Headland Harvest Festival is Brought to you by:
Sponsors
Join us for the Annual Headland Harvest Festival a cherished community celebration that brings together the best of local culture, entertainment, and family fun! This year’s event promises to be bigger and better than ever, with a delightful mix of activities and attractions that cater to all ages. This fun-filled event takes place downtown in and around Headland's beautiful city square on October 10th & 11th. The day is a tribute to local farmers and the harvest season. It includes a car show, tractor show, children’s games and rides, arts and crafts, food vendors, and live entertainment throughout the day.
Schedule of Events
September 28, 2026 Harvest Festival Pageant 6:00pm
October 12, 2026 Harvest Run 5K and Fun Run 7:30am
October 10, 2026 Harvest Day Car Show 8:30 am
October 10, 2026 Harvest Day Tractor Show 8:30 am
October 10, 2026 Harvest Day Arts & Crafts Festival 9:00am-3:00pm
Harvest Day
Headland Harvest Day began over five decades ago as a small community gathering featuring a domino competition, bike races, an art show, and performances by local talent. While the event has grown significantly since its beginning, it remains true to its roots by celebrating the spirit and traditions of our community.
Explore our vibrant square filled with unique arts and crafts from local artisans. This is the perfect opportunity to find one-of-a-kind gifts, home decor, and handmade treasures that showcase the creativity of our community.
Indulge in all your favorite fair foods, from funnel cakes and corn dogs to cotton candy and kettle corn. With a wide array of delicious treats, you’re sure to satisfy your cravings and discover new favorites.
Harvest Pageant
Monday, September 28th, 6:00 pm Headland High School Auditorium
$5 to enter
Register
Tuesday, September 8th, 4:00PM-6:00PM Headland Chamber office 25 Grove Street
The Headland Area Chamber of Commerce office is located inside the Headland Municipal Complex. The pageant registration fee is $30 per contestant.
One winner will be awarded in each division. Photogenic is a separate category and DOES NOT count towards the total score. The photogenic fee is $5, picture optional.
Harvest Run 5K
Come join us for a beautiful sunrise run in Headland, AL! This is our 18th year of our 5k and Fun Run! This mostly flat course is easy and enjoyable for all age groups.
Harvest Tractor and Car Shows
Our Harvest Festival Car Show is back! We will give away over 20 awards between our Stock and Modular categories. We'll have door prizes and a 50/50! Register in advance or at Kingdom College. Entrants will line their vehicles down Main Street towards all of the action of Harvest Day! Don't miss showing off your beautiful ride!
October 10, 2026
Registration begins at 8:30am
$20 Entry Fee
We are looking forward to hosting our fourth tractor show at the Headland Harvest Festival. We hope that you will help us grow our tractor show! Registration is free! We will award 1st, 2nd, and 3rd in three divisions (small, medium, and large classes) and a People's Choice Award.
October 10, 2026
Registration begins at 8:30am