Holidays on the Boulevard

What’s Coming Up at Grand Boulevard Town Center

The holidays in South Walton, Florida, are nothing short of magical, where twinkling lights meet Gulf breezes and every community adds its own charm to the season. From tree lightings and festive markets to elegant dinners and New Year’s celebrations, there’s always something to gather for. Mark your calendar and make the most of this sparkling season at Grand Boulevard Town Center in Sandestin® with events that capture the joy, community, and coastal spirit of the holidays.

November 21 | 5:00–6:30 PM

Hometown Holiday Parade & Celebration

On Friday, November 21, Grand Boulevard transforms into a winter wonderland, sparkling with thousands of dazzling white lights. The Holiday officially begins with the unveiling of the lights and a festive parade down the Boulevard featuring Grand Boulevard’s tenants, local nonprofits, community leaders, and more. And of course—don’t miss the magical arrival of Santa Claus!

November 28–December 21

Annie at Emerald Coast Theatre Co.

Leapin’ lizards! Join your favorite redheaded orphan Annie, Daddy Warbucks, and the eternally grumpy Miss Hannigan for this musical feel-good story of finding home. With hits like “You’re Never Fully Dressed Without a Smile,” “It’s a Hard Knock Life,” and “Tomorrow,” you will experience the magic of the holidays and the spirit of generosity that always comes this time of year. Thursdays through Saturdays at 7 PM; Sundays and Wednesdays at 2 PM; Visit EmeraldCoastTheatre.org for the full schedule and to get your tickets!

December 2 | 4–6:30 PM

Festival of Trees at Grand Boulevard

The Festival of Trees is a beloved Grand Boulevard tradition, taking place each year in Grand Park. This year’s celebration will be held on Tuesday, December 2—the Tuesday after Thanksgiving and also the National Day of Giving. The event is open to the public and features a festive atmosphere with piped holiday music, hot chocolate, cookies, and the official tree judging. Guests can purchase a $5 voting bell to cast their vote for their favorite tree for the People’s Choice Award. Winners, including the judges’ selections, will be announced at 6:30 PM, and the beautifully decorated trees will remain on display in Grand Park through Christmas. Visitors are encouraged to stroll through the park, enjoy the magical holiday setting, and learn about the mission of each participating organization.

December 6

All Day Sip ’n’ Shop

Celebrate the season at our Holiday Sip ’n’ Shop all day long on Saturday, December 6. This is the perfect opportunity to enjoy a day of holiday shopping while taking advantage of special promotions, exclusive discounts, and fun giveaways from participating businesses. Be sure to enjoy the live music at Sunset Shoes!

December 5–27 | Fridays & Saturdays, 4–7 PM

Holiday Horse-Drawn Carriage Rides

Experience the magic of the holidays with complimentary horse-drawn carriage rides through Grand Park! One beautifully decorated carriage will be stationed in front of Krewe Sunglasses, offering rides on Fridays and Saturdays in December, leading up to Christmas, as well as Monday, December 22, and Tuesday, December 23.

December 18–23 | 4–7 PM

Coastal Christmas Celebration Events in Grand Park

• Santa’s Arrival & Photos

Welcome Santa to Grand Park and capture the magic with your own photo by the beautifully decorated Grand Boulevard Christmas Tree. (Please note: photographer not provided.) No carriage rides or Santa Photos on Sunday, December 21—the horses and Santa are resting!

• Holiday Musical Children’s Performances

Each evening, delight in a live children’s holiday show presented by Emerald Coast Theatre Company from 5–5:45 PM (Sunday’s performance time TBA).

And, of course, throughout the holiday season, the shops and galleries of Grand Boulevard transform into a treasure trove of gift ideas. Whether you’re searching for a timeless piece of jewelry, cozy apparel, unique artwork, or a touch of elegance for the home, the community’s shops make gifting feel effortless. Explore curated picks from beloved retailers and national brands, each offering something as thoughtful and beautiful as the Emerald Coast itself.

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Visit GrandBoulevard.com to learn more.