Get ready to put on your boots and raise a glass, Englewood. Lemon Bay Sunrise Rotary can’t wait to welcome you to the 3rd Annual Small Town Boots & Brews Country Music Festival, and this year will be the best yet.
Mark your calendars for Saturday, March 21, 2026, and plan to immerse yourself in an all-day celebration of country music, all in the heart of Englewood’s Pioneer Plaza on Dearborn Street. There’ll be dancing, great food, top-notch country music and ice-cold drinks; everything you need for a memorable day and a great cause.
Here’s the lineup:
A full day of live music from some of the best local and regional country artists, covering everything from classic country to Southern rock and honky-tonk jams.
Music Schedule:
10:00 AM—11:30 AM Everett Ferrell
11:45 AM—1:15 PM Flatwater
1:30 PM—3:30 PM Crossfire Creek
3:45 PM—5:15 PM Hunter Creek Band
5:30 PM—7:30 PM The Winters Brothers Band
7:45 PM—9:45 PM Pure Country of Southwest Florida
Whether you’re a country diehard or just here for live music and good times, you’ll find something to love. Spend your day dancing under the open sky or just sit back, relax, and enjoy the show.
Now, let’s talk about the food and drinks. Full-service bars will abound at Pioneer Plaza, serving cold beer, unique craft brews, frozen cocktails, and much more. If you get hungry (and you will), check out the food trucks and local vendors serving everything from classic BBQ to home-style Southern comfort food.
Of course, there’s line dancing and other activities to keep the crowd moving, and the festival’s open to all ages. It’s the kind of event you can bring your kids, friends, and neighbors, because everyone’s welcome.
But Small Town Boots & Brews isn’t just music and fun. When you walk through those gates, you’re helping Lemon Bay Sunrise Rotary support the Englewood community. Every entry donation goes straight into local programs, like scholarships, Meals on Wheels, supplies for schools, and so much more.
Chris Anders from Englewood Lemon Bay Sunrise Rotary puts it best: “Every year, the music just gets bigger and better. We’re bringing six talented bands, some fresh faces and returning favorites. The level of talent is high, especially for an event supported by donations.”
He adds, “All proceeds go right back into Englewood. The money funds scholarships, Meals on Wheels, school programs—you name it. It’s a chance to have a great day and really support the people in our own community.”
This isn’t just any old music festival; it’s Englewood’s festival. Bring your friends, bring your family, and make a day of it. See you at the Small Town Boots & Brews Country Music Festival.
For more information, go to englewoodfestival.com.
The event is free, with a suggested $3 donation; kids 12 and under are free.
