Do The Ugly Sweater Pub Crawl in Pensacola

Schedule

Sat Dec 13 2025 at 04:30 pm to 09:00 pm

UTC-06:00

Location

The Kennedy | Pensacola, FL

Advertisement
Do The Ugly Sweater Pub Crawl! 25% OFF code: UGLY25 good until November 22nd! Get your tickets NOW before they are all sold out!
About this Event

Do The Ugly Sweater Pub Crawl is coming to Downtown Pensacola - so grab your gaudiest holiday gear and get ready to sleigh! Whether you sparkle, jingle, or light up like a Christmas tree, this is your time to shine. It’s Escambia County's most wonderfully tacky tradition, where the only rule is: the uglier the sweater, the better the night.

With games, contests, prizes, and downtown holiday cheer, this is the Ugly Sweater Pub Crawl event you won’t want to miss. Come solo, bring your holiday honey, or roll deep with your elf squad—it’s going to be one festive night to remember!

What to expect at your Do The Ugly Sweater Pub Crawl:

Express Check-in: Skip the line and check yourself in when you arrive—no waiting, no hassle, just pure peppermint-powered fun. Your night of holiday cheer starts whenever you do! (Note: This check-in is for the event entrance, not individual pub crawl recommended stops.)

Social Media Challenges:

SAY CHEERS! Largest Group Pic on the ‘gram
Snap and post a fabulously festive group photo with your sweater-clad squad (or anyone rocking holiday spirit) for a chance to win SAY CHEERS!

SHOW US YOUR SIPS! Post a Festive Beverage Pic on the ‘gram
Got a cozy creation in a holiday mug or a cup of cheer that makes your sweater shine even brighter? Post it—yes, even if it’s just hot cocoa or sparkling cider. We see you.

Best Dressed Contest: Drop your pic on Facebook
Don your most ridiculous, bedazzled, or LED-lit holiday sweater. The uglier, the better. Post, tag, and you could end up sleighing the prize game!

Trivia on X: Head over to X (formerly Twitter), answer a quick holiday-themed question, and you might be picked to win a little extra joy.

Digital Photo Frames: Capture all your merry moments with our Ugly Sweater-themed digital photo frames—perfect for spreading joy (and envy) on the 'gram!

Geo Charms: Unlock geo-located charms as you crawl—collect them all for a chance at prizes that’ll make you feel like the star on top of the tree.

A variety of atmospheres at the different Pub Crawl recommended stops!
Every spot brings a little something different—cozy, quirky, classy, or chaotic. You never know which kind of holiday magic you’ll find!

*** Tickets are available exclusively through Eventbrite, or our website! ***

No tickets sold at the door!
https://dothecrawl.com/Pensacola/Ugly-Sweater

Experience a new, low-contact, express check-in adventure.
(Note: This check-in is for the event entrance, not individual pub crawl recommended stops.)

To fully enjoy Do The Ugly Sweater Pub Crawl:

Dress to Impress (or Distress) in Your Ugliest Sweater – We're talkin’ pom-poms, jingle bells, tinsel, lights, and anything fabulously festive or hilariously hideous!

Enter our Best Dressed Contest by posting your holiday sweater photo on Facebook—sassy Santas, festive freaks, and all things cheerfully chaotic welcome!

Enjoy quick and easy express check-in – no waiting, just step into the holly-jolly madness and start the fun.
(Note: This check-in is for the event entrance, not individual pub crawl recommended stops.)

Join in our festive activities:
Snap & post your biggest group photo on Instagram for our SAY CHEERS! contest
Show off your most fabulous festive sip on Instagram for SHOW US YOUR SIPS!
Answer a quick holiday-themed trivia question on X (formerly Twitter) for a chance to win!

Collect geo-charms at pub crawl recommended stops for more chances to sleigh the prize game!

A mobile device with internet access is a must at the event to:
• Access maps and schedules
• Use the digital photo frames
• Join in on social media contests (Facebook, Instagram, and X)
• Collect Digital Geo Charms
• Access your Digital Wristband
• Win prizes!

