Tinsel Town
Outdoor Movies in the Park: Home Alone & Home Alone 2
Bring your lawn chairs, friends and family!! We will be having a double feature yet again this year! Home Alone will begin playing at 5:30pm with Home Alone 2 following.
Christmas Cookie Crawl
Visit each participating business and fill your cookie box! Boxes will be available on the night of the event under the gazebo on the square. Visit the following businesses to pick up a cookie:
TBA
Christmas Photos in front of the "McCallister Mansion"
The Headland Public Library will transform into the Kevin's home and fortress.
Schedule of Events
5:00pm Cookie Crawl Begins
5:00pm - 7:00pm Photos at the Mansion
5:30pm Movie Start Time
Annual Christmas Parade
The City of Headland will light the Christmas tree at the gazebo at 6:00pm on the downtown square. The Grand Marshal will lead the parade through the downtown area followed by bands, floats, queens, dignitaries, horses, Santa Claus, and CornDodgers Farm's candy cannon. The parade line-up will be at Douglas Park starting at 4:30pm and line up ends at 6:00pm. The Christmas Parade is sponsored by the Headland Area Chamber of Commerce and City of Headland. Participants need to complete the online registration by Monday, December 1st. For more information, contact the Chamber by email at director@headlandal.org.
Entry Fees:
Chamber Member $10
Non-member $20
Float/Semi-truck $30
Group Fee $30
Christmas Under the Oaks
Under the Oaks is Brought to you by:
Sponsors
Join us for Under the Oaks on the Square in Downtown Headland on the third Friday in April, May, and June, and now with a concert on the second Friday of December! This annual concert series has become extremely popular in the seven years that it's been around. Drawing concert goers from both near and far, this keystone event for the City of Headland now boasts over 12,000 attendees a year! The concert is free, all you need is a lawnchair or blanket. There are always food trucks as well as our downtown restaurants and businesses being open. Don't miss out on all the fun; everyone will be there!
Schedule of Events
December 12th - The Dylan Kelley Band
Food Trucks
December 12th
History of Under the Oaks
Under the Oaks music event, launched in 2019, has grown into one of the premier events in the Wiregrass area. This annual concert series takes place from April to June, featuring a wide variety of musical performances set beneath the city’s beautiful oak trees. The event offers a mix of genres from folk and jazz to rock and blues, attracting visitors from near and far. In addition to the spring and summer concerts, a special Christmas edition is held each December, bringing festive music and holiday cheer to the community. Under the Oaks continues to foster a sense of connection and celebration, showcasing talent, food vendors, and family-friendly activities in a welcoming and vibrant atmosphere.
Under the Oaks FAQs
Let it Glow
Southeastern Cooling INC
Downtown Headland shines even brighter during the holiday season thanks to our annual Let It Glow Christmas Light Competition! Local businesses deck out their storefronts, windows, and displays with dazzling lights and festive décor, bringing extra sparkle to our community. Visitors are encouraged to stroll or drive through town to enjoy the creativity and holiday spirit on display, then cast their votes for their favorite entries. It’s a fun and friendly way for our businesses to spread cheer and show off their Christmas spirit while making Headland truly glow for the holidays!