"Tickets go on sale exclusively to Rosemary Beach property owners and typically sell out." That line comes from the FAQ for Rosemary Beach Uncorked, and it explains how the town's fall calendar works. Between now and Thanksgiving, each big event in Rosemary Beach has a hard limit: a three-hour afternoon on one green, a tasting that sold out with property owners first in line, and 3.5 hours on Thanksgiving morning when nobody can drive on Scenic Highway 30A.
Saturday, October 24: Two Windows, One Afternoon
Halloween weekend is two days after this post goes up, and it runs in two stages. The Rosemary Beach Property Owners Association has scheduled Trick-or-Treat Around Town for Saturday, October 24, from 10 a.m. to 5 p.m. Participating merchants will hand out candy and goodies across Town Center during those hours.
The Kids Halloween Bash on the East Long Green is shorter, from 2 to 5 p.m. So the candy route runs for seven hours across the shops and the bash gets the last three on one lawn. A morning loop through Town Center and an afternoon on the green are two separate outings on the same day. The POA's only stated dress code is "Costumes encouraged."
The Halloween Bash is open to anyone who shows up. The next big event is not.
Saturday, November 14: Owners Get First Access to Uncorked
Uncorked turns 15 this year. It runs Saturday, November 14, from 1 to 4 p.m. in Barrett Square. General admission is $225 and the VIP Experience is $350. The event homepage already lists it as sold out. A time-stamped waitlist is the only way in, and any tickets that come back go to the public first-come, first-served.
General admission covers eleven food and wine tasting stations from the Merchants of Rosemary Beach, plus entertainment, a swag bag and an etched Uncorked wine glass. The 2026 ticket listing names the participating restaurants, and nearly every one is a regular stop in town:
- Amavida Coffee
- Blue By Night
- Edward's
- Cowgirl Kitchen
- La Crema Tapas & Chocolate
- Restaurant Paradis
- CK's Feed & Supply
- Havana Beach Bar & Grill
- Pescado
- Tahona Tacos & Tequileria
Guests visit the restaurants in any order, and local retailers pour more wine at "SIP Stops" along the way. In practice, the tasting route runs through the same Town Center storefronts that hand out Halloween candy three weeks earlier.
What the New VIP Tier Adds
This year is the first with a VIP option, and its extra space sits north of the square. VIP holders get the Audi Lounge inside Town Hall and a VIP tent on Town Hall Green. Both stay open an extra hour, until 5 p.m., for VIP holders only. The perks include signature cocktails and a mimosa bar, winemaker Tom Garrett pouring Dakota Shy Winery, food from Chef Rob McDaniel of Helen in Birmingham, Alabama, a caviar tasting with caviar nachos, live music and a goodie bag. November 14 is also an SEC Saturday, and the Audi Lounge has big-screen TVs reserved for VIP guests.
Where the Money Goes
The 2026 beneficiaries are Caring & Sharing of South Walton and Children's Volunteer Health Network. According to the Uncorked FAQ, Caring & Sharing provides crisis relief in Walton County and serves more than 900 families each month. CVHN has served more than 23,000 children in Walton and Okaloosa counties since 2005, providing over $10 million in health care at no cost to families. CVHN comes up again twelve days later.
Thursday, November 26: The Highway Closes for the Turkey Trot
On Thanksgiving morning, the 30A 10K Thanksgiving Day Races close the road itself. According to the race organizers, Highway 30A will be closed to all traffic on Thursday, November 26, 2026, from 7:00 to 10:30 a.m. The closure runs from East Water Street in Rosemary Beach, where the start and finish lines are, to the 10K turnaround at Bridge Lane just east of The Big Chill. Watersound Parkway will also close from its intersection with 30A north to the Camp Creek Inn entrance for the 5K route.
If you're roasting a turkey in Rosemary Beach that morning, the timing works out like this:
- Wednesday, Nov. 25, 11 a.m. to 6 p.m.: packet pickup at The Big Chill. There's no race-day packet pickup.
- Thursday, 7:00 a.m.: 30A closes to all traffic.
- 7:30 a.m.: the 10K starts.
- 7:35 a.m.: the 1-mile fun run starts.
- 9:30 a.m.: the 5K starts, with Watersound Parkway in use.
- After the races: the awards ceremony and post-race party in Barrett Square.
- 10:30 a.m.: 30A reopens.
Online registration closes November 24 at 11:59 p.m. Central. The post-race party includes a DJ, local vendors, breakfast, and a complimentary mimosa and Bloody Mary bar. Every finisher gets a race shirt and medal.
This year the 10K is also the RRCA Florida State Championship 10K. The RRCA will present its own awards to the overall male and female finishers, the 40+, 50+ and 60+ divisions, and the adaptive male and female champions. The organizers say Southern Living has named the race one of the top 10 turkey trots in the South, and they describe the course as flat, past dune lakes and South Walton's architecture.
The race is run by a 501(c)(3) nonprofit, and it reports raising more than $1 million to date for local charities. This year's charity partners are Children in Crisis, Bailey Brigade, Children's Volunteer Health Network and Habitat for Humanity of Walton County. So CVHN benefits from both the tasting in Barrett Square on November 14 and the race that finishes near the square on Thanksgiving morning.
The Windows at a Glance
| Date | Event | Where | Window | What limits access |
|---|---|---|---|---|
| Sat., Oct. 24 | Trick-or-Treat Around Town | Town Center | 10 a.m. to 5 p.m. | Participating merchants only |
| Sat., Oct. 24 | Kids Halloween Bash | East Long Green | 2 to 5 p.m. | Afternoon only |
| Sat., Nov. 14 | Rosemary Beach Uncorked | Barrett Square | 1 to 4 p.m., VIP until 5 | Owner-first sales, now sold out |
| Wed., Nov. 25 | 30A 10K packet pickup | The Big Chill | 11 a.m. to 6 p.m. | No race-day pickup |
| Thu., Nov. 26 | 30A 10K, 1-mile and 5K | East Water Street to Bridge Lane | 30A closed 7:00 to 10:30 a.m. | Road closed to all traffic |
After the Race: Last Year's Holiday Dates
The holiday season starts right after the race weekend, but its 2026 dates haven't appeared on the POA's events calendar yet. Last year's calendar gives a good idea of what to expect. The 2025 Tree Lighting Ceremony was on November 28, the night after Thanksgiving, in South Barrett Square, and Santa arrived that evening. A local holiday guide published this month lists this year's lighting for Friday, November 27, around 6 p.m. in South Barrett Square, the same slot right after Thanksgiving. Check that date against the official calendar before you make plans.
In 2025, Breakfast with Santa was at Town Hall on November 29, and S'mores & Santa with professional photos was in South Barrett Square on December 20. Last season, Walton County Tourism also listed special Rosemary Beach farmers markets on Tuesday, November 25, Wednesday, December 24, and Wednesday, December 31, from 9 a.m. to 1 p.m. at 28 N. Barrett Square. The regular Sunday market runs year-round, 9 a.m. to 1 p.m., according to the POA's market page. Those Sunday mornings continue after all three fall events are done.
If you own in Rosemary Beach and want to know how weekends like these affect rental bookings, guest access and the time of year buyers like to visit, the team at Sold in Paradise follows this calendar closely. Find Your Slice of Paradise and book a free 30A market consultation before Thanksgiving weekend.
