housed in 18th- and 19th-century buildings, but also in its ties to several well-known American families. These include the Roosevelts, whose landmark home in Hyde Park, the Home of Franklin D. Roosevelt, is about 10 miles from Rhinebeck.
The Wilderstein Historic Site is a prominent landmark in Rhinebeck. Once the home of Margaret, Daisy Suckley, Franklin Roosevelt’s cousin and confidante, the mansion is considered an important example of Victorian architecture in the Hudson Valley. The house museum offers tours of the mansion and its walking trails, along with seasonal holiday events. The Astor family, who translated early fur trade wealth into extensive New York City real estate holdings, also owned several estates in and around Rhinebeck.
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Festivals and Museums
Rhinebeck hosts several well-known annual events, including the Dutchess County Fair, which draws hundreds of thousands of visitors each August to its 140 acres of fairgrounds. The fair, dating back to 1842, combines livestock shows, rides, concessions, and exhibits, and attracts roughly half a million visitors each year. The Old Rhinebeck Aerodrome is another established Hudson Valley attraction. Founded in 1958 by an aviation enthusiast, the museum focuses on aircraft from the Pioneer era, World War I, and the Golden Age of Aviation.
Today, the site is a widely recognized destination, with more than 60 vintage aircraft, antique cars and motorcycles, and memorabilia displayed across several buildings on a rural airfield. Airshows are held regularly, with demonstrations taking place overhead.
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Communing with Nature
Ferncliff Forest is a nature preserve in Rhinebeck with 12 miles of trails for walking, hiking, mountain biking, fishing, camping, and skiing. Originally part of an estate belonging to the prominent Gilded Age Astor family, 190 acres of the sanctuary were donated to the community in 1964 by Brooke Astor, a philanthropist and the wife of Vincent Astor. Vincent Astor was the son of John Jacob Astor IV, who perished on the Titanic.
For panoramic views of the Hudson River, the Catskills, and the distant peaks of the Taconic Mountains and Berkshires, visitors can hike the one-mile trail through dense forest to the Ferncliff Forest Fire Tower.
Great Next Door Neighbors
Another aspect of life in Rhinebeck is its proximity to neighboring towns. Less than 15 minutes away, Tivoli is a 1.8 square-mile village on the eastern bank of the Hudson River with an active arts scene. The 153-acre Kaatsbaan Cultural Park hosts events ranging from poetry readings to ballets and outdoor concerts. The Tivoli Artists Gallery is home to 40 local artists working in a variety of media, with rotating monthly exhibitions. The Traghaven Whiskey Pub features an extensive selection of Irish whiskey.
Woodstock is about a 60-minute drive from Rhinebeck, passing through the Hudson Valley and the foothills of the Catskills. Known for its arts and music scene, Woodstock’s walkable Tinker Street includes long-standing shops, cafés, and live music venues, including the Colony, which dates to 1929. HappyLife Productions offers merchandise inspired by the town’s music history and festival legacy.
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Why Rhinebeck Continues to Stand Apart in the Hudson Valley
Rhinebeck is a small village in the Hudson Valley with a strong sense of history and cultural continuity. Founded by Dutch settlers and anchored by the long-standing Beekman Arms Inn, the town reflects deep American roots alongside a contemporary village life. Its walkable streets include independent shops, historic taverns, and cafés, while nearby landmarks connect Rhinebeck to families such as the Roosevelts and Astors. Seasonal events, museums, forest trails, and river views contribute to a varied local experience that continues to define Rhinebeck as it moves into 2026.
