This area includes the riverfront sections of the towns of Clermont, Red Hook, Rhinebeck and part of Hyde Park.

From the colonial era to the early 20th century, the district was characterized by large "country seats" built by members of the Livingston family, such as Clermont Manor and Montgomery Place, both National Historic Landmarks.

The slope allows for expansive views from cleared areas of not only the river and the higher glacial ridges on the west side but the Catskill Mountains in the distance.

This prospect has attracted homebuilders from the earliest times of settlement to the present, and is considered an essential quality of the district: "There is a sense of openness that belies [the district']s constrained width because it is counterpointed by the persistent vision of the mountains in the west," writes architectural historian Neil Larson in the NHL application.

"The district benefits from such a direct and imposing profile of the mountains, and its legendary country estates would lose much of their appeal without this extraordinary setting.

"[4] The district's permanent human population and attendant development is densely concentrated in the small riverside communities — from south to north, Rhinecliff, Barrytown, Annandale and Tivoli.

This, too, reflects the years of estate and country house development, as well as the historic importance of the river and rail transportation corridor to the local economy.

[4] The history recognized by the NHLD designation began in 1688 with the first colonial land grants and continues to the end of country house development in the area around 1940.

This, as well as Clermont's name and position, strategically overlooking the Hudson and its commercial traffic, was influenced strongly by European feudal practices, setting a pattern other estates in Livingston Manor were to follow long after his lifetime.

[4] His son Judge Livingston followed feudal tradition further by marrying Margaret Beekman, daughter of Henry, another large local landowner whose holdings were concentrated around present-day Rhinecliff, which grew up around them.

They were joined by her son-in-law, Governor Morgan Lewis, who settled on 334 acres (1.35 km2) south of Rhinecliff in 1790 and built a small house there.

The Romanticism that flourished in the succeeding years drew a good deal of its inspiration from the Hudson Valley, in the form of the Hudson River School in painting and the architectural theories of Andrew Jackson Downing, put into practice there and elsewhere by his protegés Calvert Vaux and Frederick Clarke Withers as well as Richard Upjohn and Alexander Jackson Davis.

"No part of the United States had a more correct kind of Romantic scenery to offer", wrote Catskill historian Alf Evers.

The Livingstons, as was customary for the owners of large country estates at the time, opened their grounds to the public on weekends as parks, and to this end followed Downing's theories of landscaping by building curving paths and rustic benches and shelters from which to admire the river and distant mountains.

Occasionally these led to "Anti-rent Wars", uprisings that sometimes directly affected the landlords, as in 1832 when Lewis's mansion was burned, supposedly by angry tenants.

The Livingstons' hold on the area diminished through the continuing divisions of their property and the abolition of three-life leases under a new state constitution in 1840.

Many of their homes were set among the winding rural roads that had served to divide the farmed portions of property, closer to the river, from the estates and surrounding gardens.

They built picturesque stone walls and elaborate gateways that enhanced the rural character of the landscape but also served to emphasize the exclusivity of ownership.

The new money of the Gilded Age had come from industrialization, not landownership, and preferred newer hot spots like Long Island and Newport for its summer mansions and retreats, or followed Jay Gould and the Rockefellers in building or improving estates further downriver, closer to the city.

[4] The influence of the newer wealth and its tastes on design and living was still felt along the Hudson most in the changed approach to the pleasure grounds around the estates.

The last major country seat came when Harrie T. Lindeberg built Fox Hollow on the thousand acres (4 km2) Tracy Dows had acquired.

[4] In 1860, the Bard family had provided money so that a small Episcopal seminary near their Tivoli estate could be expanded into St. Stephen's College, later renamed after them.

Others, like Clermont, the Mills Mansion and Wilderstein, were eventually given to the public or private trusts and turned into museums of the life once led in them.

The desirability of open space overlooking the river is a source of constant development pressure on the district, as builders look to serve buyers priced out of growing suburbs further south in the valley, yet still looking for a rail commute to the city via Amtrak or Metro-North (via Poughkeepsie).

[9] Clermont, Red Hook and Tivoli have so far not chosen to apply any additional standards and continue to preserve the district through their existing zoning and applicable New York state laws requiring historical and environmental reviews in certain areas.

Egbert Benson, a congressman, federal judge and New York's first attorney general, built his law practice in what would later be Tivoli.

As a child, his wife Eleanor lived at Oak Lawn, the Tivoli estate of her grandmother Mary Ludlow Hall, for several years after the death of her mother.

Henry James, a frequent visitor to his uncle's home at Linwood, makes several references to Rhinebeck and other locales within the district in his writings.

Two of them, Walter Becker and Donald Fagen, cofounded the rock group Steely Dan, and wrote two songs about Bard and places near it: "My Old School", from Countdown to Ecstasy; and "Barrytown", on Pretzel Logic.

In 2003, the Frank Gehry-designed Richard B. Fisher Center for the Performing Arts brought innovative contemporary architecture back to the district.