Driving Tours

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 1609 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.

Takes you through another part of the Town of Washington, this time leading eastward through the center of the Village of Millbrook, the hub of local government. Fertile soils in this area provide an agricultural home to both Cornell Cooperative Extension/Farm and Home Center and the Institute of Ecosystem Studies. The Town of Amenia, named by Dr. Thomas Young, a poet, is from the Latin “Amoena,” meaning pleasant place. It is the site of the annual World Peace Festival and home to Troutbeck, the former Spingarn Estate that hosted the first meeting of the NAACP.

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.

Takes you on a journey through the Towns of Union Vale, Beekman, Pawling and Dover. The tour begins in Union Vale, best noted for its Clove, a beautiful, narrow valley, then winds through Beekman, with its charming, old farm houses. The Town of Pawling, dating back to 1788, was home to newsmen Edward R. Murrow and Lowell Thomas, and the Rev. Norman Vincent Peale. Dover, encompassing the hamlets of Dover Plains and Wingdale, was a stopover for New England cattle "drovers" on the way through the Harlem Valley.

Explores the Towns of Wappinger, Fishkill, East Fishkill and the City of Beacon. The tour begins in the hamlet of New Hackensack, which was settled by Dutch farmers from New Jersey around 1750. It winds through the Village of Wappingers Falls, then south to Stony Kill and Mount Gulian, to Beacon, with vistas of the Fishkill Range and Mount Beacon. The tour encompasses the numerous historic sites clustered around the area of Fishkill and provides a view into the historic past of southern Dutchess County.

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