Winter Park Christmas Markets 2025

Step into a winter wonderland at the Festival of Trees, a cherished Orlando holiday tradition. This year's theme, 'A Season of Celebration,' brings to life over 50 dazzling designer-decorated trees, festive wreaths, and charming gingerbread creations. Discover unique gifts in...

Jingle Eve returns for its 20th year, marking the official start of the holiday season in Orlando. This vibrant festival transforms Ivanhoe Village with festive cheer, featuring a lively street party with music, local artisans, and a variety of food...

Get into the holiday spirit at the annual Holiday Milk Mart! This vibrant street festival transforms The Milk District into a shopper's paradise, featuring over 300 local artists, makers, and food vendors. It's the perfect opportunity to find unique, handmade...

Step into a festive medieval kingdom at the Enchanted Knights: Winter Bazaar. This holiday Renaissance Faire invites you to explore a marketplace brimming with the magic of the season. Discover unique treasures from local artisans, be captivated by talented performers,...

Experience the magic of the holidays at the Oh, What Fun! Holiday Festival in Lake Nona Town Center. This annual event transforms the area into a winter wonderland with nightly snowfalls, festive decor, and a calendar packed with family-friendly activities....

Experience Cracker Christmas, a vibrant two-day celebration of Florida's pioneer heritage held annually on the first full weekend of December. This beloved event at Fort Christmas Historical Park brings history to life with engaging live demonstrations, a bustling craft fair...

Step back in time at the 44th Annual Cracker Christmas, a vibrant two-day celebration of Florida's pioneer heritage. This beloved event at Fort Christmas Historical Park features live historical demonstrators, a bustling craft fair with authentic handmade goods, and a...

Experience the magic of the holiday season with the Holiday Home Tour & Magical Marketplace. Wander through stunning, seasonally decorated homes in Celebration, and discover unique treasures at the Magical Marketplace. The event also features an exclusive Sparkle Soirée VIP...

Step into a winter wonderland at the Christmas Winter Festival in DeLand. This community celebration brings together local artisans and festive cheer for a delightful holiday experience. Browse unique crafts, soak in the seasonal atmosphere, and enjoy a day of...

Discover a vibrant winter market at Playalinda Brewing Company, featuring over 35 local vendors offering unique crafts and holiday shopping opportunities. Enjoy live music, delicious brunch specials, and festive drinks. Engage in creative workshops like Bonsai & Cheers, or test...

Leesburg's Christmas Festival & Parade transforms Towne Square into a winter wonderland. Families can enjoy live music, a free ice skating rink, photos with Santa, and unique holiday shopping. The day culminates with the 58th Annual Leesburg Christmas Parade, a...