It is an area of 167 acres (68 ha) contains 272 buildings in a variety of architectural styles dating from over 200 years of the settlement's history.

[2] Its properties were developed primarily from the Colonial era to the end of the 19th century, when the district reached its present form.

Three U.S. presidents have passed through here, most significantly, Franklin D. Roosevelt, who chose the design for a new post office during the 1930s, and spoke at its dedication.

[1] European settlement in the Rhinebeck area dates to 1686, when a group of Dutch crossed the river from Kingston and bought 2,200 acres (890 ha) of land from the local Iroquois tribes.

[5] In 1703 the New York colonial assembly approved money for the construction of the King's Highway, later known as the Albany Post Road and today most of Route 9.

Three years later Traphagen bought a tract of land in Beekman's patent where the King's Highway intersected the Sepasco Indian Trail, the route today followed by Market Street.

[6] A decade later, in 1715, Beekman's son brought in 35 Palatine Germans who had fled religious persecution at home and had just concluded an attempt to produce naval stores for the British government on the lands of Robert Livingston to the north in what is now Columbia County.

[1] In the mid-1770s, a soldier named Richard Montgomery moved into the village with his new wife, a member of the Livingston family.

After being elected to the New York Provincial Congress, he was commissioned a general in the Continental Army, and died at the end of 1775 in the Battle of Quebec.

George Washington visited in 1796, dining at Bogardus's, the second Traphagen tavern, when he stayed at a nearby friend's house.

During the 1804 gubernatorial election, both Aaron Burr and Morgan Lewis used taverns in Rhinebeck as campaign headquarters.

Ten years later, Alexander Jackson Davis built the Henry Delamater House at 44 Montgomery Street.

Roughly 20% of the village's population during the Gay Nineties was in this business in some way, and the total crop was later estimated to have exceeded a million dollars in value some years.

[15] A third president, Franklin D. Roosevelt, himself a native of nearby Hyde Park, would play a role in the town's history during the later years of the Great Depression when he oversaw the design process for the new post office.

He had long promoted Dutch-style fieldstone as a material for public buildings in the area, and told the architects to use Henry Beekman's house (burned in a 1910 fire) as their model and some of its remaining stones for the post office.