Hudson Valley, New York

Amtrak from Penn Station reaches Rhinecliff (for Rhinebeck) or Hudson in 1.5-2 hours — the most scenic and most relaxed arrival approach. The Hudson Valley's river towns — Cold Spring, Beacon, Rhinebeck, Hudson, Catskill — each have distinct characters: Cold Spring has the finest Hudson River panorama from its main street; Beacon has the Dia:Beacon museum and a revitalized Main Street; Rhinebeck is the valley's most charming historic village with the Beekman Arms (the oldest continuously operating hotel in America, built in 1766); Hudson is the most sophisticated, with gallery-lined Warren Street and some of the best restaurants in the valley. A first afternoon walk along the Rhinebeck historic village, dinner at Terrapin restaurant for farm-to-table Hudson Valley cooking, and a walk to the river at sunset.

Blue Hill at Stone Barns in Pocantico Hills is the most influential restaurant in the American farm-to-table movement — Dan Barber's Rockefeller-estate restaurant and working farm has been setting the agenda for sustainable American cooking since 2004, and the multi-course tasting menu (based entirely on what the farm and its network of local suppliers are growing at the specific moment of your visit) is one of the most completely realized dining experiences in the United States. The Stone Barns Center for Food and Agriculture surrounding the restaurant is a 80-acre working farm with heritage breed livestock, seasonal vegetable gardens, and educational programs. Reservations at Blue Hill are extremely difficult — book 60+ days ahead. Alternatively, the Stone Barns Blue Hill at Stone Barns cafe is excellent for lunch without the reservation difficulty.

Dia:Beacon in Beacon, NY (Amtrak or 90-minute drive from NYC) is the finest collection of large-scale post-war American art in existence, displayed in a converted 1929 Nabisco box-printing factory with 240,000 square feet of daylit gallery space. The permanent collection includes Richard Serra's monumental steel sculptures, Dan Flavin's neon light environments, Donald Judd's aluminum boxes, and Robert Irwin's light installation — all presented at a scale and with the physical space to be genuinely overwhelming in a way that other museums cannot replicate. The Beacon Main Street, revitalized by the museum's arrival in 2003, has become one of the Hudson Valley's most interesting restaurant and gallery strips. Lunch at the Beacon Museum cafe or Dogwood restaurant on Main Street.

The Hudson Valley has the finest concentration of Gilded Age architecture in America. Hyde Park contains three National Historic Sites within 10 miles of each other: the Vanderbilt Mansion (a 54-room Italian Renaissance château designed by McKim, Mead & White for Frederick Vanderbilt), the Franklin D. Roosevelt Historic Site (Springwood, the family home where FDR was born and buried), and the Eleanor Roosevelt National Historic Site (Val-Kill, her private retreat that is the only NHS dedicated to a First Lady). Olana State Historic Site south of Hudson is the extraordinary Persian-Islamic castle home of landscape painter Frederic Edwin Church — the most famous Hudson River School painter designed his house, landscape, and the entire 250-acre view as a single composition. The view from Olana's hilltop toward the Catskills over the Hudson bend is one of the landscapes Church spent his life painting.

The Catskill Mountains west of the Hudson — the range whose misty forests, waterfalls, and specific quality of light inspired the first American art movement — are accessed via the Kingston-Rhinecliff Bridge. Woodstock, 15 minutes into the mountains from Kingston, is the most famous small town in American cultural history: the 1969 festival was actually at Bethel, 60 miles away, but Woodstock's own music and arts scene had been legendary since the early 20th century. The Overlook Mountain trail from Woodstock (4.6 miles round trip) climbs to a 3,140-foot summit with extraordinary views over the Hudson Valley. Catskill Center for Conservation has excellent resources on the mountain ecology. Saugerties village on the Hudson, with its 1825 lighthouse accessible by a 0.5-mile trail at low tide, is one of the valley's most charming stops.

The Hudson Valley is one of America's great agricultural regions — apples, pears, peaches, corn, and a tremendous variety of heirloom vegetables in the farms between the River Road and the Catskill foothills. Pick-your-own orchards (Greig Farm in Red Hook, Migliorelli Farm in Tivoli) provide the most direct connection to the landscape in autumn (September-November). Hudson, 30 miles north of Rhinebeck, is the valley's most sophisticated small city — its Warren Street is lined with antique shops, art galleries, and restaurants of the highest quality. Hudson Distillers and the Tuthilltown Spirits distillery at Gardiner (the first whiskey distillery to open in New York State after Prohibition, makers of Hudson Baby Bourbon) are excellent stops for craft spirits. Dinner at Fish & Game in Hudson — the Hudson Valley's most celebrated restaurant, a converted 1880s blacksmith shop.

Amtrak back to Penn Station from Rhinecliff or Hudson (1.5-2 hours) is the most comfortable departure, or a car service to JFK or EWR for international connections. A final morning walk along the Hudson River itself — the Walkway Over the Hudson at Poughkeepsie (the longest elevated pedestrian bridge in the world, converted from an 1889 railroad bridge, 212 feet above the river) provides the most extraordinary river view in the valley, with the Catskills visible to the west and the Hudson Highlands to the south. Take home local apple cider, Migliorelli Farm honey, Tuthilltown Hudson Baby Bourbon, and a print from one of the Hudson River School artists available at the Olana museum shop. The Hudson Valley's specific quality of autumn light has been influencing American culture since the 1820s — and after a week here, you'll understand why.