One of the best escapes 100 miles from midtown Manhattan is the village of Rhinebeck, New York — a "haute hippie" sort of place situated near the Hudson River. The town features an eclectic mix of architecture, sustainable dining, and residents (and weekenders) from all walks of life. It's a great place year-round, but summer features some of the best farmers' markets, antiques shows, and country fairs you'll find anywhere.
HOW TO GET THERE
Amtrak runs from Penn Station to Rhinecliff-Kingston in Rhinebeck, and you can call for cabs to get around. But the best move is getting your hands on a steering wheel and driving the scenic Taconic Parkway.
WHERE TO STAY
You're not going to find a lot of five-star establishments in Rhinebeck, and that's what keeps the area feeling small and special. Get a room at the centrally located Beekman Arms (the oldest inn in America, by the way) where you'll be in striking distance of morning coffee and croissants from Bread Alone, newspapers galore, cute shops full of antiques, and Stickles, a good ol' five-and-dime store that kids adore. If you're looking for a more boutique feel, head north to Tivoli, where the Madalin Hotel has eleven newly renovated rooms by the designers of NYC's Chelsea Hotel. Old-school touches (nice innkeeper, no key cards) mix with new-school style (flat screens, WiFi), not to mention Madalin's Table, a tavern and dining room with awesome grass-fed beef burgers, seared cod, grilled vegetable pizzas, and kid's pastas du jour. There's also a wide porch where you can savor a little Sauvignon blanc and watch the world pass — very slowly — by.
WHERE TO EAT
Food (in every form) is the biggest game in town. Balance a high-end dinner at Le Petit Bistro with killer ice cream cones from Del's Dairy Creme (7775 Albany Post Road) where $2 still buys an enormous swirl of soft-serve goodness. Everything in town is kid-friendly, but the highlight for all ages is Gigi's Trattoria, where a bustling outdoor patio, homemade butternut squash gnocchi, and "skizzas" (thin-crust pizzas in unique combinations such as porchetta with fennel salami, red onion, tomato, and mozzarella) make for a mellow evening.
More Italian goodness happens at Mercato Osteria & Enoteca in nearby Red Hook. There's a vaguely Tuscan ambiance and a blackboard of the day's farm fresh specials. Meals are lovingly prepared by seventh-generation pasta man Francesco Buitoni, who incorporates wild leeks and sweet sausage from nearby Northwind Farms with spectacularly fresh fish and risottos (wild mushroom, smoked salmon, asparagus). Save room for the flourless chocolate cake.
Other great foodie bets in the vicinity: The Local, chef Wes Dier's latest "eclectic New American" addition to the community (high marks for the phyllo-wrapped Coach Farm goat cheese with Sky Farm lettuces, fig jam, onions, and crostini); Osaka, for steaming steak terikayi dinners that will delight kids; and Garden Street Cafe at Rhinebeck Health Foods (24 Garden Street), for a picnic of "Avocado Supreme" sandwiches and a serious vegan vibe.
WHAT TO DO
Spend a Saturday or Sunday checking out the bi-planes at the Old Rhinebeck Aerodrome (June through October 16th). Peep automobiles and motorcycles from the golden "barnstorming" era of aviation, and watch an air show of sky-high twists and turns — complete with flying aces and billowing neck scarves. After watching planes swoop, you'll want to head to Wilderstein, an immense Queen Anne style country house-turned-museum surrounded by walking trails. If possible, plan your trip around the Dutchess County Fair, an extravaganza of fried dough and rides that happens in late August. Little kids can go nuts with bumper cars and livestock competitions, strolling performers and live bands.
WHERE TO SHOP
There are a lot of stylish ex-city folk around, and Rhinebeck doesn't disappoint in the retail arena. No Sugar has sweet separates for little kiddies from brands like 3 Pommes and 7AM, as well as unique pieces for grown-ups. For a carefully edited selection of things for the home visit Hammertown (conveniently located next door to Gigi's Trattoria). Peruse reading material and music at Oblong Books, a classic book shop hub with meaningful staff picks and readings by local authors. Paper Trail stocks cards and gifts by small letterpress printers from across the country. There will be no shortage of souvenirs.