It became notable for its association with the journalist and Woody Creek resident, Hunter S. Thompson, who frequented the establishment on a near-nightly basis for late lunches when in town.

[8] In December 2007, Flying Dog announced that it was closing the Denver brewery and would produce beer solely in its Frederick facility.

Flying Dog was also experiencing its strongest growth to date and could surpass Denver production levels by concentrating operations in Maryland.

[12] In 1983, Stranahan, Richard McIntyre and ten close friends decided to climb the K2 mountain in the Himalayas, the second highest peak in the world.

In 1990, Thompson introduced Stranahan to Ralph Steadman, who went on to create original artwork for Flying Dog's beer labels in 1995.

His first label artwork was for the Road Dog Porter, a beer inspired and blessed by Thompson who wrote a short essay about it titled "Ale According to Hunter".

Flying Dog Brewery is noted for using the unusual art of Ralph Steadman, known as the illustrator of Thompson's works, on its labels.

In October 2013, in honor of the relationship between Steadman and Thompson, Flying Dog Brewery created an exhibition titled "The Gonzo Collection", featuring reinterpretations and responses to Steadman's work by several notable international artists, including Bob Dob, Nathan Spoor, Justin Bua, Michael Owen, Nanami Cowdry and Tatiana Suarez.

The album was released at the first annual Frederick Fall Fest,[17] a mid-sized music festival presented by Flying Dog.

[19] In 2011, with help from the Center for the Defense of Free Enterprise, Flying Dog filed suit against the 2009 decision, citing freedom of speech.