Towle was born in Chicago, Illinois in 1967. He attended Oak Park and River Forest High School (’85). Towle holds two Bachelor of Arts degrees from Vassar College (’89) in Art History and English.
While in Provincetown he produced poetry, and worked as a pool boy and a bartender at The Boatslip Resort. After moving to New York in 1992, he became a bartender and later a manager at the 1990s Manhattan gay bar Splash.
From 1998 to 2002, Towle served as the editor in chief of Genre magazine,[5] and editor at large for The Out Traveler,[6] an American gay travel quarterly.
Towle's poetry appeared in The Yale Review (May 1991),[7]Ploughshares (Winter 1992–93),[8][9][10]The Paris Review in 2000,[11] and in Poetry Magazine (July 1988,[12][13] November 1988,[14] February 1991,[15] May 1997,[16] and July 1999).[17]
Towle founded the website Towleroad in 2003[18] and left in 2021[19][20][21] to focus full time on a career in visual art.
In June 2024, Towle held his first solo painting show at Provincetown Commons in Provincetown, Massachusetts.[22]