"The idea of Seaside," Robert Davis has said, "came from my memories of childhood summers near here, staying in simple cottages some distance from the beach, walking each morning to a corner store or cafe for breakfast or lunch, spending evenings on the porch waiting for the house to cool and listening to family members tell stories."
Seaside turns 45 this year, and its fall calendar is a good test of that idea. From early October through New Year's Eve, nearly everything the town puts on happens in its shared outdoor spaces at no charge: the Amphitheater, Central Square and the Christmas Village. Seaside sells tickets to its own lawns on only one weekend, November 5 through 8, when the Seeing Red Wine Festival takes over Lyceum Lawn and Central Square.
A smaller town to share
Seaside describes itself as a town of roughly 350 cottages and about 150 outbuildings. It puts its winter population at close to 100 residents, rising to several thousand in spring and summer. Fall is when that number starts dropping. The programming stays steady anyway, and it stays in the same spaces the town plan put at its center. Shops, restaurants, the beach, the Seaside Post Office and The Chapel at Seaside all sit within a five-minute walk of every home.
Some of the oldest pieces of the calendar go back to the town's first years. Daryl Davis started the Seaside Saturday Market in 1983. Sundog Books opened on Memorial Day Weekend in 1986 in an 8-by-12-foot plywood shack and at first stayed open only in summer. In its 40th year, it is open year-round from Central Square. A bookstore that started out closing every fall and now stays open through it fits the season Seaside is planning for.
The weekly rhythm, and the hour it gives up in November
Three recurring events carry the fall. The Seaside Farmers Market runs every Saturday from 9 a.m. to 1 p.m. at the Amphitheater. Central Square Cinema continues Fridays at 7 p.m. through the fall, with seating on the lawn. Sounds of Seaside fills Wednesday afternoons with local musicians at the Amphitheater.
Sounds of Seaside starts earlier in November. October shows run 5 to 7 p.m. Starting November 4, the series moves an hour earlier, to 4 to 6 p.m. Seaside's November listing places it in Central Square, where the Amphitheater sits. Here is the full posted lineup through November:
| Wednesday | Performer | Hours |
|---|---|---|
| Oct. 7 | Roman Street | 5–7 p.m. |
| Oct. 14 | Max McCann | 5–7 p.m. |
| Oct. 21 | To be announced | 5–7 p.m. |
| Oct. 28 | BOUKOU GROOVE | 5–7 p.m. |
| Nov. 4 | Max McCann | 4–6 p.m. |
| Nov. 11 | Flow Tribe | 4–6 p.m. |
| Nov. 18 | Roman Street | 4–6 p.m. |
| Nov. 25 | BOUKOU GROOVE | 4–6 p.m. |
The other fixtures are already in place for the season. On Monday, October 12, Colombia & Company marks its first anniversary in the Pop-Up District from 10 a.m. to noon. The shop's address is 2236 E County Hwy 30A.
Three Saturdays on the square
The weekly rhythm is easiest to see on three consecutive-season Saturdays in Central Square. Two of them are free.
The first is October 24, the Annual Halloweener Derby. It opens with a dog costume contest for pups of every size, followed by the dachshund race. Seaside's event page lists a 9 a.m. start for the costume contest. Seaside's fall guide and the ticketing page give different hours, so check the event page the week of the race before you go.
The second is October 31. Halloween in Seaside runs from 4 to 7 p.m. in Central Square, and this year's theme is a Golden Ticket candy wonderland, with decorated storefronts and trick-or-treating through town.
The third is November 7. That afternoon Central Square becomes the Grand Tasting of the Seeing Red Wine Festival, and the square requires a ticket.
The weekend the lawns are ticketed
The 2026 Seeing Red Wine Festival is the event's 34th year. Seaside Arts & Entertainment Corp. organizes it. Over four days, it moves through the same spaces that host the free calendar the rest of the season. Prices below are face value as posted on BigTickets, before fees.
- Thursday, Nov. 5, 6–9 p.m. The Vintner's Dinner at Bud & Alley's opens the festival with wine and a curated menu. Seaside says more details are coming and has not posted a price.
