Winterfest Wonderland

Twinkling Lights and Trolley Delights

by Morgan Cole

Kicking off November 21 and running through Christmas Eve, Pensacola’s beloved Winterfest event series will return, transforming downtown Pensacola into a winter wonderland featuring festive trolley tours, holiday performances, thousands of dazzling lights and more.

Established in the 90s as a neighborhood gathering and trolley ride, Winterfest has grown to become a month-long annual tradition best known for its trolley performance tours, where guests hop aboard decorated trolleys and experience a series of interactive performances along a two-mile route with a cast of Christmas characters.

This cherished annual celebration brings family-friendly fun and holiday cheer to downtown Pensacola with live performances, an Elf Parade, interactive trolley tours, Santa and his reindeer and a myriad cast of characters.

“We look forward to bringing holiday magic to the Gulf Coast every year and this will be our biggest, most spectacular Winterfest ever,” Winterfest Founder Denise Daughtry said.

Santa and his friends will visit Winterfest on select nights beginning November 21 to welcome the arrival of the Winterfest Express Electric Train to downtown Pensacola. This kid-sized train seats 24, and will run downtown each night of Winterfest throughout the Christmas season. Tickets are $5 per-person, and can be purchased online through the Winterfest website.

“This year we’re adding two new trolley tours, starting with the Peanuts Tour, where kids (and kids at heart) can team up with Charlie Brown and friends on a quest to discover the true meaning of the season and search for the perfect tree,” Winterfest Performance Tours Coordinator River Dakota said. “Couples are also in for a treat this year aboard the Mistletoe Magic Tour—a romantic, musical journey filled with laughter, champagne and timeless holiday hits from legends like Elvis and Eartha Kitt.”

Winterfest offers opportunities to have your photo taken with Santa and the Grinch, ride on the Polar Express and many more holiday themed festivities. Seasonal extras include nightly street theater on the historic courthouse steps and a life-sized gingerbread house rest stop, complete with hot cocoa and fresh-baked gingerbread cookies.

This year’s festivities will once again include the popular Elf Parade on November 28 at 2 pm, providing an opportunity for the entire family to join in the fun as hundreds of revelers riding strollers, skateboards and wagons to follow Santa on a merry path through downtown Pensacola.

During the parade lineup, Santa himself will host a jolly costume contest— awarding prizes for Biggest elf ears, best costume, best-decorated stroller, best-decorated wagon, ugliest sweaters and most festive skateboarder. Santa will announce the costume contest winners from each category just before the parade rolls out, and each winner will lead their section of the parade.

Also new this year—to celebrate the return of Snoopy and the Peanuts gang—is a special contest and Elf Parade group for the best dressed and decorated dog in a stroller. The winner will march at the head of the section with Snoopy.

“What started as a small community tradition has grown into a beloved celebration that draws families from across the region to downtown Pensacola. This year’s event will be our biggest and most spectacular Winterfest ever—filled with new experiences, dazzling lights and the joyful spirit that makes downtown Pensacola shine during the holidays,” Daughtry said.

This year’s Winterfest is set to be bigger, brighter and more magical than ever, offering a full season of magic, memories and holiday joy for all ages.

Winterfest tours and photos with Santa take place in Plaza Wonderland at the corner of Government Street and Palafox Place. Snow and music starts at 5:30 pm on Fridays and 5 pm on Saturday and Sunday on all tour nights.

Tickets are on sale now, and can be purchased online at pensacolawinterfest.org. Prices for performance tours and photo sessions vary by date, so be sure to check out the calendar for details.

From twinkling lights to trolley delights, here’s a highlight of this year’s new and returning performance tours.

Polar Express Tour

December 5–7, 12, 14 & 19-2

This magical tour immerses you in the classic story of The Polar Express with visits from your favorite characters. The tour begins with a musical show on the courthouse steps, where tap-dancing servers will give everyone a cup of hot cocoa. The conductor of the Polar Express will lead everyone aboard an open-air tram to embark along a 25-minute journey to a life-size steam engine. During the ride, you’ll be delighted by musical performances and exciting effects along the way. Tickets start at $15 for adults and $9 for kids

The Scrooge Tour

December 21, 22, 23 & 24

For this 25-minute tour, the Scrooge tour takes you through the classic tale of A Christmas Carol, where guests will encounter the stingy businessman Ebenezer Scrooge, his dead business partner Jacob Marley and the ghosts of Christmas past, present and future. Experience this spooky Christmas tale as you, along with Ebenezer, learn to hold Christmas in your heart and keep it all the year. Tickets start at $20 for adults and $16 for kids.

The Grinch’s Merry Match

December 5–7, 12, 14 & 19–24

Feel your heart grow three sizes larger when you join the Grinch’s Merry Match. Hop aboard the Grinch’s brand-new trolley and sing along to classic Christmas songs as you find yourself at the heart of a timeless love story. The Grinch’s Merry Match tour will introduce you to a cast of classic Seussian characters such as Thing 1 and Thing 2, the Mayor of Whoville, Martha May Whoveir and, of course, the Grinch himself. Tickets start at $20 for adults and $9 for kids.

Mistletoe Magic

December 7 & 14

Brand new this year, this dazzling experience is led by the charming guide Bing Crosby, who will take you on a musical tour into a world of your favorite holiday hits. This tour is perfect for couples who want to cozy up and sip champagne under the mistletoe and sing along to their favorite seasonal sensations with actor-singers portraying icons like Elvis Presley, Eartha Kitt, Nat King Cole, Brenda Lee and more. Tickets start at $16 for adults and $13 for kids.

The Peanuts Tour

December 5–7, 12, 14 & 19–24

Join Charlie Brown and the Peanuts gang as they search for the perfect Christmas tree. As you journey through festive forests and snowy streets, you’ll discover plenty of Christmas cheer and adventure. Perhaps you, and even Charlie Brown too, will find out what makes Christmas the happiest time of the year. Tickets prices start at $15 for adults and $9 for kids.