The Guild's inaugural meeting was in 1984 when twenty-six die-hard quilters gathered to organize in the art room at Catamount School. Membership grew rapidly and necessitated the move to larger quarters. The first effort to raise funds for this group was a raffle quilt, and the Guild has sponsored a raffle quilt each year since. Just about every member of the Guild helps with some aspect of this project: designing, purchasing fabric, piecing blocks, and hand quilting the quilt.

The Guild published its first newsletter in 1987, an effort to keep members informed of the various activities and programs. The Guild held its first quilt show, now known as the Bennington Quiltfest, in 1994 to celebrate its 10th anniversary.