- Friday, Nov. 6, 6–8:30 p.m. The Al Fresco Reserve Tasting on Lyceum Lawn features vintage and reserve wines poured by winemakers, culinary offerings and live music, at $450.
- Saturday, Nov. 7, 10 a.m. In Battle of the Somms, two Master Sommeliers pair wines with a multi-course meal and guests vote on their favorite pairings, at $275. The event is run in partnership with Ithaka Hospitality Partners. Seaside lists it at The Daytrader, while the ticketing description names OBE Pavilion.
- Saturday, Nov. 7, 1–4 p.m. The Grand Tasting in Central Square brings wines poured by winemakers and vintners from around the world, food from local chefs and eateries, and live music. General admission is $300, and VIP tickets are $450, with 12:30 p.m. entry to a VIP lounge in Central Square.
- Sunday, Nov. 8, 10 a.m.–1 p.m. Celebration of Bubbles pairs Champagne, Cava and Prosecco with Chef Jim Shirley's brunch. It takes place in a tent on Lyceum Lawn, costs $125 and is ticketed separately from the general admission and VIP packages.
If you plan to attend more than one event, BigTickets also sells bundles. Al Fresco plus Saturday general admission is $650, and Al Fresco plus Saturday VIP is $900. The free calendar barely pauses for the festival. The Wednesday concert on November 4 falls the evening before the Vintner's Dinner, and Flow Tribe plays the Amphitheater on November 11, three days after the festival ends.
The restaurant in both calendars
The Daytrader Tiki Bar & Restaurant was selected for the 2026 Michelin Guide. It sits at the entrance to Coleman Beach Pavilion, at 2236 E County Hwy 30A, Units 4 and 5. The guide singled out its boiled peanuts finished with red Hawaiian sea salt and its tuna crispy rice. Chef Nikhil Abuvala is behind the restaurant, and in a joint statement he and Hannah Grace Abuvala credited the recognition to their team and "our guests and community for supporting us since day one." If Seaside's listing holds, the same room that serves a sloppy koa on an ordinary Tuesday hosts two Master Sommeliers on the festival Saturday.
Airstream Row has added Wild Nectar, a juice-and-bowls kitchen owned by Kolbi Amos and Hayden Shaw. Seaside reported it open in a May 17, 2026 article. Its current listing gives the address as 2235 E County Hwy 30A and the phone number as (850) 660-5246. Modica Market is still at 109 Seaside Central Square, where Charles Modica Sr. and his wife, Sarah, opened it in 1989.
After the glasses are cleared
Once the festival tents come down, the calendar goes back to free events in the same spaces and runs through the end of the year:
- Nov. 22, 5–7 p.m. Ballet Pensacola performs Act II of The Nutcracker on the Amphitheater stage, free and open to the public. Seaside's event page lists this date, and an older calendar blurb that says November 24 is out of date.
- Nov. 27, 7 p.m. Central Square Cinema shows The Grinch.
- Nov. 28, 3–8 p.m. The SEASIDE Holiday Parade and Turn on the Town, at 2227 E County Highway 30A.
- Dec. 5 and 6. The SEASIDE Holiday Market fills Central Square, 9 a.m. to 4 p.m. on Saturday and 10 a.m. to 4 p.m. on Sunday.
- Dec. 12–20, 4–6 p.m. Photos with Santa in the Christmas Village are complimentary.
- Dec. 31, 4–9 p.m. The New Year's Eve Celebration in Central Square includes live music, family activities and fireworks over the Gulf.
Seaside added a new civic marker this year as well. On February 25, 2026, the Seaside Post Office raised the American flag on a newly installed flagpole, with the Walton County Sheriff's Office Honor Guard and a dedication from the Davis family and the Seaside Community Development Corporation. The post office is next to Sundog Books, so parade night and the holiday market both pass right by it.
If your Seaside cottage will be empty for part of this calendar, or you want to know how festival weekends and holiday dates affect its value as a rental or a sale, Stroop Group can help with home watch while you're away and a free home valuation whenever you're ready.
