How many free evenings and mornings does Seaside put on the calendar between the first week of October and Thanksgiving weekend? Count the town's own listings and you get about two dozen. All of them happen on one lawn, and almost all of them on the same three days of the week.
That count says more about Seaside than any single event this fall. The town keeps a fixed weekly schedule at the Seaside Amphitheater, and it keeps that schedule going as the season winds down. Seaside's 45th-anniversary history puts the winter population at close to 100 residents, compared with several thousand people in spring and summer. The annual events, the Halloween night, the wine festival and the holiday parade all land on top of that weekly schedule. Through Thanksgiving, the only regular event that changes its time is the Wednesday concert, and it moves by one hour.
Wednesday, Friday, Saturday
Here is the regular week as the town currently lists it for fall.
| Day | Event | Time | Where |
|---|---|---|---|
| Wednesday | Sounds of Seaside | 5:00 to 7:00 pm in October, 4:00 to 6:00 pm in November | Seaside Amphitheater |
| Friday | Central Square Cinema | 7:00 pm | Seaside Amphitheater lawn |
| Saturday | Seaside Farmers Market | 9:00 am to 1:00 pm | The Amphitheater |
Sounds of Seaside is an outdoor set by local musicians, and the town's listing asks you to bring blankets and chairs. Central Square Cinema runs Fridays at 7:00 pm through the fall. In its August preview of the season, the town suggested getting dinner or a sweet treat from a local merchant before the movie starts. The Farmers Market runs from 9:00 am to 1:00 pm, rain or shine unless the weather turns unsafe, with local farmers, growers and artisans plus live music.
The market has already made its seasonal change. Its posted schedule runs on Tuesdays and Saturdays in June and July, then goes back to Saturdays only for August through May. So this fall's Saturday-only market is the normal schedule for ten months of the year. Summer is the exception.
Saturday mornings have been a market morning in Seaside since 1983, when co-founder Daryl Davis opened the Seaside Saturday Market. That business grew into the beachside cabanas now called Cabana by The SEASIDE Style.
The Hour That Moves
The October Sounds of Seaside lineup is Roman Street on October 7, Max McCann on October 14, a performer still listed as TBD on October 21, and BOUKOU GROOVE on October 28. Each show is listed from 5:00 to 7:00 pm.
November brings the same rotation with one new name: Max McCann on November 4, Flow Tribe on November 11, Roman Street on November 18 and BOUKOU GROOVE on November 25. The November listing moves the start to 4:00 pm and the end to 6:00 pm.
November 4 is the first Wednesday after clocks fall back on November 1. The series calls itself "an afternoon of live music," and moving it an hour earlier keeps it in the afternoon after the clock change. For anyone who walks over from a cottage after work, the November shows start before 5:00 pm, and the last one is the night before Thanksgiving.
The Friday movie and the Saturday market keep their times. Through Thanksgiving weekend, the music start time is the only change on the regular schedule.
Where The Annual Dates Fall In The Week
The annual events don't get days of their own. They fall on the same days as the regular schedule, often on the same lawn. In date order:
- Saturday, October 10 and Saturday, October 17. The town calendar lists Fall Children's Theater performances of Dragons Love Tacos from 5:00 to 6:00 pm, the evening after the morning market.
- Monday, October 12. Colombia and Company, in the SEASIDE Pop-Up District at 2236 E County Hwy 30A, holds its first-anniversary event from 10:00 am to noon. Apart from the Thursday that opens Seeing Red, it is the only weekday entry on the list that falls outside the regular week.
- Saturday, October 24. The Annual Halloweener Derby, a dachshund race and dog costume contest, takes over Central Square on a market Saturday. The event page lists 9:00 am to 1:00 pm. The town's August preview gave 10:00 am to 2:00 pm, so check the time closer to the day.
- Saturday, October 31. Halloween falls on a Saturday this year, so the market morning comes first. Halloween in Seaside then runs from 4:00 to 7:00 pm in Central Square, and this year's theme is "The Golden Ticket."
- Thursday, November 5 through Sunday, November 8. The 34th Seeing Red Wine Festival is covered in the next section.
