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. 

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:

October 10, 2025

7:00-10:00pm Harvest Street Dance

The Street Dance, a cherished tradition of Headland Harvest Day that made its triumphant return four years ago, is an evening event that transforms the downtown square into a lively celebration. As the sun sets, the square comes alive with the sounds of live music, courtesy of this year's featured band, The U.S. Band. Dylan Kelley will kick off the evening at 6:30pm and warm up the crowd.  The atmosphere is electric, with people of all ages dancing and enjoying the music under the stars. For those seeking a more exclusive experience, the VIP section offers a private dance floor and high-top tables, providing an elevated view of the festivities, and reserved parking. The Street Dance is a highlight of Harvest Festival, bringing the community together for a night of fun, music, and dancing in the heart of downtown.

October 11, 2025

7:30am Harvest Run 5K and Fun Run

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.

Click here to Register

8:30 am Harvest Day Car Show and Tractor Show

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!

$20 Entry Fee

We are looking forward to hosting our third 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.

9:00am-3:00pm Harvest Day Arts & Crafts Festival

Date: October 10 & 11, 2025

Location:

Downtown Headland and City Square
Headland, AL 36345

Click here for more information