Explores the Towns of Rhinebeck, Red Hook, and Milan. Rhinebeck boasts of 35 miles of meadowland, small streams, and wooded hills with lovely mountain vistas. Tradition holds that Red Hook was named by Henry Hudson's crew in 1509 for a hook-like configuration of land near where they anchored, covered by red foliage at that time of year. Milan, a rural and sparsely populated town, offers some of the most beautiful roads and scenic views found here.

Winds through the Towns of Pine Plains, Northeast, Amenia, Washington and Stanford. Pine Plains is the site of what may have been the country’s first Christian congregation of Native Americans, ca. 1742. The Town of Northeast, dating back to 1788, is where the quaint Village of Millerton is found. With farming its oldest industry, Stanford attracts visitors to its markets, ranches and wineries. The Town of Washington, named for General George Washington, hosted Revolutionary troops and Quaker meetings and schools.

Leads the traveler through the Towns of Hyde Park, Clinton and Pleasant Valley. In Hyde Park, Franklin D. Roosevelt made his lifelong home. Clinton, named for New York's first governor, was settled in the early 1700s by New England Quakers. Mill sites along the little Wappinger Creek and the crossroad enterprises became the core of early hamlets. And in Pleasant Valley, a plank turnpike between Connecticut and Poughkeepsie provided farmers a route to Hudson river markets. The Wappinger Creek wanders among the town's low hills.

Encompasses the City and Town of Poughkeepsie and the Town of LaGrange. The tour begins north of the city and winds into the town past the remaining farms and orchards of LaGrange. The City of Poughkeepsie courthouse, center of state government during the Revolutionary War, was the site of New York's ratification of the U.S. Constitution in 1788. The Town of Poughkeepsie is best known today as the home of IBM and Vassar College. Called "Freedom" when formed as a town in 1821, LaGrange was renamed in 1829 by enthusiastic patriots in honor of the Marquis de Lafayette's farm in France.