Cantonment Christmas Events & Things to Do 2025

Step into a world of holiday magic with 'A Chocolate Covered Christmas Carol.' This unique theatrical event reimagines the timeless tale with a delightful, sweet twist. Prepare for a festive and heartwarming performance that brings Charles Dickens' classic story to life in a way you've never seen before.

Ballet Pensacola presents the enchanting holiday classic, The Nutcracker. This beloved performance brings Tchaikovsky's magical score to life with breathtaking choreography and dazzling costumes. Join Clara on her whimsical journey through a land of snow and sweets, featuring world-class dancers.

Get ready to paint Pensacola red and green at the 13th annual Santa Pub Crawl! This festive event invites participants to don their best Santa outfits for a lively crawl down Palafox Street. Starting at O'Riley's Irish Pub, the crawl includes stops at various local establishments, offering exclusive deals and...

Get ready for the most magical shopping night of the season! The 9th Annual Holiday Haul on Palafox transforms Downtown Pensacola into a festive wonderland. Discover unique holiday collections, enjoy live music, and snag great deals as local shops host a street-wide open house. Don't miss Santa's visit and the...

Experience the enchantment of Pensacola Winterfest, a beloved holiday tradition. Journey through classic Christmas tales on themed trolley tours like the Polar Express and A Christmas Carol. Meet Santa and the Grinch for photos, enjoy festive preshows, and witness magical snowfall in Plaza Wonderland. It's a heartwarming celebration perfect for...

Get ready for the annual Beulah Christmas Parade! This beloved community event marks the start of the holiday season with a festive procession. Mark your calendars for this cheerful gathering.

Experience the magic of the holiday season by visiting Santa Claus at Cordova Mall. This festive event offers a wonderful opportunity for families to create lasting memories and capture cherished photos with Santa. Enjoy the cheerful atmosphere as you prepare for the holidays.

Get into the holiday spirit at the Pensacola Elf Parade! This festive event kicks off the season with a lively parade and fun contests. Dress in your best elf outfit, an ugly holiday sweater, or decorate a wagon to join the fun. Santa himself will announce the winners before the...

Step into a world of holiday enchantment with the Mistletoe Magic Tour. This enchanting trolley ride takes you on a journey through classic Christmas love songs, serenaded by the spirit of legendary artists. It's the perfect way to cozy up and celebrate the most wonderful time of the year with...

Ring in the New Year with an unforgettable plunge into the Gulf of Mexico at the Flora-Bama Polar Bear Dip. Join thousands of friends, both old and new, for this exhilarating tradition. Participants who brave the chilly waters at high noon are rewarded with a free draft beer and a...