Holiday Extravaganza

Festive Holiday Fun in Downtown Clearwater



Celebrate the holidays in Downtown Clearwater with lights, decorations, music, merriment, and festive holiday events all season long.

Watch highlight video from the 2021 Holiday Extravaganza.


City of Clearwater Tree Lighting Ceremony 

Wednesday, November 30th from 6:00 pm – 8:30 pm | FREE
Station Square Park | RSVP on Facebook

Celebrate the start of the holiday season by lighting up Clearwater’s Christmas Tree with Santa and all his holiday friends during a special night filled with holiday cheer, festive games, giveaways, vendors, music, and real snow! 

Special holiday performances by St. Cecelia’s Church Children Choir, Sacred Heart School Choir, YMCA of the Suncoast Dance Academy, and more.

Presented by:  City of Clearwater, Clearwater Downtown Development Board, and Clearwater Community Redevelopment Agency 

Watch 2021 Tree Lighting Ceremony Video

Clearwater Jazz Holiday Wanderlust Concert Series 

Saturdays – Nov. 26 and Dec. 3, 10, 17
Doors open at 5:30 pm  |  Performance 6:00 pm – 9:00 pm
Station Square Park

Bistro inspired outdoor concert series Saturday nights in Station Square Park. Tickets available at:

Saturday, November 26

  • 6:00 pm – 7:15 pm Tommy Shugart Organ Trio featuring Eddie Roberts
  • 7:30 pm – 9:00 pm Eddie Roberts & Lamar Williams Jr of The New Mastersounds with Tommy Shugart, Matt Lapham, Taylor Galbraith and Solomon Keim

Saturday, December 3

  • 6:00 pm – 7:15 pm The HeadTones
  • 7:30 pm – 9:00 pm Grindstone Sinners

Saturday, December 10

  • 6:00 pm – 7:00 pm Arts Conservatory for Teens Holiday Tour Hosted by Alex Harris
  • 7:30 pm – 9:00 pm The Alex Harris Band

Saturday, December 17

  • 6:00 pm – 7:15 pm CJH Giants of Jazz Annual Young Lions Show Hosted by Frank Williams
  • 7:30 pm – 9:00 pm Kat Riggins & her Blues Revival

Presented by:  Clearwater Jazz Holiday 

Miracle on Cleveland Street 

Sunday, Dec. 4 from 2:00 pm – 6:00 pm | FREE
Cleveland Street at Osceola Avenue | RSVP on Facebook

Ruth Eckerd Hall On The Road Presents Miracle on Cleveland Street in Downtown Clearwater. This FREE family-friendly festival returns for the 14th year when the 400 block of Cleveland Street will be transformed into a holiday wonderland with falling snow, a variety of live music including strolling carolers, holiday themed selfie-photo stations and activities that include:

  • A photo and meet and greet opportunity with the big-guy himself, Santa Claus!
  • The always-popular Tel-An-Elf where children can call the North Pole to video chat with Santa’s Elves.
  • Hop on board the Holly Jolley Trolley and enjoy a holiday sing-a-long ride through downtown Clearwater.
  • The thrilling Xtreme Board Snowboard Simulator! Thrill-seekers of all ages step on a snowboard simulator for a half-pipe design ride surrounded by a mountain backdrop that feels like the real thing!
  • Ice skating Florida style on a synthetic ice rink!
  • Gingerbread Mini Putt-Putt Golf for kids. Children can work on their swing and go for the hole-in-one, using kid-friendly equipment!
  • An Ornament Craft Station where children can create and take home their very own holiday tree ornament!
  • Touch-A-Truck Emergency Vehicles on site for up-close inspections!

Children can participate playing FREE games for prizes, such as:

  • The Snowball Toss Game is the classic ping-pong tossed into little snowman themed jars for a chance to win a prize!
  • The Lollipop Tree will have lollipops on it and kids can grab a lollipop to win a prize!
  • Embark on a holiday-themed Scavenger Hunt throughout the festival with a chance to win a new bicycle!

Holiday themed-food and refreshments will be available for purchase at the Nancy and David Bilheimer Capitol Theatre. A community holiday concert performed by the Ruth Eckerd Hall Chorus featuring the Salvation Army Music and Arts Ensembles will be the finale of the day’s activities beginning at 6 pm in the Bilheimer Capitol Theatre.

