Fall 2025 on 30A: The Full Lineup of Festivals, Food & Fun

When the Gulf breeze cools down just a touch and pumpkin spice sneaks back into your latte, you know fall has officially arrived on 30A. But let’s be real—this stretch of the Emerald Coast doesn’t exactly hibernate. Instead, it trades summer swims for wine festivals, pumpkin patches, and dachshunds in lederhosen.

If you’re plotting a trip (or just looking for a reason to love where you live even more), here’s your complete guide to fall events on 30A — September through November 2025.

September – October: Pumpkin Season on 30A

Pumpkin Patch at Camp Helen State Park

Oct 1–31, 2025 | Daily 9 AM–5 PM (or until sold out)
Weekends bring the extras: live music, cake walks, outdoor movie nights (yes, Hocus Pocus), and the iconic Witch Paddle on October 29.

October: Hallo-Wine, Howl-oween & Harvest Fun

• Baytowne Beer Festival
  Oct 10–11, 2025 | Sandestin
  200+ craft brews, live music, and plenty of hops-fueled cheer.

• Harvest Wine & Food Festival
  Oct 16–19, 2025 | WaterColor
  Culinary stars and boutique wineries take over the coast.

• Witch Ride
  Late October 2025 | 30A bike routes
  Costumed witches take to the streets on bikes, raising money for local charities.

• Halloweener Derby & Oktoberfest
  Oct 25, 2025 — 10 AM–2 PM | Seaside Amphitheater
  Dachshund races, a dog costume contest, and polka-fueled Oktoberfest vibes.

• Barktoberfest
  Oct 30, 2025 — 4:30–6:30 PM | Grand Boulevard
  Dogs in costumes, raffles, food, and live music.

• Trick-or-Treat in Seaside
  Oct 31, 2025 — 4–7 PM | Seaside Amphitheater
  Shops hand out candy while Wizard of Oz characters stroll by, capped with an outdoor movie.

November: Wine, Art, Races & Giving Thanks

• Rosemary Beach Uncorked
  Nov 1, 2025 | Rosemary Beach
  Gourmet bites paired with wines in an elegant outdoor setting.

• Seeing Red Wine Festival
  Nov 6–9, 2025 | Seaside
  Open-air tastings, chef dinners, and live music.

• Flutterby Arts Festival
  Early Nov 2025 | Watersound Origins
  Family-friendly art fest celebrating monarch butterflies.

• Alys Beach Crafted
  Nov 12–16, 2025 | Alys Beach
  Artisan cocktails meet a chic makers market.

• Sparkling Wine & Holiday Lights
  Nov 22, 2025 | Baytowne Wharf
  Holiday kickoff with bubbly, twinkle lights, and festive cheer.

• Grayt Jackelope Trail Race
  Nov 22, 2025 | Grayton Beach State Park
  Scenic coastal trail run through Grayton’s natural beauty.

• Sandestin Turkey Trot
  Nov 23, 2025 | Sandestin Resort
  5K and 1-mile fun run to pre-burn that pie.

• 30A Thanksgiving Day Races
  Nov 27, 2025 | Along 30A
  Choose your challenge: 10K, 5K, or fun runs with those Gulf views.

Season-Long & Recurring Events

• Monarch Art Trail | Fall 2025 | Inlet Beach & 30A
  Stroll past butterfly-inspired sculptures and murals.

• 30A Art Walk | First Fridays (Sep–Nov 2025)
  Galleries and live music across the coast.

• Grayton Beach Wine Walk | Third Thursdays (Oct & Nov 2025)
  Local wines, art, and good vibes.

The Fall Vibe on 30A

• October = pumpkins, puppies in costumes, and witches on bikes.

• November = wine glasses clinking, art festivals, and guilt-free pie (because you ran it off in a Turkey Trot).

FAQs About Fall on 30A

Q: Is fall a good time to visit 30A?
A: Absolutely. The crowds thin, the weather is perfect, and event season is in full swing.

Q: Are these events family-friendly?
A: Most of them! Pumpkin patches, art fests, and trick-or-treating are perfect for kids, while the wine festivals and beer fests are adults-only fun.

Q: Do I need tickets in advance?
A: For big-name festivals like Harvest Wine & Food or Seeing Red Wine, yes — grab them early. Smaller events like art walks are more casual.

Q: What’s the dress code?
A: Think coastal casual with a seasonal twist. Sundresses and sandals in October, maybe a light sweater by late November evenings.

Ready to Fall for 30A?

Whether you’re planning a weekend wine escape or looking for a coastal home base to soak it all in, fall is the perfect time to experience 30A living.

👉 Start your 30A home search today or request a complimentary home valuation.