The Winchelsea Festival is a family event held each year at the Winchelsea Sports Centre. The Festival includes: a Wood Chop event, Market, Food and Wine Stalls, Ute Show, Ferret Cup, Fleece Show, and continuous entertainment and children's activities. There are Emergency Services Displays, Spinning and Weaving, Stud Sheep, Vintage Vehicles, Model Boat Displays and novelty events. For the kids the emphasis is on "touch and feel" country life experiences.

The GMRG presence is made up of a Military Vehicle Display, Weapons, Field Kitchen, Uniforms and Personal Equipment, all in the surrounds of a WW2 period style encampment.