Presented by:  Ruth Eckerd Hall 

Food Truck Thursdays Holiday Jingle

Thursday, Dec. 8 from 11:30 am – 2:00 pm 
Station Square Park | RSVP on Facebook

Enjoy your lunch break outside in festive Station Square Park with music, games, two food trucks, dessert, and more holiday surprises.  

Presented by: KnowBe4

Cocktails and Candy Canes    

Thursday, Dec. 8 from 5:00 pm – 7:30 pm 
Cleveland Street and Fort Harrison Avenue  

Registration. Presented by:  Amplify Clearwater

Holiday Spirit of Lights Festival in Downtown Clearwater  

Friday, Dec. 9 from 6:00 pm – 10:00 pm | FREE
Cleveland Street from Osceola Avenue to East Avenue | RSVP on Facebook

Stroll Downtown Clearwater’s holiday lights and experience an extra special night of holiday festivities with free family activities including glow in the dark putt-putt mini golf, train rides, bounce houses, crafts, face painting, Kona Ice, and special holiday picture opportunities.

Enjoy festive carolers, bands, live music, stilt walkers, The Grinch, Elsa, Ana, Olaf, reindeers, and Santa.  

Presented by:  City of Clearwater, Clearwater Downtown Development Board, and Clearwater Community Redevelopment Agency 

Help us stuff a trolley for Kimberly Home by donating items such as:
Diaper bags, diaper creams, baby wipes, paper towels, baby bath towels, wash clothes, washcloths, baby pajamas, onesies, socks, crib sheets, baby blankets, baby accessories, twin bed sets, pillows, books, baby toys, toddler toys, or gift cards

The Market Marie on Cleveland Street 

Saturday, Dec. 10 from 10:00 am – 2:00 pm | FREE | RSVP on Facebook

Cleveland Street from Osceola Avenue to East Avenue and Station Square Park 

Outdoor farmers and artisan market featuring unique mix of 100 + local vendors along Cleveland Street on the 2nd Saturday monthly with entertainment and an extra touch of holiday flare with a visit from Santa Claus. 

Holiday Trivia Night at Downtown Pizza     

Wednesday, Dec. 14 and Wednesday, Dec. 21 at 7:00 pm 

Downtown Pizza at 428 Cleveland Street  

Think you know everything about the holidays? Test your holiday knowledge and get in the holiday spirit at trivia night while enjoying everyone’s favorite traditional holiday treat…pizza!  

Dinner with Santa      

Friday, Dec. 16 from 5:00 pm – 8:30 pm | FREE
Station Square Park

Enjoy a family friendly Christmas celebration featuring Dinner with Santa complete with food, games, crafts, movies, music and a Christmas Jewelry Fair. 

Presented by: The Hispanic Outreach Center 

Yuletide Magic      

Wednesday, Dec. 21 at 6:30pm | FREE
Station Square Park | RSVP on Facebook

Premier Dance will be presenting holiday themed and dance performances in all different genres including ballet, jazz, lyrical, pom, salsa and ballroom with dancers ages 3 and up!

Holiday Performances at the Bilheimer Capitol Theatre       

The Nancy and David Bilheimer Capitol Theatre, a cultural landmark in Downtown Clearwater, presents the following festive performances this holiday season:

405 Cleveland Street | Tickets

And More… 

Check out our full calendar below for even more events.

View Holiday Highlights Flyer PDF

Holiday Stroll

Every night in December from 6:00 pm – 10:00 pm | FREE

Cleveland Street from Osceola Avenue to East Avenue and Station Square Park  

‘Tis the season to bring families together in Downtown Clearwater for a magical, holiday stroll of lights each night over the holiday season. On select evenings enjoy FREE pop-up special performances in Station Square Park to get you in the holiday mood.

Special Pop Up Holiday Performances | FREE

Select dates in Station Square Park | RSVP on Facebook 

  • Dec. 13 – MZ Dance Studio | 7:00 pm
  • Dec. 14 – Frozen Stories in the Park | 4:30 pm
  • Dec. 14 – Clearwater Band | 6:30pm
  • Dec. 15 – Plumb Elementary Chorus | 6:30pm

Pet Parade

The 2nd Annual Home for the Holidays Paws-on-Parade

Saturday, Dec. 17
Parade kicks off at Cleveland Street and Fort Harrison Avenue at 11:00 am
Festival 12:00 pm – 2:00 pm 

Cleveland Street from Fort Harrison Avenue to Station Square Park

2022 Registration Coming Soon 

Suggested donation benefiting the Humane Society of Pinellas to enter the costume content.

