The estate is situated atop Watch Hill's namesake hillock, which was used as a lookout point during the Seven Years' War and the American Revolution.

[1] Watch Hill, on which the house would later be constructed, was the site of a signal station during the French and Indian War, and used by Colonial forces as a lookout spot for British ships during the American Revolution.

In order to stabilize the badly eroded hillside, George Grant Snowden Jr. had thousands of granite boulders put in place,[5] which remain there to this day.

Ownership of the property passed to George and Pearl's son Robert Burns Snowden, who died in an automobile accident when driving from the house in 1941, at age 23.

[7] Rebekah apparently was quite unpopular with her neighbors, doing unusual things such as cleaning her pool with champagne,[16] and gambling with a wide range of guests, such as Spanish artist Salvador Dalí.

[2] From 2013 to 2016, she received widespread press coverage for hosting annual American Independence Day parties on the estate, featuring numerous celebrity guests and lavish decorations often depicted on Instagram.

[30] Vanity Fair opined, "few annual celebrity-hosted gatherings are surrounded by as much outsized mythos as Taylor Swift's Fourth of July party".

[32][33] The parties were not held from 2017 to 2022; although Swift did not disclose why, media outlets named her step-away from the spotlight and the presidency of Donald Trump as reasons.

[37][38] In 2014, she faced criticism from local residents over a proposal to rebuild a seawall on her property which would reportedly impede public access to the beach.

Swift responded that she sought to repair damage from coastal erosion, and the area of seawall was on her private beach, which had been used by the public for years before her purchase.

[39] Following a lawsuit in April 2017, the Rhode Island Supreme Court upheld a lower-court decision that landowners in Westerly can put up fences to keep strangers off their beach.

[40] The attorney general's office and environmental groups argued that the land had been dedicated to the public more than a century ago, but the court disagreed, ruling that the beach is privately owned.

[42] The tax was widely viewed as an obstacle for future tourism in the state, especially since people with second homes spent money without straining infrastructural resources such as school systems.

[2] Swift held the "Secret Sessions" at High Watch in 2014 and 2017, hosting listening parties for select Swifties prior to the release of her albums 1989 and Reputation.

[43] On April 2, 2019, a stolen car crashed into the estate's gates following a police chase that started in a neighboring town in Connecticut.

[45] Swift's 2020 studio album Folklore features "The Last Great American Dynasty", a song about the house and life of Rebekah Harkness.

[52][53] The lyrics detail parallels between Harkness's and Swift's unfavorable press reception at various points due to their personal lives and residence.