1. Where to Stay
Book a weekend stay three months in advance at the nine-room Rhinecliff Hotel (from $180), a former live-music venue turned Victorian hotel. All rooms include private balconies with views of the Hudson River, and the hotel is an easy walk to the waterfront.
Sip some complimentary sherry from the decanter in your room at Beekman Arms (from $125), the oldest continuously operated hotel in the U.S., founded in 1766. The no-frills country-style spot is steeped in past presidential history: George Washington lodged in room 21 during the Revolutionary War, and the Clintons hosted Chelsea’s rehearsal dinner here in July.
Lounge in a white-tiled Jacuzzi in the Ivy Room at Veranda House (from $180), a floral-themed B&B outfitted with lace curtains and nineteenth-century antiques. Owner Yvonne Sarn creates breakfast specialties like ratatouille and goat-cheese crêpes and blueberry custard casserole.
2. Where to Eat
Listen to the Will Smith Trio play live during the Rhinecliff’s Sunday jazz brunch (11:30 a.m.-2:30 p.m.). The Hudson Valley–focused menu here relies on ingredients sourced from local farms, from the eggs and housemade porchetta to the trotters. Arrive before noon to snag a table on the canopy-covered patio with views of the river.
Sample gussied-up French classics like frogs’ legs, escargot, and Coquille St. Jacques (sautéed scallops) at Le Petit Bistro, a cozy spot decked with white tablecloths and low-lit wooden lanterns. Chef Joseph Dalu shops at the Rhinebeck Farmers Market each week to create the daily-changing chalkboard menu. Make a reservation a week in advance.
Gorge on the Hibachi for two ($48)—a platter heaped with chicken, shrimp, filet mignon, and lobster (alongside soup, salad, and noodles) at Momiji (43 East Market Street; 845-876-5555), a six-month-old sushi and steak house with a cross-hatched bamboo divider and a bar with an iridescent green glass backsplash. Reserve one of the four Teppan-Hibachi tables to watch the chef prepare your meal in front of you.
3. What to Do
Rent a mountain bike from Rhinebeck Bicycle Shop (10 Garden Street; 845-876-4025; $25/day) and ride eight miles north the heavily wooded River Road, which traverses the back end of some of the area’s large riverfront estates. Follow the trail onto the leafy campus of Bard College and pause to check out the Fisher Center for the Performing Arts, a sculptural building of undulating silver canopies designed by Frank Gehry.
Pedal two miles south of Fisher Center to the Montgomery Place Orchards Farm Stand (Routes 199 and 9G; 845-758-6338), a market showcasing seasonal produce, cheese, grass-fed beef, and lamb from local farmers. Stock up on Doug and Talea Fincke’s renowned fruit jams and mason jars full of Annandale Atomic hard cider.
Take the East Tower route in Ferncliff Forest (845-876-3196), a preserve two miles outside Rhinebeck Village with eleven marked trails. Ride until you reach the scenic observation tower, which offers aerial views of the Hudson Valley and the surrounding Catskills.
Kayak through the tall reeds and purple loosestrife of Tivoli Bays, an estuary populated by snapping turtles, osprey, and muskrats (Hudson Valley Kayak Tours; 845-518-1455). Book the sunset tour (5 to 7 p.m.) to admire the riverscape at dusk.
4. Insider’s Tip
The Town of Rhinebeck is home to the Omega Institute, a 195-acre educational retreat, holistic wellness center, and spa eight miles south of Rhinebeck Village. Though most guests drive or reserve taxis to the sprawling campus—a $56 ride round-trip—there’s a lesser-known shuttle that departs from the Amtrak station in Rhinecliff and Beekman Arms in Rhinebeck on Fridays and Sundays for $20 round-trip (on the hour, 1 to 7 p.m.). Book a week in advance to secure a seat.
5. Oddball Day
After a day outdoors, check out some of Rhinebeck’s cultural diversions. Start with a bowl of the specialty citrus oatmeal—rolled oats, flaxseed, and dried fruit simmered in fresh-squeezed orange juice—at Bread Alone Bakery, also known for its artisinal breads. Then head over to Wing & Clover, a storefront, gallery, and workshop space that features the work of Hudson Valley artists. The spot offers two- to three-hour workshops ranging from oil painting to paper-cutting (reserve a month in advance). Then kick back at the four-month-old Grand Cru Beer & Cheese Market, a storefront café that sells a rotating selection of New York State craft beers, like farmstead-brewed Ommegang from Cooperstown. Next, swing by Upstate Films, an intimate theater that attracts ardent film buffs, showing first runs of foreign and art-house films on two screens ($7.50). This month’s selection includes Winter’s Bone, winner of the 2010 Sundance Film Festival’s Grand Jury prize. Then pull up a stool at the wraparound copper-topped bar of Terrapin for dinner, a church turned boisterous bistro specializing in comfort food like Asian barbecued pork po’-boys and burgers. Cap off your night to the tunes of Miles Davis and Chet Baker at the month-old Zen Dog Café, a multi-room bar, bookstore, and jazz-themed art gallery serving specialty cocktails and wine tasting flights.
Research affordable area lodging at the Rhinebeck Chamber of Commerce.
About Town offers a community guide to Northern Dutchess County, including events and seasonal area attractions.
Read up on regional farms and restaurants at Valley Table.
Check out vendors and special events at the Sunday Rhinebeck Farmers Market.