Costume Contest Categories:

  • Best Dressed (small, medium, and large)
  • Best in Show Pet
  • Most Festive Pairing (Pet and Humans judged together)
  • Fan Favorite

FREE to march in the parade.

Bring your furry loved ones to wag, woof and celebrate the holidays down Cleveland Street during this pet friendly parade. Dress in your holiday finest for pet and family photos with Santa. Who will win best dressed pet? Check out the pet vendor market, meet local rescue groups, and pet adoptions. Plus, treats, music, and more holiday spirited fun for all.  

RSVP on Facebook

Presented by: Clearwater Downtown Development Board, Clearwater Community Redevelopment Agency, the City of Clearwater, Humane Society of Pinellas, and Tiny Paws. 

Watch 2021 Parade Highlights Video and view 2021 Parade Photos and Pet Photos with Santa



Window Displays

Located across downtown check out colorful and artistic window displays inspired by the holiday season.

Participating 2022 locations coming soon.

Watch highlights from 2021 and 2020.

Station Square Park 

The heart of the holiday season in Downtown Clearwater is Station Square Park at 612 Cleveland Street featuring the City of Clearwater’s Christmas Tree, lights, decorations, and is the home to many of our special events and performances.


What the Holidays Mean to You? Coloring Contest  

Dec. 1 – 23 
Clearwater Public Library Main Branch

Kids 10 and under, are invited to help make the Library, festive this holiday season.  Beginning on Dec. 1st, pick up your wood ornament at the Main Library.  Show us through your art “What the Holidays Mean to you?” Contest ends on Dec 23rd.  

Elf on the Shelf invades Downtown Clearwater 

Dec. 1 – 24

Watch daily videos at

Holiday Solar System Neighbors Program   

Thursday, Dec. 1 from 5:30 pm – 7:00 pm | FREE
Clearwater Public Library Main Library

Join us in front of the library with our very own NASA ambassador and the Clearwater Sister Cities to enjoy the incredible views of the Moon, Jupiter, and Saturn through the lens of a telescope! Did you know Clearwater’s Sister City is Nagano, Japan? Otsukimi or “moon-viewing” is a festival in Japan honoring the moon. Bring the whole family to the library and learn origami, take pictures with our green screen and enjoy some hot cocoa and candy canes to make the night complete. All ages welcome. Weather permitting.

Winter Wonderland 

Select nights Dec. 3 – 23 from 6:00 pm – 9:00 pm
Fort Harrison Avenue and Drew Street

Each year since 1993, the Clearwater Community Volunteers put on Winter Wonderland, which is a charity drive in downtown Clearwater whose proceeds benefit the children of Pinellas County. Winter Wonderland is a complete Christmas village with an entertainment stage, photos with Santa, cookie decorating with Mrs. Claus, a hot chocolate shop, and Holiday Express Train!

Entrance to Winter Wonderland is free but we ask visitors to bring a non-perishable food item and/or an unwrapped toy. The toys and canned goods are donated to local area charities, such as the Homeless Emergency Project sponsored by Everybody’s Tabernacle.

Winter Wonderland is open from 6:00 pm to 9:00 pm, Wednesdays through Sundays. Grand Opening on Saturday, December 3rd and Closing Night, Friday, December 23rd. Winter Wonderland is closed the first two weeks Monday and Tuesday but open the 3rd week all week! Click Here for additional details on this year’s Winter Wonderland.

The Elves & the Shoemaker 

Dec. 17 from 2:00 – 3:00 pm | FREE
Clearwater Public Library Main Branch

The Atlantic Coast Theatre for Youth presents “The Elves & the Shoemaker” at the Clearwater Public Library. The classic Brothers Grimm story takes the stage as an original musical with new lyrics set to traditional holiday melodies. An Elf must help a poor shoemaker… with the help of the elves in the audience.


Free and convenient parking can easily be found throughout Downtown Clearwater. Please read all posted signage prior to parking.

>>> Click Here to learn more about available parking options.


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Clearwater Jazz Holiday Wanderlust Concert Series


City of Clearwater Tree Lighting Ceremony

Holiday Solar System Neighbors Program


Clearwater Jazz Holiday Wanderlust Concert Series

Grand Opening of Winter Wonderland Clearwater

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