From county fair classics to clay and cocktails, wine dinners, live music, networking, and a Rocky Horror mystery dinner, here are the best ways to spend October 15 to 19 around 30A. Skim the highlights below, pick your favorites, and we’ll see you out there.

1. A Century of Fun at the Walton County Fair

Celebrate 101 years of tradition with six days of live entertainment, livestock shows, local crafts, delicious fair food, and family-friendly rides at the Walton County Fairgrounds in DeFuniak Springs.

Walton County Fair / Wednesday, October 15, 2025, from 5 p.m. – 9 p.m. @ Walton County Fairgrounds

2. Sip, Sculpt, and Support at Distillery 98

Hand-build a pink-inspired mug with artist Sarah Bumanglag while enjoying a complimentary cocktail or mocktail. Create, connect, and honor Breast Cancer Awareness Month from 5:30 p.m. to 7:30 p.m. in Santa Rosa Beach.

Cocktails & Clay: Mugs for Jugs / Wednesday, October 15, 2025, from 5:30 p.m. – 7:30 p.m. @ Distillery 98

3. Harvest Wine and Food in WaterColor

Four days of world-class wines, chef dinners, and the Grand Tasting beginning at 9:00 a.m., all benefiting children’s charities through Destin Charity Wine Auction Foundation.

9th Annual Harvest Wine & Food Festival / Thursday, October 16 to Sunday, October 19, 2025, from 9 a.m. onwards @ WaterColor Town Center + Cerulean Park

4. Business After Hours on the Greens

Connect with local professionals over drinks and light bites at 4:30 p.m. as Dixielectricar hosts an easygoing evening of networking at Santa Rosa Beach.

October 2025 Business After Hours Hosted by Dixielectricar / Thursday, October 16, 2025, from 4:30 p.m. @ Santa Rosa Golf & Beach Club

5. Electric Thursdays at SOWAL House

The Zook and Von Syndicate lights up Rosemary Beach with high-energy sets and surprise guests every Thursday at 6:00 p.m.

The Zook & Von Syndicate / Thursday, October 16, 2025, from 6 p.m. @ SOWAL House

6. Nashville Stories on the Emerald Coast

Settle in for heartfelt songwriting and versatile grooves as Tanner Gray delivers a captivating evening performance in the 30Avenue courtyard.

Tanner Gray / Friday, October 17, 2025, from 6 p.m. – 9 p.m. @ 30Avenue

7. Rocky Horror Mystery Dinner at AJ’s

Do the Time Warp while you sleuth through a live, interactive whodunit with dinner at 6:30 p.m. Costumes encouraged, PG 13, tickets include a three-course meal.

Rocky Horror Interactive Murder Mystery Dinner Show / Saturday, October 18, 2025, from 6:30 p.m. @ AJ’s Grayton Beach

8. Sunday Night Sounds at Old Florida Fish House

Settle in for crowd favorites and easygoing vibes as Jake and Aime light up the main stage from 7:00 p.m. to 10:00 p.m.

Jake and Aime Main Stage / Sunday, October 19, 2025, from 7 p.m. – 10 p.m. @ Old Florida Fish House

To keep up-to-date with daily 30A events and other fun things happening here at the beach, bookmark the 30A Events page, and download the free 30A iPhone and 30A Android apps.