Your 30A and Destin Fall Event Guide

July 14, 2025

If you’re craving a getaway that’s equal parts relaxing and refined, fall is the perfect time to visit the Emerald Coast. With festivals, art shows, and scenic races, the season is filled with experiences geared toward travelers who appreciate great food, good company, and a slower pace. Here’s your guide to the best fall events in Destin and 30A for couples, friends, and anyone looking to unwind in style!

Raise a Glass: Wine Tastings, Craft Beer and Food Festivals

Celebrate the season with flavorful wine walks, craft beer fests, and food events highlighting the region’s local ingredients. Here are a few of our favorites:

Baytowne Beer Festival

October 10-11: Sample over 200 domestic and international brews in the heart of Sandestin.

Grayton Beach Wine Walk

October 16-17: Sip on a cabernet and meet local artists at this laid-back Santa Rosa Beach tasting event, which occurs on the third Thursday of every month.

Harvest Wine and Food Festival (WaterColor)

October 16-19: A four-day celebration of food and wine featuring celebrity chefs and boutique wineries.

Rosemary Beach Uncorked

November 1: An upscale block party with fine wine and gourmet bites, all set in a charming community with cobblestone streets.

Seeing Red Wine Festival

November 6-9: Sip and socialize in charming Seaside at this beloved annual tradition.

Alys Beach Crafted

November 12-16: An artisan showcase celebrating craft cocktails, fine spirits, and makers of all kinds, set against the stunning backdrop of this stunning community.

Sparkling Wine & Holiday Lights

November 22: Kick off the season with bubbly and bright lights at Baytowne Wharf, featuring over 30 champagnes and hors d’oeuvres in a festive waterfront setting.

Art and Culture: Galleries and Creative Events

Discover the area’s thriving art scene, showcasing local artists and skilled creators of all kinds!

Monarch Art Trail

Follow a self-guided trail on 30A of striking outdoor sculptures and murals inspired by the monarch butterfly’s annual fall migration.

30A Art Walk

Explore local galleries, meet regional artists, and enjoy live music during this celebration of creativity along the coast on the first Friday of every month.

Get Moving: Bike Rides and Fitness Events

Take advantage of the cooler weather, get outdoors, and join in a fall fitness event. Here are some fun ones you won’t want to miss:

Witch Ride

October 24: A costumed bike ride tradition with flair—yes, capes and hats included.

Grayt Jackelope

November 22: A fun, coastal trail race through Grayton Beach State Park with scenic views and good vibes.

Sandestin Turkey Trot

November 23: Start your holiday weekend on the move with this festive 5K and 1-mile fun run through the Sandestin Golf & Beach Resorts.

30A 10K, 5K, and 1-Mile Fun Run

November 27: One of the coast’s most beloved Thanksgiving Day traditions, with race options for every pace and incredible views at every turn.

Savor the Fall Flavors: Exceptional Dining Experiences

You’ll find many standout restaurants known for their seasonal menus, exceptional ambiance, and thoughtful service, ideal for intimate dinners and quiet celebrations (age restrictions may apply). Here are some must-tries:

Pescado

Sip rooftop cocktails and enjoy coastal cuisine with Gulf views that go on for days in Rosemary Beach.

Beach Walk Cafe

Enjoy an intimate dining experience in Destin right on the water—the perfect setting for romantic evenings.

Restaurant Paradis

This ultra-stylish restaurant in Rosemary Beach pairs perfectly with fresh Gulf seafood and fine wine in a warm, sophisticated setting.

Where to Stay Near Fall Events in 30A and Destin

Craving quiet mornings, breezy bike rides, and evenings that end with a glass of wine and a Gulf view? Scenic Stays offers a range of beautiful vacation rentals with luxurious bedrooms, spa-like bathrooms, and cozy balconies, all near the best fall events in Destin and 30A!Sign Up for Vacation Deals

Your 30A and Destin Fall Event Guide

Raise a Glass: Wine Tastings, Craft Beer and Food Festivals

Harvest Wine and Food Festival (WaterColor)

Art and Culture: Galleries and Creative Events

Get Moving: Bike Rides and Fitness Events

Savor the Fall Flavors: Exceptional Dining Experiences

Where to Stay Near Fall Events in 30A and Destin

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