Do The Crawl Has Revolutionized the Pub Crawl Experience!
We’re all about the laughs, the outfits, and the memories. Come for the vibe, stay for the crew. It’s not about the chug, it’s about the cheer.

Join us for a unique and delightfully tacky holiday pub crawl that stands out from the rest. Here's what makes Do The Ugly Sweater Pub Crawl unlike any other:

  1. Best Dressed Contest
    Share a photo of your most outrageous holiday sweater on Facebook during the event to enter! You must participate in the contests and be present for your chance to win.
  2. Express Check-In, Anytime from 4–9 PM
    Start when you're ready! Check in at any pub crawl recommended stop between 4 PM and 9 PM. We recommend arriving by 5 PM to get the most festive fun in!
    (Note: This check-in is for the event entrance, not individual pub crawl recommended stops.)
  3. Engaging Activities
    No waiting around—our Express Check-In gets you right into the holiday fun with contests, games, and prize opportunities.
  4. Your Smartphone, Your Sleigh Ride
    Keep everything handy with your phone! Access maps, schedules, and contests—all from your device while you crawl.
  5. Social Media Shenanigans
    Snap, post, and win! Join our social media contests on Facebook, Instagram, and X to stay connected and possibly score some merry little prizes.
  6. Self-Guided with a Festive Flow
    Our crawl is self-guided, but following your schedule helps keep the energy high and the fun shared with fellow sweater-wearing legends.
  7. Festive Finds at Every Stop
    As you mingle and make merry, you’ll discover a variety of options at each pub crawl recommended stop.
    (Note: Drinks are purchased separately. Any food or drink specials are at the sole discretion of the pub crawl recommended stops and are subject to availability.)

This isn’t just a pub crawl—it’s an interactive experience.
We’ve reimagined the traditional crawl to celebrate what really matters: festive fun, outrageous sweaters, and holiday cheer with friends. Get ready for a night of merry mayhem, joyful photo ops, and chances to win holly-jolly prizes—because this pub crawl is snow much fun and totally un-sweater-gettable!

You must be 21 years of age or over to participate.
Always have a sober driver and enjoy the crawl responsibly.
For full event details, visit:
https://dothecrawl.com/Pensacola/Ugly-Sweater

Be sure to read our FAQ!
https://dothecrawl.com/FAQ

*Note: All drink and food specials are solely at the discretion of the pub crawl recommended stops and are subject to availability. Specials may be offered during event hours but are not guaranteed and are not included with your ticket.

†Mobile device with internet access required (data rates may apply). Charge up your device and consider bringing a battery backup, to make sure you don’t miss out on all the fun!

‡Prizes are awarded across all participating towns (participating towns listed at dothecrawl.com). Prizes are awarded via the social media platform the contest is played on, and by a valid email address, only. Prizes must be claimed by direct message on the corresponding social media platform within 72 hours of the end of the event. Must attend event to win.

Pub crawl recommended stops are subject to capacity restrictions. Pub crawl recommended stops are subject to change.

Please read our COVID-19 warning here: https://dothecrawl.com/covid-19

For more info about this event in Pensacola, Florida, visit:
https://dothecrawl.com/Pensacola/Ugly-Sweater

Advertisement

Where is it happening?

The Kennedy, 1 Palafox Place, Pensacola, United States

Event Location & Nearby Stays:

Tickets

USD 19.19 to USD 23.77

DoTheCrawl.com

Host or Publisher DoTheCrawl.com

It's more fun with friends. Share with friends

Discover More Events in Pensacola

Sat, 13 Dec at 11:00 am Warhammer 40k Doubles Event

1132 Creighton Rd, Pensacola, FL 32504-7034, United States

Brunch with Santa @Calvert's
Sat, 13 Dec at 11:00 am Brunch with Santa @Calvert's

670 Scenic Hwy, Pensacola, FL, United States, Florida 32503

BRUNCH HOLIDAY
MTG: Avatar the Last Airbender 2HG Event
Sat, 13 Dec at 12:00 pm MTG: Avatar the Last Airbender 2HG Event

