Our favorite holiday things to do downtown

Posted: Nov 30, 2021 02:58 pm Updated: Oct 17, 2023 09:02 am

For two months beginning in mid-November, visitors to downtown Pensacola can experience music, shopping, food, art and nightlife under a canopy of four hundred thousand white lights illuminating historic buildings, parks, shops, galleries and outdoor spaces. You can navigate the eclectic district that’s anchored by Palafox Street—named one of America’s “Ten Great Streets”—on foot, bicycle, Segway® or even horse and carriage

The iconic Winterfest offers families unique opportunities to enjoy interactive outdoor entertainment based around holiday themes like the Polar Express, A Cajun Christmas, The Grinch and more. Winterfest 2021 events are set for Nov. 21, 26, 27, and 28; December 3, 4, 10, 17, 18, 19, 21,22, 23 and 24. To purchase tickets to tours or photos with Santa or the Grinch, click here

While you are visiting Downtown Pensacola, don’t forget about the outstanding local shops and boutiques. Not only do downtown shops like Don Alans and The Market and Mainly Shoes offer some of the most exclusive and trendy merch around, but one lucky downtown shopper will win a $1,000.00 Visa gift card to enjoy yet more of that that great holiday bounty.

The “All I Want” giveaway, sponsored by Pensacola’s Downtown Improvement Board, awards shoppers one chance to win the gift card for every $10 they spend.  And that’s not just merchandise purchases, but also food and drink, as well.


All you have to do is upload your receipts here. The contest winner will be announced on Christmas Eve. 


If you happen to be in town on any of the following dates, you could head to Downtown Pensacola for some live Christmas spirit.


·      Pensacola Symphony presents: “Home for the Holidays Featuring Ashley Brown,” on 28 November at the Saenger Theatre.

·      StoryTyme with Grandma Jenkins, presented by University of West Florida Historic Trust, will have holiday themes on Dec. 3 and Dec. 17, at the Pensacola Children's Museum.

·      K-LOVE Christmas, Dec. 4, at the Pensacola Bay Center.

·      Pensacola Children’s Chorus presents, “Christmas on the Coast,” on Dec. 10-12, at the Saenger Theatre.

·      “1940’s Radio Hour,” on Dec. 10-19, at the Pensacola Little Theatre

·      White Tie Christmas, on Dec. 18, at the Pensacola Bay Center.

·      Ballet Pensacola presents “The Nutcracker,” on Dec, 17-19 at the Saenger Theatre.