The Legend of Sleepy Hollow connects with the American Romantic period in its use of the staple themes of Gothic literature, much similar to actual Romantics such as Poe, Wilde, Stoker, Shelley, etc.

The typical themes of Romantic/Gothic literature include:

• The use of the supernatural
• Dark atmospheres symbolizing a fear of the unknown
• The inevitability of fate and death
• A path leading to tragedy
• Nostalgia and Fear
• The battle of good versus evil

Whether Irvin was an actual Romantic or not usually does not impede that his works would possess qualities of another period or style. Sleepy Hollow follows the same lines of form and depth as Dracula, Frankenstein, Dorian Gray, and most of Poe's works.

Washington Irving served as a kind of role model and mentor for many of the American Romantics writing in the late 1800's--chiefly among them Nathaniel Hawthorne and Edgar Allan Poe. Although not exactly a Romantic himself, Irving paved the way for many who were and serves as a kind of "bridge" between the Romantics and those that came before.

In "The Legend of Sleepy Hollow" we see the ideas and themes that eventually become hallmarks of the Romantic movement. Namely, the embracing of individualism and the rejection of strict religious intellect. The focus is much more on emotional response, rather than logic.