October has arrived in Naples and Southwest Florida, and with it comes the first real stir of season. Big concerts, candlelit music, a stone crab tradition in Everglades City and a dog friendly morning at Naples Botanical Garden all land on the same weekend.
A Big Weekend for Live Music
Friday night, Grammy, ACM and CMA Award winner Ashley McBryde brings her Into The Wild Tour to Barbara B. Mann Performing Arts Hall in Fort Myers at 8 p.m., blending country and rock 'n' roll with support from Colton Bowlin. Saturday may be the biggest night of the fall so far. Los Tigres Del Norte play Hertz Arena in Estero at 8 p.m., One Night in Memphis brings a rock 'n' roll tribute to Artis Naples' Hayes Hall at 7:30 p.m., and Florida Repertory Theatre hosts Fleetwood Mac by Candlelight at 6 p.m. For something with a little more fire, Love Flamenco performs at the Music & Arts Community Center at 4 and 7:30 p.m.
Stone Crab Season Begins in Everglades City
Saturday morning, Camellia Street Grill in Everglades City hosts the annual Blessing of the Stone Crab Fleet at 10 a.m. This longtime tradition brings the community together along the Barron River for a blessing of local boats and crews, followed by live music and plenty of stone crab. Nearby, the Florida Alligator Festival runs from 10 a.m. to 5 p.m. at Skunk Ape Headquarters, making it easy to turn the drive into a full day.
A Sunday Morning for You and Your Dog
Naples Botanical Garden hosts Paws for Peace in the Garden on Sunday from 8 to 11 a.m. The Shelter for Abused Women & Children and the Patty Baker Humane Society Naples will be on site in recognition of Domestic Violence Awareness Month, with adoptable dogs, a doggy photo booth, treats and more. If you prefer to start the day by the water, Seaside & Sunrise Pilates meets on Bonita Beach at 8 a.m.
Comedy, Soccer and Fall Fun
Comedian Vinny G performs at Off the Hook Comedy Cafe Friday and Saturday at 6 and 8 p.m., with Tia Kemp on Sunday. FC Naples hosts the New York Cosmos at Paradise Coast Sports Complex Saturday at 7 p.m. Farmer Mike's Annual Fall Festival is open in Bonita Springs every weekend through October 31, and Naples Art Picnic hosts Flower Pumpkin Art at Birch Lane Sunday afternoon. Farmers markets run Saturday and Sunday in Naples, Bonita Springs, Fort Myers, Sanibel and beyond.
Why This Weekend Matters If You Are Considering Naples or Southwest Florida
Weekends like this one show what life here actually looks like as the season begins. A community that blesses its fishing fleet, fills its concert halls and spends Sunday morning in the garden with its dogs. It is not a show put on for visitors. It is simply how people live here, week after week.
If Naples has been on your mind, whether as a second home, a future move, or a place you are still getting to know, I am always happy to be a resource. Reach out anytime, or sign up for This Week in Paradise, my weekly guide to living, playing and owning in Southwest Florida, delivered to your inbox every Friday.
Diane Harris, Realtor and Luxury Properties Specialist
Serving Naples, Bonita Springs, Estero, Marco Island, Collier County, Lee County and the surrounding Southwest Florida area




