Where to stay
The Beekman Arms is Americas oldest operating inn (circa 1766) and the spot where Bill and Hillary Clinton welcomed guests at a soiree on the night before the wedding. Its vintage white colonial façade holds 23 comfortable rooms, from $155/night, while its sister property, The Delameter Inn, has 50 rooms in several historic buildings, from $125/night. Belvedere Mansion, a dramatically columned, circa-1900 mansion house (shown at left; courtesy of Belvedere Mansion) and guest cottages, ups the romance quotient significantly with a stunning hilltop location, views of the Hudson and the Catskill Mountains, and elegant décor featuring 19th-century French and Italian antiques, from $150/night. The Rhinecliff, a cheery yellow, fully restored 1854 property located on the Hudson about two miles from Rhinebecks town center, features original wood floors and stone fireplaces, but its nine rooms (shown below; courtesy of the Rhinecliff) have modern-chic décor, flat-screen TVs and private balconies overlooking the river, from $240.
Where to eat
Terrapin Restaurant, a cozy eatery in a former church, combines romantic ambience, a creative and eclectic menu, and terrific service. The Tavern at the Beekman Arms features a Colonial Tap Room with an open hearth, great food and wonderful wine selection. On Sundays, head for the Jazz Brunch at The Rhinecliff, served in its brasserie-style restaurant/bar. Le Petit Bistro wins raves for its wonderful French cuisine and intimate, Old World atmosphere, despite outdated décor, while Gigi Trattoria is the spot for authentic Italian fare and a great bar scene, although the ambience can be boisterous. Arielle is a newcomer serving great French-Mediterranean food in a fun, cafe atmosphere, and Sabroso is known for its delicious Latin-fusion dishes (shown at right; courtesy of Sabroso). Calico Restaurant, perhaps the tiniest French bistro in the world, is fantastic for a light lunch or très decadent desserts.
What to do
Gallery-hop at Gazen Gallery, showcasing local artists; Gallery Lodoe, specializing in Asian-inspired artwork; and Jo Aarons Gallery, for contemporary American art. History-lovers can head to nearby Hyde Park to visit Springwood, the home of Franklin Delano Roosevelt, and the gilded-age Vanderbilt Mansion with its gorgeous Formal Gardens (shown at left; courtesy of Duchess County Tourism). Hyde Park is also home to the Culinary Institute of America, where you can enjoy one of five fabulous student-staffed restaurants.
How to get there
Rhinebeck is located two hours north of New York City by car, or one hour and forty-five minutes on Amtrak, from Penn Station to Rhinecliff.