The land is themed after idyllic (often reductionist) retrospectives on American colonialism and nationalism, particularly in the era of the American Revolutionary War. The approximate years of theming being 1670s/1680s-1870s.
- The Admiral Joe Fowler Riverboat:
- The Mike Fink Keel Boats:
- Ye Olde Christmas Shoppe:
- Memento Mori:
- Liberty Square Portrait Gallery:
- The Yankee Trader:
- Olde World Antiques:
- The Heritage House:
- Mlle. Lafayette's Perfumerie:
- The Fife and Drum Refreshments:
- The buildings are arranged in an architectural progression starting from the entrance from the centre of Magic Kingdom park being themed around the late-17th century while progressively changing to the 18th and 19th centuries. With many of the buildings, this is marked by years on the addresses which coincide with the years the buildings represent.
- There are a number of design choices made throughout the park to try and emulate the colonial setting:
- Instead of having hinges, windows will often be latched on by leather belts as metal was being saved during the revolutionary war.
- With the exception of restaurant washrooms, there are no rest-room areas in the land as indoor plumbing had not been invented.
- In the centre of the path throughout Liberty Square there is a brown path supposedly made to reflect the exposed canals of human-waste that settlers would throw their excrement and waste into.
- Multiple allusions to Washington Irving's ghost story, the Legend of Sleepy Hollow can be found in Liberty Square.
- An advertisement for Music & Voice Lessons can be seen by the Ye Olde Christmas Shoppe, being held by the story's protagonist Ichabod Crane.
- The Sleepy Hollow Inn obviously takes its name from the story. In addition to this, the logo for the shop has the Headless Horseman on it. The store is dated to 1790 which is the year that the Legend of Sleepy Hollow is set in. The building is also inspired by the real-life, "Sunnyside" which was the basis for Wolfhert's Roost where Irving stayed in Tarrytown.
- Outside of the Sleepy Hollow Inn there used to be parcels addressed to Ichabod Crane and Abraham "Brom Bones" van Brunt, both of whom are characters from the book. The crates also state that Brom lives in, "Ma Irving's Boarding House" as an allusion to the story's author Washington Irving.
- A window near Sleepy Hollow Inn has the halloween party-list possessed by Katrina Van Tassel in the film. The list mentions Hans van Ripper, Brom Bones, Ichabod Crane, and Dofue Martling who are all book characters. Near the list is an open locket, curiously containing a photo of both Katrina and Ichabod as they appeared in their animated Disney incarnations. The list is also strangely resting on an open text of Washington Irving's book the Legend of Sleepy Hollow.
- While not a reference to the Legend of Sleepy Hollow, the Haunted Mansion's pet-cemetery features a tombstone and statue dedicated to the late Mr. Toad. This is notable here as Toad's Disney appearance was alongside the Disney retelling of the Legend of Sleepy Hollow in the 1949 film, The Adventures of Ichabod and Mr. Toad.
- Crates used to be able to be found across the park, name-dropping residents and locations of the land.
- Silas Crump was mentioned as the caretaker of Gracey Manor on one of these crates.
- Another mentions the Harbor House's innkeeper as being Priscilla Lapham, a character from the 1943 novel Johnny Tremaine by Esther Forbes which is set during the American Revolutionary War.
- Other parcels listed the aforementioned Legend of Sleepy Hollow characters.
- A various number of the American presidents featured in the Hall of Presidents have been referenced in Haunted Mansion connected properties and mythology.
- Andrew Jackson is frequently referenced in the Haunted Mansion's lore. This includes him having appeared on Tom Sawyer's Island which has connections to the Haunted Mansion's story, the recurring motif of Jackson's ally Jean Lafitte, and the character of Ambrose Gracey in the film continuity having been an ally of Jackson.
- In Tales from the Haunted Mansion: Volume I: The Fearsome Foursome, the mansion librarian Amicus Arcane mentions having met Abraham Lincoln.
- The bar Trader Sams' which is set in the Disney Parks mythos via S.E.A. features a photograph of the titular Trader Sam planning a South American expedition with Teddy Roosevelt.