Romantic Weekend Getaway in the Hudson Valley's Dutchess County

  • Distance from New York City: 85 miles
  • Best time: June to October
  • Best for: RomanticFood and WineShopping

If you're looking to slip back in history while dining on contemporary fare by America's rising culinary stars, your appetite for both will be easily satisfied during a weekend in scenic Dutchess County. Stretched along the eastern side of the Hudson River Valley, and home to charming towns such as Rhinebeck, Red Hook, and Millbrook, this pastoral playground is so alluring it famously played host to First Daughter Chelsea Clinton's wedding. Rhinebeck alone has 437 National Historic Register sites, and both it and its neighboring hamlets are full of atmospheric old inns and antiques markets, as well as the childhood home of our 32nd president, Franklin Delano Roosevelt. It's also the headquarters of the CIA—no, not the spy agency but rather the Culinary Institute of America, training ground of many of America's best chefs. And these are only a few reasons to dig into the Hudson Valley's offerings. Here's how to savor an entire weekend. – By Donna Heiderstadt


Dutchess County Cheat Sheet

View a printable list of all sights, restaurants, entertainment, and hotels from this itinerary. View

1 Wind down before you even arrive with a bit of late-afternoon wine tasting at the Millbrook Winery, located in a renovated dairy barn at the peak of a vine-covered hill. There, you can sample wines from the vines you passed on the way in.

2 Meander along Rhinebeck's main streets (E. Market Street and Montgomery Street), which are lined with art galleries and shopping boutiques. We recommend stopping into Winter Sun/Summer Moon for eclectic jewelry, clothing, and home décor; Paper Trail for artsy gifts and accessories; and EB's Hudson Valley Finds for locally made accessories and homewares.

3 Stroll a few doors down on Montgomery Street to dine at Terrapin. Located in the circa-1825 restored First Baptist Church, the restaurant highlights chef-owner Josh Kroner's French- and Asian-influenced modern American cuisine in both a dramatic dining room and the cozier and more casual bistro. Offerings range from tasty tapas (gingery pot stickers) and creative appetizers (macadamia nut-crusted calamari) to large plates like fried chicken and collard greens or beef short ribs over mashed potatoes.


1 With an extravagant CIA lunch ahead, keep things casual at breakfast with a stop at Bread Alone, where you can choose from still-hot pastries, organic oatmeal, or farm-fresh omelets.

2 Enjoy a leisurely drive to nearby Hyde Park (about 11 miles south via Route 9) to visit the 300-acre Springwood estate, the birthplace and lifelong home of the only four-term U.S. President, Franklin Delano Roosevelt. Both the president and his wife Eleanor are buried at Springwood, and the nearby FDR Presidential Library & Museum offers insight into his years in office.

3 Your taste buds are in for a treat as you enjoy lunch at the Culinary Institute of America's award-winning Ristorante Caterina de' Medici restaurant (make reservations). The menu celebrates authentic regional Italian cuisine in a dining room overlooking the gardens and the Hudson River. Expect such classics as beef carpaccio, gnocchi, and risotto, or head to the more casual Al Forno Trattoria for wood-oven pizza. Save room for dessert—the chocolate budino and affogato are Italian classics not to be missed.

4 After lunch, take a relaxed stroll around the exquisite formal gardens at the gilded-age Vanderbilt Mansion National Historic Site, as well as through its 1898 Gilded Age stone mansion.

5 Continue your amble into the past by spending the rest of the afternoon antique hunting in Rhinebeck at the Beekman Arms Antique Market, a multi-dealer emporium located in a large red barn.

6 Relax over pre-dinner drinks at the colonial-era taproom in the Tavern at The Beekman Arms, where you can soak in the ambience of America's oldest continually operating inn (dating from 1766).

7 If you can never have too much country paté or mussels in white wine sauce, continue the French theme with dinner at Le Petite Bistro, where CIA graduate Joseph Dalu's talent outshines the dated décor. If you crave something more contemporary, opt for Gigi Trattoria, where the innovative, farm-fresh Mediterranean cuisine ranges from zesty salads and flavorful flatbread pizzas to grilled fish and meats.


1 Admire the very same vistas that inspired writer Washington Irving and Hudson River School landscape painters on a morning stroll through Poet's Walk, a 120-acre riverfront parkland dotted with rustic footbridges and gazebos.

2 Refuel with a brunch at Calico, a cozy red-walled bistro where you can opt for the tempting frittata of the day or crab cakes with homemade tartar sauce. If you're looking for something a little livelier, head over to the The Rhinecliff, where a classic brunch menu is accompanied by live jazz (11:30 a.m. to 2:30 p.m.) and the dining room and patio have river views.

3 Finish your weekend with a bird's eye panorama of the Hudson Valley on a ride in a vintage 1929 biplane (select weekends, June through October) departing from the Old Rhinebeck Aerodrome. Or, if you prefer to keep your feet on solid ground, go shopping at the Woodbury Commons premium outlets nearby.

Where to Stay

For the best combo of budget-friendly rates and authentic eighteenth-century ambience, stay at the 73-room Beekman Arms and Delamater Inn (rooms from $155/night), which ranks as America's oldest continuously operating inn and offers both historic character and modern amenities.

If more contemporary décor is your thing, you can't do better than The Rhinecliff (rooms from $240/night), a renovated 1854 building that houses sunny rooms and suites, all with king-sized beds, cheery yellow décor, and stunning river views in Rhinecliff (where the Amtrak station is).

When to Go

Summer brings the Old Rhinebeck Aerodrome alive with weekend air shows featuring vintage Red Baron planes.

In the fall, the area's farms open their gates for apple and pumpkin picking, and Rhinebeck celebrates Halloween with a weekend parade and festivities.

Even winter can be enjoyable, especially because rates dip. December is again prime weekend season, as the area's Christmas tree farms lure families searching for the perfect evergreen. In addition, Rhinebeck celebrates an old Dutch tradition of Sinterklaas the first Saturday in December with a day of festive street parades and performances.

How to Get There

By car (from New York City): The drive takes a little less than two hours. To Millbrook Vineyard & Winery, take the Major Deegan (I-87) or the Henry Hudson Parkway North to the Saw Mill River Parkway North. Exit onto Taconic State Parkway North and travel to Route 44 Millbrook/Poughkeepsie. Turn right onto Route 44 East. Go 1 mile to Route 82 North. Turn left onto Route 82 and go 3 miles to Route 57. Turn right onto Route 57 and go 3.5 miles to Wing Road. Turn left onto Wing Road and turn right at the second drive to arrive at the winery. Afterward, return to Taconic State Parkway and head North to Route 199 (Pine Plains, Red Hook, Rhinebeck). Turn left onto Route 199 West and drive 3.8 miles before continuing onto Route 308 West. Drive 5.5 miles to Rhinebeck.

By train (from Penn Station in New York City): Amtrak runs frequent service to the Rhinecliff Station, and travel time is about ninety-five minutes. You'll need a car once you arrive; arrange in advance for Enterprise, in nearby Kingston, to pick you up.

Photo Credits