Start in Kinderhook on Rte 9. Visit Lindenwald, the Martin Van Buren National Historic Site. Van Buren, the eighth President of the United States, purchased the estate in 1839 and lived here the last 21 years of his life. In Hudson take Rte 9G south to Olana State Historic Site, the home of Hudson River School painter Frederic Church. Tour the home and gardens of this 250-acre estate.
Take Rte 9 south to Livingston and visit Fix Brothers Fruit Farm on White Birch Rd, just off Rte 9G. Pick your own apples, pumpkins and gourds.
Continue south on Rte 9 to Rhinebeck and the Old Rhinebeck Aerodrome Museum, a living history museum of antique aviation featuring one of the largest collections of early airplanes. The Aerodrome also has automobiles, motorcycles, early engines, weekend air shows and memorabilia from 1900-1935.
Have dinner and overnight in Rhinebeck at the Beekman Arms & Delamater Inn, America's oldest operating inn. Nearby, Red Hook is home to many eclectic restaurants.
Head south on Rte 9 to Hyde Park and visit the Vanderbilt Mansion, the grand estate of Frederick Vanderbilt. Walk the grounds, hike carriage trails, or picnic at the magnificent Hudson River overlook.
Visit the Culinary Institute of America; take a tour and eat lunch. This world-renowned cooking school offers classes and boot camp for serious foodies and its student-run, top-rated restaurants feature the culinary stars of tomorrow. Book ahead!
Take Rte 9 south to Beacon and check out Dia:Beacon, featuring art from the 1960s to the present. Artists' work on view include Joseph Beuys, Donald Judd, On Kawara, Agnes Martin, Richard Serra and Andy Warhol. Continue down Rte 9 to the town of Garrison and take in the beautiful mansion and gardens at Boscobel Restoration. Overlooking the Hudson River and West Point, this museum is a restored early 19th-century Federal-style mansion and contains the nation's leading collection of furniture and decorative arts.APPROXIMATE MILEAGE: 85 miles