HEADLAND HARVEST DAY FESTIVAL
2nd Saturday in October
Every 2nd Saturday in October, the Headland Chamber of Commerce sponsores the annual Harvest Day Festival around the Town Square. Festival activities include live entertainment, antique cars, rides and games for all ages, arts and crafts, cake walks, moonwalks, pony and train rides. Several local organizations have booths with lots of good food.
It's purpose is to promote our city, our local businesses and our agriculture industry. This event is a major fundraiser for a lot of local organizations and includes the Harvest Day Pageant which selects a Tiny Miss Harvest Day, Little Miss Harvest Day, Junior Miss Harvest Day, Teen Miss Harvest Day and Miss Harvest Day.
WIREGRASS ANTIQUE AND COLLECTOR CAR SHOW
1st Saturday in October
Visit one of the largest car shows in the Wiregrass Region with approximately 200 cars on display, ranging in age from "T" models to custom classics. Hosted by the Wiregrass Antique and Collector Car Club.
WIREGRASS HERITAGE FESTIVAL
Last Saturday in October
Learn how peanuts were harvested in the Wiregrass a half-century ago. Enjoy the sights, sounds and smells of cane grinding, syrup making, butter churning, basket weaving, soap making and other traditional farm activities. Plus, food, music and antique tractors and farm equipment.