30A Fall Festivals and Events Guide: Everything You Need to Know 🍂🎡
When the summer crowds fade and the breeze turns just a little crisper, 30A transforms into a laid-back, festival-filled paradise. Fall here isn’t just about pumpkin spice — it’s all about food, wine, live music, and celebrating the slower pace of coastal living. 🍷🌾
Whether you’re visiting for a long weekend or spending the whole season soaking up the sunshine, here’s your guide to the best fall events on 30A — from wine strolls to artsy markets and everything in between.
1. Harvest Wine & Food Festival – WaterColor 🍷🍤
When: Late October
Where: Cerulean Park, WaterColor
This signature fall event is a must for foodies and wine lovers. Hosted by Destin Charity Wine Auction Foundation, it features over 250 wines, gourmet bites from top chefs, and a laid-back lawn party vibe.
Best for: Girls’ getaways, couples, wine lovers
Pro tip: Snag VIP tickets early — they always sell out!
Bonus: Proceeds go to local children’s charities 💕
2. Flutterby Arts Festival – Watersound Origins 🎨🦋
When: Early November
Where: Watersound Origins
A sweet, family-friendly event celebrating the migration of the monarch butterfly, this festival is full of live music, local art booths, crafts for kids, and food trucks.
Best for: Families, artists, and creative souls
Look for: Face painting, butterfly crafts, and live performances
Vibe: Wholesome and whimsical
3. Baytowne Beer Festival – Sandestin 🍻🍂
When: Mid-October
Where: The Village of Baytowne Wharf
Sip your way through 200+ craft brews from around the country in a charming waterfront setting. There’s live music, laid-back vibes, and plenty of food vendors to soak it all up.
Best for: Beer lovers, couples, friend groups
Bring: Your ID, comfy shoes, and a big appetite
Tip: Check for Friday night pre-party events and tastings
4. 30A Half Marathon & 5K – Gulf Place 🏃♀️🍁
When: October
Where: Starts and ends at Gulf Place
Lace up for a scenic run along 30A’s stunning coast, then stick around for the post-race party with music, food, and fun. Proceeds support local non-profits and veterans’ causes.
Best for: Active travelers, fitness lovers
Good to know: There’s a fun run for kids too!
Bonus: Race shirts and medals are actually cute
5. Seaside Farmers Market Fall Saturdays 🌾🛍️
When: Saturdays, year-round
Where: Seaside Amphitheater
Fall brings cooler mornings and pumpkin-themed goodies to this beloved market. Stroll with a coffee, grab a homemade pastry, and browse seasonal produce, handmade crafts, and local art.
Best for: Morning people, slow travel lovers
What to try: Local honey, farm eggs, fall-themed baked goods
Pro tip: Get there early for the best picks + easy parking
6. Seeing Red Wine Festival – Seaside 🍇🎉
When: November
Where: Throughout Seaside
This iconic four-day event is all about vino, coastal cuisine, and Seaside charm. Think open-air tastings, winemaker dinners, and ocean breeze vibes with a wine glass in hand.
Best for: Couples, wine lovers, girlfriend getaways
Tip: Dress up! It’s a little more upscale, but still beach-casual
7. Monarch Art Trail Celebration – Inlet Beach 🦋🎨
When: Fall kickoff event + art installation season
Where: Inlet Beach multi-use path
Celebrate the monarch migration and public art with this scenic, interactive trail featuring butterfly-inspired sculptures by regional artists. Great for walking, biking, and photos.
Best for: Nature lovers, art fans, cyclists
Family fun: Bring kids for a scavenger hunt along the trail
8. Halloween on the Green – Rosemary Beach 🎃👻
When: Late October
Where: North Barrett Square, Rosemary Beach
Trick-or-treating, a costume contest, and outdoor movie night under the stars? Count us in. This is a great event for families staying in Rosemary Beach during spooky season.
Best for: Families, little goblins, fall photo ops
Bring: Costumes, blankets, and a camera for cute pics
Tips for Enjoying Fall Events on 30A 💡🍂
✔️ Book accommodations early — festivals = busy weekends
✔️ Bring layers — mornings and evenings can be breezy
✔️ Stay hydrated — even in fall, that Florida sun shines bright
✔️ Follow event pages on Instagram for real-time updates
✔️ Try something new — paddle in the morning, sip wine by sunset
Final Thoughts 🎶🌞
Fall is one of the best-kept secrets on 30A. The beaches are quieter, the weather is dreamy, and the local events bring out the best of food, art, music, and community. Whether you’re running a 5K or sipping chardonnay under the stars, there’s a fall festival here with your name on it.
Need help finding the perfect weekend to visit, book a cozy stay near your favorite event, or plan a full fall itinerary? I’ve got you! Just ask 🍁📍✨
