Downtown Crowd


Classic Holiday Stories Come to Life in Downtown Pensacola

It is once again that time of year when the storage bins filled with strands of lights, tinsel and glittering ornaments are pulled from the corner of the attic or the back of the closet. Downtown Pensacola will soon be lit up with holiday flare as members of the community come together for one of the city’s favorite annual holiday events: Winterfest.

Winterfest will take over the downtown streets through December 24, featuring new festivities, fan-favorite events and more zany activities. This year’s Winterfest festivities kick off at 223 S Palafox Place in downtown Pensacola. With more actors, songs, festivities and tours, event organizers say this Winterfest is the biggest year yet.

Winterfest’s history originates back to when community members would decorate Pensacola’s downtown historic village and people would drive their cars around to see the lights. From there, a group of neighbors came together to give trolley tours around the village. Soon, they added storylines that took guests through many different classic Christmas stories.

This year, Winterfest has many exciting events in the works such as a couple parades and a brandnew tour. The Elf Parade—which Winterfest puts on every year—gets all the favorite holiday characters together to walk through downtown Pensacola, wave to all the kids and lead to the way to the Christmas market. The market will be held at the plaza at the corner of Zaragoza and Tarragona Streets.

The beloved Grinchmas parade encourages folks to bring the Grinch presents that would make his heart grow three sizes. Eventgoers may bring things like onions, drawings of the Grinch, shiny things to bring to Martha May Whovier and tools to work on his trolley with.

“Everyone who’s anyone in Whoville will be there—a real Who’s Who, if you will,” Winterfest PR Manager Kismet Dunkerly said. Dunkerly has worked with Winterfest since 2019, and in 2021, Dunkerly started to work in Winterfest’s public relations department.

Also coming this year is the brand-new trolley tour “A Whoville Christmas Caper,” which will take guests on a 25-minute ride to see the beautiful holiday decorations around downtown Pensacola. While Winterfest organizers warn that the Grinch is on some sort of a decoration-stealing bender, they assure guests that he will not spoil any of the fun.

“I’m beyond excited for this tour because we’ve cast the most wonderfully hilarious and talented Whos we could find, and they do not disappoint,” Dunkerly said.

Finally, Winterfest will be hosting the talented artist, Mr. Scott, who will transform guests into caricature Whoville versions of themselves. Mr. Scott has been a professional artist for more than 35 years. He is proficient in a variety of different styles, but he is best known for his comic book art style. You can check out some of Mr. Scott’s artwork online at

To be sure you do not miss out on any of the Winterfest fun, we have brought you complete details on this year’s holiday tours, performances, photo opportunities and more. For tickets and to view the full lineup of scheduled Winterfest events, visit

A Whoville Christmas Caper

In this brand-new trolley tour, the Grinch is back to his old tricks, but the Whoville police are hard at work to be a match for his mischief-making pranks. Winter fest organizers advise the Pensacola community to guard their Christmas trees and cheer, for the Grinch is on the loose. Cindy Lou Who may be able to save the day and melt the Grinch’s hard, cold heart—or the Grinch will end up in the Whoville slammer. Either way, join the Whoville gang for an evening of excitement as the hunt is on for that naughty Grinch. Tickets are $10 for children and $14 for adults.

The Grinch’s Merry Match

A fan-favorite trolley tour that debuted in 2021, the Merry Match, is back again this year. The Grinch was getting a little jealous of everyone else having a trolley tour but him, so he decided to build his own trolley from trash he found on Mount Crumpit. Winterfest organizers hope the trolley will hold together but assure guests that the Whoville fire department is always ready with their emergency exit slide in case anything goes wrong. Tickets are $10 for children and $14 for adults.

Scrooge Tour

Take part in some ghostly fun with the classic tale: A Christmas Carol. Beginning at the steps of the old courthouse for a free to the public pre-show, guests will encounter Ebenezer Scrooge’s long-deceased partner Jacob Marley. Marley wears many chains around him with each link representing a selfish misdeed from his life. During the 25-minute trolley tour, guests will meet the Ghosts of Christmas Past, Present and Future as they show Scrooge how he became so callous toward others, what the true meaning of Christmas is and that fortune is not as important as he thought. Tickets are $16 for children and $20 for adults.

Polar Express Tour

Join the Conductor for a magical journey through a wormhole on the Polar Express. Share in the adventure as the Conductor recounts the story of the boy who received the first gift of Christmas: a bell from Santa’s sleigh. Rekindle the wonder of the beloved storybook, along with the belief in the magic of Christmas. Remember to dress warm and cozy for this open-air trolley ride. Tickets are $9 for children and $12 for adults.

Tombstone Photos with the Ghost of Christmas Future

After the Scrooge tour, guests may encounter the Ghost of Christmas Future and get a photo taken with their own tombstone including a personalized epitaph. There will be 10 styles of epitaphs to choose from. Just fill in the names of the party and pick the epitaph for each person after booking tickets. Additional charges may apply.

Photos with Santa

Santa Claus is coming to town and will be available for pictures after each trolley tour. Professional photos will be available for purchase and guests are welcome to bring their personal cameras to take pictures or video during their visit. Children can also bring their Christmas letters to give to the jolly man himself, or they can drop them off in mailboxes that will be stationed throughout the event space. Digital files cost $37 to $50. If you have a large group and would like to take lots of photos, make sure to reserve extra time.

Photos with the Grinch

Mr. Grinch sure is a mean one, but Santa’s favorite nemesis is begrudgingly allowing Winterfest guests to invade his space for this viral photo opportunity. Guests will meet the Grinch at his throne behind Santa’s sleigh, but unlike Santa, the Grinch likes to ask children what they do not want for Christmas. Guests should take caution, though, as Mr. Grinch has some tricks up his sleeve and a special lever that can launch guests out of their seats. Digital files cost $37 to $50. If you have a large group and would like to take lots of photos, make sure to reserve extra time.