Founded in May 2003 by Justin Krebs and Matt O'Neill at Rudy's Bar and Grill in the Hell's Kitchen neighborhood of New York City, it has, as of March 2008, 240 chapters in forty-five states, plus Washington DC, Vancouver, Calgary, Buenos Aires Argentina and Melbourne Australia.
The first chapter outside of New York was formed when a member of the original group moved to San Francisco; the later growth of Drinking Liberally is partly due to the influence of left-leaning political blogs, which spread the word and encouraged people outside of the New York City area to start their own chapters.
Chapters of Drinking Liberally meet at a regular bar or pub, and at a regular time each week or month, to enable members to discuss liberal and progressive politics in a friendly environment.
Drinking Liberally has also served as a place for progressive networking and as a place for local and state-level politicians to recruit volunteers and generate support for their campaigns.
In the early stages of Drinking Liberally's growth, attendees were predominantly young (between twenty and thirty years old); as the organization has expanded and received greater media coverage, a much wider range of ages can be found at any particular meeting, and some chapters have been founded by people well over the age of thirty.