Less than a two-hour train ride north of Manhattan, Rhinebeck is a quirky slice of New York history with all the trappings of a quaint upstate town. Home to the state’s Sheep and Wool Festival and the big annual Dutchess County Fair, this village in the foothills of the Berkshire Mountains packs a pleasant punch, between the natural beauty of the Hudson Valley, non-commercial shopping avenues, time-honored traditions, and “hiya neighbor” local spirit; don’t be too surprised when a stranger invites you to an open house for dinner—and you find yourself wanting to extend the weekend just one more day.

What to do
American history buffs, commence drooling. Rhinebeck is located in the center of the National Historic Landmark District, a stretch of 16 miles of contiguous riverfront estates associated with the Hudson Valley’s rich and famous of the 18th, 19th, and early 20th centuries. Among the most legendary of the estates include those of the Vanderbilts, former President Franklin D. Roosevelt (Hyde Park), and Samuel Morse.

Rhinebeck is also an ideal destination for restless New Yorkers seeking some open-air adventure. The town and its surrounding area cater to almost any outdoor sport you can imagine; biking, hiking, horseback riding, and camping, just to name a few. Under the intensifying spring sun, the cool rippling waters of the Hudson may prove too tempting. At their Norrie Point Paddlesport Center in Staatsburg, a town between Hyde Park and Rhinebeck, Atlantic Kayak Tours (845.889.8461, atlantickayaktours.com) offers beginners kayaking tours on the Hudson for $50/person, including equipment.

However, if you chose to stay in town, there is still plenty to do and explore. Rhinebeck is renowned for its antique markets. Two to try are Asher House Antiques (6380 Mill Street, Rhinebeck, 845.876.1794, asherhouse.com) for antiques and home furnishings, and The Antique Market, an antique emporium housed in a red barn behind The Beekman Arms Inn (Route 9, Rhinebeck, 845.876.3477, beekmandelamaterinn.com).

Upstate Films (Route 9, Rhinebeck, 845.876.2515, upstatefilms.org) is Rhinebeck’s resident movie theater. In contrast to the town’s sleepy charm, Upstate shows an eclectic mix of what’s current in international and independent cinema.

Timeless To-Dos

One of Rhinebeck’s great attractions is the Old Rhinebeck Aerodrome (Stone Church Road, Rhinebeck; 845-752-3200; oldrhinebeck.org), a “living museum” of antique aviation. The Aerodrome’s hangar houses one of the largest collections of “aeroplanes” in the world, several of which take flight during weekend air shows.

And if watching a reenactment of a World War I dogfight rouses your inner Red Baron, the Aerodrome offers rides in an authentic 1929 New Standard open-cockpit biplane for up to four passengers for $65/person. Flights are booked on a first come/first serve basis every Saturday and Sunday June through October (reservations are not accepted). Pre-arranged weekday rides are also available.

Another one of Rhinebeck’s great summer attractions is the Hyde Park Drive-In (located opposite the FDR estate at 510 Albany Post Road, Hyde Park; 845-229-4738; hydeparkdrivein.com), located about 15 minutes from Rhinebeck. This family-owned drive-in has one screen and of course, a concession stand for indulging your guilty movie snack pleasure. During the summer months, a Farmers Market operates out of the drive-in from 10am to 2pm. A fun fact, New York remains one of the Top 5 Drive-In states, with nearly 30 Drive-Ins in operation currently and seasonally.

Where to eat
For breakfast, take a stroll through the town to find a cozy café that’s just the right fit. New York City visitors will recognize Bread Alone, the organic Hudson Valley bakery of Greenmarket fame (45 East Market Street, Rhinebeck, 845.876.3108, breadalone.com).

The Rhinebeck Deli (112 East Market Street, Rhinebeck, 845.876.3614) is a must-stop for packing your lunch to go. A much nicer feel than your typical New York City deli, mingle with locals while you pick-and-chose from a selection of Boar’s Head cold cuts to customize your sandwich.

The Rhinebeck Farmers Market (Municipal Parking Lot, East Market St.)—voted best farmers market in the Hudson Valley by Hudson Valley Magazine for the last two years—reopens for the 2010 season on Mother’s Day, Sunday, May 9. If you’re visiting that weekend, make sure to stop by for some fresh produce or homemade tarts, and free seedlings for you or your mom.

Starr Place restaurant and bar is a convenient spot for lunch or dinner if you plan on catching a movie next door at Upstate Films (6417 Montgomery Street, Rhinebeck, 845.876.6816, starrplace.com). This sophisticated eatery serves up American and Mediterranean style cuisine and live music every Saturday night. On warmer nights, grab an outdoor table and observe the quiet bustle of foot traffic as you dine.

Where to stay
Rhinebeck is home to The Beekman Arms, America’s oldest operating inn (Route 9, Rhinebeck, 845.876.7077, beekmandelamaterinn.com). Located in the center of Rhinebeck, the historic hotel is within walking distance of the town’s attractions. The inn has remained true to its colonial heritage, retaining many of its original structural features since its founding in 1766. Along with the basic amenities, each of The Arms’ 23 guest rooms comes standard with a decanter of sherry. The Tavern at The Beekman Arms is open daily for lunch and dinner, and non-guests are also invited to enjoy a meal here.

For a true taste of the wild countryside, consider staying at the Whistlewood Farm Bed & Breakfast, situated near the Rhinebeck Performing Arts Center, Rhinebeck Tennis Club, and Old Rhinebeck Aerodrome. Wake up to the sound of whinnying horses or the smell of a homemade breakfast. Double occupancy rates start at $165. (52 Pells Road, Rhinebeck, 845.876.6838, whistlewood.com)

If you are looking for a more intimate lodging experience, Rhinebeck has many cozy bed and breakfasts to suit your fancy. For a complete list of Rhinebeck lodging, visit the Rhinebeck Chamber of Commerce online at rhinebeckchamber.com/lodging.

How to get there: Rhinebeck is easily accessible from New York City by trains out of New York Penn Station or Grand Central Station. From Penn Station, Amtrak will take you to Rhinecliff, a small town outside of Rhinebeck. MetroNorth will take you to Poughkeepsie, and Rhinebeck is less than a 20-minute cab ride from there.