Travel through three beautiful Dutchess towns: Rhinebeck and Red Hook, bordering the Hudson, are among the earliest settled portions of the country; Milan, inland, presents a sparsely settled rural contrast.

RHINEBECK covers 34.9 square miles of meadowland, small streams and wooded hills with lovely mountain vistas. Principal centers are the village of Rhinebeck and hamlet of Rhinecliff, where the Sepasco Indian Trail meets the Hudson. Formed as a town in 1788, it had been settled since ca. 1686. Illustrious descendants of the early Dutch and English patentees include the Beekman, Livingston, Astor, Montgomery and Schuyler families. It is said the Beekman tenants, Palatine refugees from Europe’s religious wars, named the town for their former home in Germany’s Rhine Valley. From the annals of town “family” history have come some of our nation’s greatest leaders and statesmen, including Revolutionary War hero General Richard Montgomery and Levi Parsons Morton, US vice president and governor of New York.

RED HOOK was part of Rhinebeck until 1812, and the 2 towns are geographically similar. In its 38.9 square miles there are 2 major centers: Red Hook Village inland and Tivoli on the river. Tradition holds that Henry Hudson’s crew named the area in 1609 for a hook-like land configuration near where they anchored. The surrounding hills were covered by red foliage, therefore the name “Red Hook.” It developed as an agricultural economy centered on the “River Places,” huge countryseats dating back chiefly to the early patentees. Farming, fruit growing in particular, is still a mainstay of town economy.

MILAN founded as a town in 1818 with 36 square miles, is inland of the river. It is one of the most rural and the least populated of all Dutchess towns, with no major center or even its own post office. Small hamlets grew up in the early 19th c. at Rock City and Lafayetteville. Although poor soils have discouraged large-scale agriculture, the terrain has great appeal. Some of the most beautiful roads and scenic views are found here.