The original building housing the Ugly Oyster was founded in the 1700s and is the oldest pub in Berks County. After many years in many different forms, owner Glenn Rigg acquired the bar in 1991. Working in the restaurant business for many years, Glenn had long been interested in creating a bona fide Irish Pub when he learned about the Guinness Irish Pub concept program. To claim authenticity, interested pub owners must take formal classes through the Guinness Brewery and must meet specific guidelines.

After taking these classes at the Guinness Brewery in Ireland, Glenn undertook the massive rework required to create an authentic pub, a redesign so extensive that only a small portion of the backbar remains from the former interior.

On St. Patrick's Day 2000, the Ugly Oyster Drafthaus opened in its current form to rave reviews and loyal and growing clientele.