[4] "While working odd jobs to make money, we held our first auditions outdoors in Glover Park and started improvisatory workshops in the auditorium of the HHS building.

During this period the company worked with the Pennsylvania Avenue Development Corporation to acquire space for and to outfit a new theatre.

People can enjoy Woolly who are Democrats or Republicans, liberals or conservatives, because we're trying to come at audiences from unexpected points of view.

[11] In 2018, Woolly Mammoth hired Maria Manuela Goyanes as its artistic director, succeeding founder Howard Shalwitz.

[12] The theatre's education and outreach programs include "Pay-What-You-Can" (PWYC) performances providing access to all residents regardless of economic means,[13][14] and "Playmaking," which pairs students with professional playwrights.

[15] "Woolly D.C." is a program where a neighborhood joins to create an original production based on an issue of common community concern, and there are internships, workshops, and theater classes, including a partnership with the University of Maryland, College Park.