Weekend Events for December 19th - 21st
What’s Happening in Pensacola This Weekend?!
December 19th –21st, 2025 – Fun for Families, Couples & Visitors
The holiday season is in full swing in Pensacola, and this weekend brings a mix of festive performances, downtown holiday experiences, sports, and local favorites. Whether you’re exploring downtown with family or planning a night out with friends, here are some great events to check out.
Winterfest – Downtown Pensacola
Location: Plaza Wonderland – Government & Palafox Street
Dates: Friday, December 19 | Saturday, December 20 | Sunday, December 21
Time: Preshows begin around 5:00 PM nightly
Enjoy the popular holiday trolley experiences including The Polar Express, The Grinch’s Merry Match, and the Peanuts Gang Tour. Downtown lights, music, and seasonal décor make this a must-see event. Free preshows take place nightly, with ticketed trolley tours running throughout the evening.
Helpful Tips:
Free parking is often available on North Palafox Street or at Commendencia Landing with trolley access nearby.
Dress warmly, as December evenings can be cool.
Arrive early if you plan to catch the free preshows before your scheduled trolley time.
Ballet Pensacola Presents: The Nutcracker
Location: Saenger Theatre – Downtown Pensacola
Dates: Friday, December 19 | Saturday, December 20 | Sunday, December 21
Showtimes:
Friday at 7:00 PM
Saturday at 12:30 PM and 7:00 PM
Sunday at 11:00 AM and 4:00 PM
Enjoy this timeless holiday classic performed by Ballet Pensacola in the historic Saenger Theatre. This production is a seasonal favorite for both locals and visitors.
Helpful Tip: Plan to arrive about 30 minutes early to enjoy the theater and get settled before the show begins.
Pensacola Ice Flyers vs. Huntsville Havoc
Location: Pensacola Bay Center
Date: Saturday, December 20
Time: 7:05 PM
Spend Saturday night cheering on the Pensacola Ice Flyers during an exciting home game. This is a great option for families, groups, or a fun date night.
Parking Tip: Bay Center parking can fill up quickly. Arriving 45 minutes early is recommended.
Gallery Night Pensacola
Location: Downtown Palafox Street and surrounding galleries
Date: Friday, December 19
Time: 5:00 PM – 9:00 PM
Gallery Night is a popular downtown tradition featuring local artists, gallery exhibits, live entertainment, and extended shopping hours. It’s a great way to start your weekend and support the local arts scene.
Holiday Shopping and Local Pop-Ups
Throughout downtown Pensacola, local shops and galleries often host holiday pop-ups and extended shopping hours leading up to Christmas. While schedules may vary, strolling downtown is a great way to find unique gifts and enjoy the festive atmosphere.
Helpful Tip: Check individual business social media pages for last-minute pop-up events and special promotions.
Weekend Tips and Local Insights
Getting Around:
Downtown parking is managed through the ParkMobile app. Parking a few blocks away and walking can help avoid congestion during evening events.
Family-Friendly Planning:
Winterfest events and Nutcracker performances are especially popular with families. Consider earlier showtimes if attending with younger children.
Dining and Coffee Stops:
Downtown Pensacola offers plenty of dining and coffee options, making it easy to plan meals around your weekend activities.
Photo Opportunities:
The Winterfest plaza and Saenger Theatre provide great backdrops for holiday photos. Layered outfits work best for changing temperatures.
Weekend Wrap-Up
From holiday performances and downtown festivities to sports and local art, Pensacola has something for everyone this weekend. Plan ahead, arrive early when possible, and enjoy everything our community has to offer.