The League's first conference was held in 1944, when UVM was the location for the Summer Institute. Featuring workshops by respected professional writers, editors, and publishers, the Summer Institute lasted until about 1970. It would be 1990 before the League sponsored another conference. The three-day Dorothy Canfield Fischer Conference was held under the League's auspices from 1990 to1993, spun off into a private endeavor, and ended in 1997.
In 2008, the League held a "sold-out" Writers Meet Agents event in July, launching a new conference era for the group. The 2010, the "Timeless Craft, Timely Skills" Conference hits the boards in July, with Vermont author Chris Bohjalian as keynote speaker, sharing the bill with agents, editors, and presenters from around New England and the mid-Atlantic seaboard.
An addition to hosting seasonal meetings and conferences, the League has a history of supporting members who want to organize workshops on specific aspects of writing and publishing. Past topics have included writing fiction, non-fiction book proposals, building characters, writing for the sports market, writing for children, and giving readings. Like all League events, these workshops are open to the public.