Orange Beach Senior Center Chili Cook-Off Returns Oct. 28 as ‘Trail Boss’ Defends His Title

ORANGE BEACH, Ala. — The Orange Beach Senior Center is turning up the heat this week for its second annual Chili Cook-Off, an evening of friendly competition, live music and free food where the people in the crowd get to decide who makes the best chili.

The cook-off is set for Wednesday, Oct. 28, from 4:30 to 6:30 p.m. at the Orange Beach Senior Center. Seven competitors, including six senior care and health organizations, will go head to head for the top prize.

The crowd is the judge

Unlike competitions that rely on a panel of experts, this cook-off puts the decision in the hands of the people who show up. Attendees will taste the entries and vote for their favorite bowl of chili.

That format makes the event as much about community as it is about cooking. Competitors get the chance to meet residents face to face, and guests get to sample a variety of recipes in one place.

‘Trail Boss’ returns to defend his title

Last year’s winner is back and ready to defend his crown. Brad Johnson, who competes under the nickname “Trail Boss,” took home the trophy at the inaugural cook-off. This year he will face six challengers, each hoping to claim the title of best chili maker.

The competitors

The full list of chili competitors includes:

• “Trail Boss” Brad Johnson — defending champion
• SouthernCare
• Haven Memory Care, LLC
• Live Oak Village Independent and Assisted Living
• HealthActions Physical Therapy
• Baldwin Hearing Center
• Access Home Health and Hospice

Each competing organization represents a different part of senior care and community health in the Orange Beach area, from memory care and assisted living to physical therapy, hearing care, home health and hospice. The mix of participants reflects the wide network of services available to older residents along the Gulf Coast.

For many older adults and their families, events like this offer a relaxed way to learn about local providers before they need them. It can be easier to ask questions about home health, hearing care or assisted living over a bowl of chili than in a doctor’s office or during a stressful moment.

Live music and free grilled cheese

The evening will also feature live entertainment. Musician Truman Holland will perform during the competition.

And for anyone who wants something to go with their chili, Cheesy Grillers will be on site offering free grilled cheese sandwiches to all attendees. Chili and grilled cheese is a classic fall pairing, and organizers say the free food is part of what makes the evening a fun night out.

A hub for older adults

The Orange Beach Senior Center serves as a gathering place for older adults in the area, offering programs, activities and social events throughout the year. Senior centers like this one play an important role in helping residents stay active, connected and engaged, which research has long linked to better health and well-being as people age.

Events such as the Chili Cook-Off bring residents and local businesses together for friendly competition and community pride. They also give newcomers a chance to see what the senior center offers.

Orange Beach, like much of coastal Baldwin County, is home to a large and growing population of retirees and older adults, many of whom moved to the area for its beaches, mild winters and quality of life. That growth has helped fuel demand for senior services and community programming.

Tips for chili cook-off guests

• Arrive early. The event runs for two hours, and the most popular pots can go quickly.
• Pace yourself. With seven entries to taste, small samples make it easier to compare.
• Keep notes. Jot down what you like about each chili before casting your vote.
• Stay for the music. Truman Holland will be playing throughout the evening.
• Ask questions. Many competitors are local providers who can share information about their services.

Part of a busy fall in Baldwin County

The Orange Beach cook-off is one of several chili events around Baldwin County this fall. The Robertsdale Car Show & Chili Cook-Off returns Nov. 14 to raise money for the Robertsdale High School band. Fall in coastal Alabama tends to bring a full calendar of festivals, fundraisers and community gatherings as the weather cools.

If you go

• What: Second annual Orange Beach Senior Center Chili Cook-Off
• When: Wednesday, Oct. 28, 2026, 4:30 to 6:30 p.m.
• Where: Orange Beach Senior Center, Orange Beach
• Competitors: Seven, including defending champion Brad “Trail Boss” Johnson
• Judging: Attendees vote for the best chili
• Music: Truman Holland
• Food: Free grilled cheese from Cheesy Grillers

For more information, contact the Orange Beach Senior Center or the City of Orange Beach.