A (Holiday) Weekend in…Rhinebeck

Our favorite businesses in our favorite towns.

For much of its history Rhinebeck has been a prosperous community, benefiting from its proximity to the Hudson River and New York City. In 1686 five Dutch settlers bought 2,200 acres of land from the Sepasco Native Americans. It wasn’t until 1700 when a group of Bavarian Palatine settlers moved down from Columbia County and built homes that the village officially became Rhinebeck, named after the Rhine River of their homeland. After the Civil War, Rhinebeck attracted wealthy New Yorkers who built family estates along the banks of the river. By the early 1900’s Rhinebeck became the largest producer of violets in the world. No longer a commercial center for flower production, the agrarian, bucolic landscape continues to attract residents and second home owners. Victorian architecture has been well preserved and a walk through the residential neighborhoods offers a glimpse into the past. Where Market Street meets Montgomery Street is and has always been the center of village life and the place to begin your exploration.

  • Stay at The Beekman Arms where you can sit fireside just as guests did way back in 1704 when it was the Traphagen Tavern. If you’re truly on the hunt for a bit of history, you’ll want to reach out in advance of your visit to the Museum of Rhinebeck History or the Rhinebeck Historical Society Archives at Starr Library. Hours are limited but digital collections are accessible at any time. Enjoy a day at Wilderstein, an Italianate country home that belonged to the Suckley Family, relatives of Franklin Delano Roosevelt. There are special holiday tours. Afterwards grab a booth made from a horse stall at Foster’s Coach House, a tavern serving locals and visitors since 1890. Be sure to return in the summer for a visit to the Aerodrome!

  • Stay at the Mirabeau Inn & Spa. You’ll want to make sure you take full advantage of the spa part (hot tub, sauna, treatments), get in a yoga class or two, and have a cocktail in a bathrobe at The Aqua Terrace. Visit Zephyr, a dress shop out of a fairytale, and buy your “sweetie” some sweet and salty signature bark at Samuels. In the evening cozy up at the bar for oysters at Le Petite Bistro or a booth at Market St. for delicious Italian fare prepared with local ingredients.

  • We get it–this is a spontaneous trip and you’re looking to book something last minute. You might be able to find a cozy cabin in the woods on Airbnb. If not, see if you can grab a room at The Rhinebeck Motel. Start the day off right with a hearty breakfast at Pete’s Famous Restaurant then head swing by A.L. Stickles Five and Dime. Stock up on neco wafers, cheetah print socks and squishy stress balls. Grab lunch at Pizzeria Posto or Aba’s unless you don’t like garlic, in which case, sorry to hear that. Climb the tower at Ferncliff Forest or bring your sled to Drayton Berger Hill and prepare for an epic view and a thrilling ride! Don’t leave town without gearing up at Cabin Fever Outfitters.

  • Be sure to check out Rhinebeck’s Sinterklass Festival on December 3rd, a tradition brought by Dutch settlers over 300 years ago. Prepared to be filled with awe and wonder at the costumes, decorations and performances. Activities throughout the day lead up to the main event, the parade. Bundle up, grab a hot cocoa at Bread Alone, and explore the village. Start at Upstate Down! There’s something for everyone!

    The Wonderland of Lights is so much fun for the littles. Pack the car with kiddos and get ready to oooh and ahhh. Through December 25th, the Dutchess County Fairgrounds offers a nightly drive-thru light show. Who doesn’t love a little extra light during winter’s short days?

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