Things to Do in Englewood FL in October 2026: Events Guide
October 15, 2026
October 15, 2026
On Wednesday, October 7, the blues come back to Dearborn Street. Englewood's on Dearborn has been closed since August. It reopens that night, and over the next four days the Englewood Night Market, the Waterfest Block Party and two days of offshore powerboat racing at Englewood Beach follow one after another.
The usual story is that Southwest Florida's season arrives with the winter residents. The 2026 Englewood calendar tells a different story. The season starts on a set date, early in October, and almost every event is within a few blocks of Pioneer Plaza or a short drive from Englewood Beach. The Englewood Farmers Market came back on October 1. The rest of the town fills in within ten days.
The busiest stretch is the five days from October 7 through 11. Here is how it lines up.
| Date | Event | Where | Time |
|---|---|---|---|
| Wed., Oct. 7 | Englewood's on Dearborn reopening concert, Trey Wanvig Band | 362 W. Dearborn St. | 6:30 to 9:30 p.m. |
| Thu., Oct. 8 | Englewood Farmers Market | Pioneer Plaza | 9 a.m. to 1 p.m. |
| Thu., Oct. 8 | Englewood Night Market & Music | Pioneer Plaza | 5 to 9 p.m. |
| Fri., Oct. 9 | Inflated Invitational Beach Race | Englewood Beach | Per Waterfest schedule |
| Fri., Oct. 9 | Waterfest Block Party | Dearborn Street | 5 to 10 p.m. |
| Sat. and Sun., Oct. 10 and 11 | APBA Offshore Championship | Englewood Beach | 10 a.m. to 4 p.m. |
On Thursday you can be on Dearborn Street from morning to night. The farmers market runs from 9 a.m. to 1 p.m. at Pioneer Plaza, and the Night Market opens there at 5 p.m., with live music starting at 6. Englewood Sunset Rotary runs the farmers market. The Englewood Review calls the first weeks of October a soft opening, so vendors are still being added. The market you see on October 8 will be smaller than the one you see in November.
On Friday the race crowd comes into town. The Englewood Chamber's Waterfest Block Party is free. It puts race boats on display along Dearborn Street, with food and retail vendors, drinks, and music at Pioneer Plaza. For many people, this is the closest look they will get at the boats before they head out onto the Gulf.
Englewood's on Dearborn is the clearest sign that this is a real seasonal reopening. The restaurant calls itself the "Home of the Blues." It closed for August and September in 2026 and said in July that it would be back in October. Its events page now bills the October 7 Trey Wanvig Band show as its grand reopening concert. The Englewood Review describes Wanvig as a 24-year-old Sarasota blues-rock guitarist, singer and songwriter whose shows fill the house.
The restaurant books music most nights, starting right away. Its October lineup, as posted through October 22:
The first four shows land on the same nights as the Night Market, the Block Party and the first day of racing. Music is played in three places: the front patio, the indoor dining room, and an outdoor courtyard and music hall. The kitchen serves seafood, steaks and the house schnitzel with mashed potatoes and red cabbage. For reservations, call (941) 475-7501.
On Saturday and Sunday the action moves to the beach. Englewood Beach Waterfest, a local nonprofit, runs the APBA Offshore Championship from 10 a.m. to 4 p.m. both days. The 2025 championship set a record. Forty-one boats raced over two days, and the board credited about 500 volunteers with making it work. Race Director Ralph Young has said the 2026 event will be even bigger.
This year the biggest addition is on the sand, not the water. Mote Marine Laboratory is bringing five exhibits to Waterfest's Family Conservation Center:
Other booths include Lemon Bay Conservancy, Charlotte Harbor Environmental Center, the Florida Fish and Wildlife Conservation Commission, Peace River Wildlife Center, SWFL Sea Turtle Rescue, Lemon Bay High School's AquaLab and Marine Club, and a Butterfly Encounter. Face painting, crafts and games for kids are free. Waterfest's money pays for its later spectator events and education programs about Englewood's waterways. The October 3 Paddle for the Pass cleanup, which came before race week, is part of that same effort.
The championship comes back to a beach that is only partly repaired after Hurricanes Ian and Milton. Charlotte County's disaster-recovery page for Englewood Beach and Chadwick Park lists signage, parking lot and pavement repairs, fencing, park amenities, the playground and buildings as complete. Lighting is waiting on FEMA, and equipment is waiting on insurance.
The pavilions and the sidewalks, boardwalks, piers and dock are still in design and permitting. The county's estimated completion dates for those are in August 2030. Erosion work is in planning, with an estimated start of September 1, 2026, and an estimated finish of May 1, 2027. The county lists $8,493,550 for the whole recovery project.
So the parts of the park that a spectator uses, like parking, restrooms and the playground, are listed as done. The structures that give shade and the walkways over the dunes are years away. If you are planning a long Saturday at the races, bring your own shade. The county's beach page notes that the parking lot's southern entrance reopened in April 2025 with limited spaces, and it has not posted a newer update on parking.
North of the beach, Charlotte County's Manasota Key renourishment project estimates construction from November 23, 2026, through April 30, 2027. That page still refers to a September 14 budget hearing that has already happened, so treat those dates as estimates until the county updates them. If you walk the Gulf side of Manasota Key, the shark tooth spots near Blind Pass could look different this winter.
After race weekend, Dearborn Street doesn't empty out. It moves to a steadier schedule of weekly and one-time events for the rest of the month.
Lemon Bay Playhouse, at 96 W. Dearborn St., runs "Bell, Book and Candle" from October 14 to November 1. Opening night includes a wine tasting by Southwest Florida Wine Company. On October 17 at 5 p.m., The Waverly holds its fourth Night of Empowerment fundraiser, with proceeds going to St. David's Jubilee Center's food pantry and community assistance programs.
On Tuesday, October 27, Dearborn Street's shops stay open from 4 to 7 p.m. for Discover Dearborn, a walking evening featuring the street's independent boutiques and specialty shops. On Saturday, October 31, from 5 to 7 p.m., the Old Englewood Village Association and the Rotary Club of Englewood Sunset host the 31st Annual Historic Dearborn Street Halloween Safewalk. It is free and includes a costume contest and a Haunted Hearse Museum display from the Pop Culture Antique Museum.
The weekly schedule continues past October too. The Pioneer Plaza calendar lists the next Night Markets on November 12 and December 10, and the farmers market runs every Thursday through May.
A few businesses on the street are new this year. Dr. Kim Marino-Micheel held a ribbon cutting on September 30 for Breathe Acupuncture and Wellness at 370 W. Dearborn St., Suite C, two doors down from Englewood's on Dearborn. Farther down the street, Chophouse285 opened at 285 W. Dearborn St. in January as a 10,000-square-foot steak and seafood restaurant.
From the farmers market's return on October 1 to the Safewalk on October 31, Dearborn Street has something on its calendar in every week of the month. Most of it falls between Wednesday, October 7, and Sunday, October 11.
If you're thinking about how Englewood's year-round calendar fits your own plans, whether you live near Dearborn Street now or are weighing a move closer to Lemon Bay, Julie Shaw is glad to share what she knows about the Englewood area. Let's Connect.
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