It is the original site of the mid-17th century Dutch settlement of Wiltwyck, which was later renamed Kingston when it passed to English control.

Five years later, as the historic value of the entire uptown area became apparent, the larger Stockade District was created, subsuming the original one.

The formal recognition of its historic importance has led to contentious battles in local government over proposals to redevelop the area.

The block of Wall to the south is dominated by the old county courthouse and the Old Dutch Church, whose cemetery and yard is apart from the Senate House State Park, the only significant green space in the district.

[1] Six years later, by 1658, Dutch colonial governor Peter Stuyvesant ordered all settlers to move to the village, behind the stockade whose construction he personally supervised.

George Clinton was chosen the first governor, and John Jay, later the first Chief Justice of the United States, opened the first term of the New York Supreme Court in Kingston.

A total of 326 buildings inside and outside of the stockade were destroyed, with only a handful, such as the Tobias Van Steenburgh House, remaining untouched.

New commercial buildings were erected in the styles such as Federal architecture Greek Revival popular in the century's early decades.

[2] A few years later, in 1908, George Clinton, long buried in Washington, was brought back to Kingston and reburied in the yard of the Old Dutch Church with full honors.

[8] In the early 21st century, the county sponsored an archaeological dig at the site of the Persen House, one of the four at the Crown-John intersection, as part of efforts to restore it and make it a museum.

[24] At the time the condominium project was failing, in 2008, CVS Pharmacy proposed a 12,900-square-foot (1,200 m2) store on Washington Avenue and Schwenk Drive.

[26] One city alderman tried to stop the project with a building moratorium along Washington,[27] which received the support of the Stockade's business association.

[29] The city's Planning Board eventually approved the project,[30] and construction crews began clearing the site in September 2009.

[31] The city and preservationists were able to work together on one project, the restoration of the 1899 Kirkland Hotel at Clinton Avenue and Main Street in the southeast corner of the district.

[33] In 2003 the Rural Ulster Preservation Company (RUPCO), a local nonprofit organization devoted to housing, bought the hotel with the intention of completing the restoration.

In 2008 Rep. Maurice Hinchey helped the city secure $1.3 million in federal grants to rehabilitate uptown and the Stockade District.

[7][8] The following spring the city announced it would use some of the money to reverse the direction of traffic on several of the one-way streets within the district to ease travel through and around it.

[38] Later that year City council debated whether to restore the traffic light at North Front and Wall or keep the stop signs.

[39] Just prior to completion of the canopy project, graffiti artists painted red goats on eleven of the new sidewalk planters, raising a furor.

[42]The city's Landmarks Preservation Commission reviews applications for new construction, including significant alterations to existing structures, in the Stockade District.

[43] It may consider, and request modification of, many elements of the proposed construction, including roof shape, walls and paving, in the interest of protecting the Stockade's historic character.

Its 400 members have actively opposed some recent projects that they believed would adversely affect the district, to the point that some critics have referred to the group as Friends of Hysteric Kingston or Enemies of Development.