The holiday season is just around the corner, and Pensacola has so much festive fun in store for everyone! From markets and parades to Winterfest and holiday treats, this season is packed with exciting events for all ages. Here’s your guide to some of the best winter events happening in Pensacola this year.
November 15: Winterfest Begins!
Winterfest Opening Night
Pensacola’s Winterfest is back, transforming downtown into a holiday wonderland! Watch as historic streets light up with festive displays, and kick off the holiday magic on select nights from November 15 through December.
📍 Downtown Pensacola
🕒 Select nights starting Nov 15
Gallery Night
On November 15, stroll down Palafox Street during Gallery Night for art, music, and festivities. It’s the perfect opportunity to enjoy the beginning of Winterfest with holiday lights and a festive downtown atmosphere.
📍 Downtown Pensacola on Palafox Street
🕒 5:00 PM
November 16: A Day of Holiday Markets and Festivities
Rosie’s Antique Emporium Holiday Open House
Rosie’s is hosting a Holiday Open House with unique holiday decor, gifts, and in-store sales. Enjoy light refreshments as you browse this beloved spot for holiday treasures!
📍 3929 W. Navy Blvd., Pensacola
🕒 10:00 AM - 5:00 PM
Paul Christmas Market and Bake Sale
Get into the holiday spirit with this charming market and bake sale. Perfect for finding unique gifts and homemade treats!
📍 St. Paul Catholic Church, 4142 Hyde Park Rd, Pensacola
🕒 9:00 AM - 3:00 PM
Pensacola Maker Faire
Support local artisans and makers at the Maker Faire, featuring unique crafts, goods, and artwork at Museum Plaza.
📍 Museum Plaza, 201 Zaragoza St, Pensacola
🕒 10:00 AM - 4:00 PM
Pensacola Fall Food Truck Fest
Grab a bite (or two) from a variety of food trucks while enjoying the fall weather at Community Maritime Park.
📍 Community Maritime Park, 301 West Main St, Pensacola
🕒 11:00 AM - 7:00 PM
O'Riley's Winter Brewfest
Warm up with seasonal brews at O'Riley's Winter Brewfest. Enjoy tastings and special winter beers at this cozy holiday event.
📍 O'Riley's Irish Pub, 321 S. Palafox St, Pensacola
🕒 5:00 PM - 9:00 PM
November 17: Photos with Santa Begin!
Winterfest: Photos with Santa
Starting November 17, meet Santa himself in his Winterfest Plaza sleigh every Friday and Saturday! Starting December 20, Santa will be available every day until Christmas Eve.
📍 Winterfest Plaza, 223 S. Palafox Place, Pensacola
🕒 Fridays: 4:30 PM - 8:30 PM
🕒 Saturdays: 10:00 AM - 8:30 PM
🕒 Starting Dec 20: Daily, 4:30 PM - 8:30 PM (Christmas Eve until 7:30 PM)
Weekly: Palafox Market Holiday Market
Every Wednesday from November 20 to December 18, MLK Jr. Plaza hosts the Palafox Holiday Market, featuring local vendors with holiday gifts, festive foods, and seasonal decor.
📍 MLK, Jr. Plaza, Downtown Pensacola
🕒 Wednesdays, 4:00 PM - 8:00 PM
November 30: Holiday Indoor Market
Check out the Holiday Indoor Market at Sanders Beach Ballroom with over 40 local vendors offering handmade items, perfect for unique holiday gifts!
📍 Sanders Beach Ballroom, Pensacola
🕒 10:00 AM - 3:00 PM
December Highlights
December 1: Pensacola Community Outdoor Flea Market
Find treasures, shop for gifts, or clear out some clutter at the second annual Outdoor Flea Market. Free entry for shoppers and proceeds go to charity!
📍 Location: Community Maritime Park
🕒 10:00 AM - 5:00 PM
December 4-8: Snowball Derby
Racing fans won’t want to miss this 300-lap super late model stock car race at Five Flags Speedway. A Pensacola tradition, the Snowball Derby promises adrenaline and excitement!
📍 Five Flags Speedway, Pensacola
🕒 All-day events (times vary)
December 6 & 7: Mutts & Mimosas
Bring your furry friends to Calvert’s in the Heights for paw painting, mimosas, and a chance to celebrate the holiday spirit with your pets.
📍 Calvert’s in the Heights, Pensacola
🕒 11:00 AM
December 14: Pensacola Christmas Parade & Santa Paws and Pints
- Santa Paws and Pints
- Bring your pets to Gary’s Brewery & Biergarten for holiday fun, drinks, and food trucks.
- 📍 Gary’s Brewery & Biergarten
- 🕒 12:00 PM - 4:00 PM
- Pensacola Christmas Parade
- Enjoy the annual Christmas Parade downtown, with floats, marching bands, and plenty of holiday cheer for the whole family.
- 📍 Downtown Pensacola
- 🕒 5:30 PM
Winterfest: December 20 - 24
As the holidays draw near, Winterfest goes daily! Experience the lights, music, and festive charm in downtown Pensacola every night leading up to Christmas.
📍 Downtown Pensacola
🕒 Daily starting Dec 20
Pensacola’s winter season is packed with events that bring our community together in holiday cheer! From holiday markets and parades to Winterfest and food festivals, there’s something for everyone. Mark your calendars and join us in celebrating the most wonderful time of the year! 🎄✨