- Sunday, November 22. Ballet Pensacola performs The Nutcracker Act II on the Amphitheater stage from 5:00 to 7:00 pm. The listing says it is free and open to the public.
- Friday, November 27. The Friday cinema slot becomes the holiday movie night, with The Grinch starring Jim Carrey from 7:00 to 8:30 pm.
- Saturday, November 28. The SEASIDE Holiday Parade & Turn on the Town runs from 3:00 to 8:00 pm, listed at 2227 E County Highway 30A, with more details still to come. The market wraps up at 1:00 pm, two hours before the parade starts.
The ballet is on a Sunday, the one day the regular week leaves open. The Grinch screening is the regular Friday movie with a holiday title. Halloween and the parade both come on market Saturdays, after the market closes.
The Ticketed Weekend On The Same Lawn
Seeing Red is the one stretch of fall with ticket prices, and it uses the same grounds as the free events. The festival's 2026 ticket and event listings lay out the weekend:
- Friday, November 6. The Al Fresco Reserve Tasting runs from 6:00 to 8:30 pm on Lyceum Lawn, with reserve and vintage pours, hors d'oeuvres and live music. Tickets are $450 plus fees.
- Saturday, November 7, morning. Battle of the Somms starts at 10:00 am. Two Master Sommeliers pick pairings for a multi-course menu and guests vote on the results, for $275 plus fees. The ticket listing puts it at the OBE Pavilion ending at noon, and the town's event page lists the Daytrader Tiki Bar ending at 12:30 pm, so confirm the venue and end time when you book.
- Saturday, November 7, afternoon. The Grand Tasting fills Central Square from 1:00 to 4:00 pm for general admission, and VIP entry starts at 12:30 pm. Tickets are $300 or $450 plus fees.
- Sunday, November 8. Celebration of Bubbles runs from 10:00 am to 1:00 pm, a sparkling-wine brunch pairing with Chef Jim Shirley, for $125 plus fees.
The festival opens Thursday, November 5, with the Vintner's Dinner at Bud & Alley's. A 30A.com event listing names Far Niente as the featured winery, with Coleen Schmalle hosting, and says the menu is still to come. Seaside's own listing gives 6:00 to 9:00 pm and the 30A listing gives an 8:00 pm start. Neither lists a price, and the 30A page says to email Bud & Alley's for tickets.
Put the festival on the regular week and it lines up with the free events. Friday's reserve tasting on Lyceum Lawn starts an hour before the regular 7:00 pm movie. On Saturday, the VIP Grand Tasting opens in Central Square at 12:30 pm, while the free market in the Amphitheater runs until 1:00 pm. For about half an hour, both are happening a short walk apart.
Why The Week Holds
Seaside was planned for this kind of week. Robert and Daryl Rose Davis founded the town in 1981, and its plan puts shops, restaurants, the beach, the Seaside Post Office and The Chapel at Seaside within a five-minute walk of every home. Robert Davis describes the result this way in the town's 45th-anniversary history:
"Of course, the most important contribution of Seaside's planning to sustainability is its walkability. Most people walk for most daily activities."
A weekly event can only run on a fixed schedule if people can reach it without planning a trip. The businesses around the lawn have worked the same way for decades. Sundog Books started in 1986 as an 8-by-12-foot plywood shack open only in summer. It is now in its 40th year, open year-round in Central Square. Modica Market has been there since 1989. Wild Nectar, the fresh-pressed juice bar and coastal kitchen on Airstream Row, had opened by mid-May and is going into its first fall.
Even this year's one infrastructure change is civic and small. A flagpole was dedicated in front of the Seaside Post Office on February 25, 2026, as part of the town's master plan. Through Thanksgiving weekend, the regular fall schedule is music on Wednesday, a movie on Friday and the market on Saturday morning, and from November 4 the music starts at 4:00 pm.
If you're thinking about how a town built around a walkable center holds its value through the slower months, Anderson Group 30A tracks Seaside block by block, from cottages near Central Square to the streets farther out. Get your custom 30A market report and see how the Seaside you live in every week compares with what's selling right now.