2400 West Michigan Avenue Unit 27, Pensacola, FL, United States, Florida 32536

Pensacola SantaCon 2025
Sat, 13 Dec at 01:00 pm Pensacola SantaCon 2025

Pensacola

PARTIES BAR-CRAWLS
The 35th Annual Spirit of Christmas Service - Featuring Granger Smith
Sun, 14 Dec at 10:00 am The 35th Annual Spirit of Christmas Service - Featuring Granger Smith

6205 N W St, Pensacola, FL

CHRISTMAS-SERVICES MUSIC
Santa Paws at Wisteria Tavern
Sun, 14 Dec at 11:00 am Santa Paws at Wisteria Tavern

3808 N 12th Ave, Pensacola, FL 32503-3162, United States

DOG NONPROFIT
Adult & Pediatric CPR\/AED\/First Aid Blended Learning Class
Sun, 14 Dec at 01:00 pm Adult & Pediatric CPR/AED/First Aid Blended Learning Class

Rising Minds Learning

WORKSHOPS VIRTUAL
Sound Bath For Sea Turtles
Sun, 14 Dec at 05:00 pm Sound Bath For Sea Turtles

Parking Lot East Pensacola Beach

HEALTH-WELLNESS MEDITATION
Pensacola Virtual Game Night: Trivia, Charades, and Drawing over Video
Wed, 03 Jun at 07:00 pm Pensacola Virtual Game Night: Trivia, Charades, and Drawing over Video

205 Zaragoza St

ART FINE-ARTS
Dinner Detective Interactive True Crime Dinner Show!
Sat, 02 Sep at 06:00 pm Dinner Detective Interactive True Crime Dinner Show!

8 S 9th Ave

PARTIES ART
Awesome Scavenger Hunt - Pensacola Adventure
Sun, 10 Nov at 08:00 am Awesome Scavenger Hunt - Pensacola Adventure

205 Zaragoza St

ART TRIPS-ADVENTURES
Pensacola Wedding Crashers: Bridal Party Hunt
Wed, 05 Feb at 12:00 pm Pensacola Wedding Crashers: Bridal Party Hunt

221 E Government St

TRIPS-ADVENTURES ENTERTAINMENT
R&B BINGO - 850
Fri, 28 Mar at 07:30 pm R&B BINGO - 850

The Old Piccadilly (Located in back of Town & Country Plaza)

BINGO SPORTS
Singles Party. [Vendors Welcome]
Tue, 01 Jul at 08:00 pm Singles Party. [Vendors Welcome]

Pensacola

PARTIES ENTERTAINMENT
Pop the Balloon Speed Dating.[Vendors Welcome]
Wed, 20 Aug at 08:00 pm Pop the Balloon Speed Dating.[Vendors Welcome]

Pensacola

SINGLES-PARTIES SPEED-DATING
Ghosts of Pensacola: Join the Hunt!
Fri, 05 Sep at 05:00 pm Ghosts of Pensacola: Join the Hunt!

330 S Jefferson St

TRIPS-ADVENTURES CONTESTS
Friday Night Comedy Pacific Kava Downtown Pensacola Hosted By Ryan Pfeiffer
Fri, 12 Sep at 08:00 pm Friday Night Comedy Pacific Kava Downtown Pensacola Hosted By Ryan Pfeiffer

Pacific Kava Bar, West Belmont Street, Pensacola, FL, USA

COMEDY ENTERTAINMENT
Pensacola, FL  Speed Mingle Networking Experience
Tue, 16 Sep at 06:15 pm Pensacola, FL Speed Mingle Networking Experience

Pensacola, FL Speed Mingle Networking Events

SPEED-DATING ENTERTAINMENT
The Ark Encounter and Creation Museum Bus Trip
Mon, 29 Sep at 06:00 am The Ark Encounter and Creation Museum Bus Trip

6205 N W St, Pensacola, FL, United States, Florida 32505

ART PARTIES

What's Happening Next in Pensacola?

Discover Pensacola Events