Holiday Extravaganza

Festive Holiday Fun in Downtown Clearwater

Holiday Season Memories

Recap video of our 2021 Holiday Extravaganza in Downtown Clearwater.

2021 Holiday Season Programming and Events


The Market Elaine Holiday Market – December 16
Introducing The Market Elaine, the spunky nighttime sister to Clearwater’s already popular The Market Marie, taking place outside of Station Square Park from 5 pm – 9 pm featuring a mix of 50+ local vendors and artisans from across the Tampa Bay Area perfect for holiday gift giving season.

The Market Marie – December 11
The second Saturday each month from 9 am – 2 pm at the corner of Court and Myrtle. Join over 85+ local farmers and artisan vendors.

Clearwater Hispanic Farmers Market – December 18 and 19
The third weekend of the month, on both Saturday and Sunday from 9 am – 3 pm the Clearwater Hispanic Farmers invites you to the corner of Court and Myrtle for a unique market infused with Hispanic flare.


Thursday Night Holiday Movie Series – December 9, 16, 23, 30
Watch a holiday movie favorite at the historic Nancy and David Bilheimer Capitol Theatre.
Showtime at 7:30 pm. Free admission.

–   December 9 – National Lampoon’s Christmas Vacation
–   December 16 – Die Hard
–   December 23 – The Muppet Christmas Carol
–   December 30 – Last Holiday

Monday Night Holiday Movie Series – December 13, 20
Watch a holiday movie favorite at the historic Nancy and David Bilheimer Capitol Theatre.
Showtime at 7:00 pm. Free admission.
Presented by 12 Days of Christmas Clearwater.

–   December 13 – Elf  |  VIP seating for First Responder Families
–   December 20 – Prancer  |  VIP seating for Military Families

Movie Matinee and Breakfast with Santa – December 18 and 19
Wake up this weekend to enjoy free breakfast with Santa from 9 am – 11 am on the 400 block of Cleveland Street before seeing holiday animated favorites at the historic Nancy and David Bilheimer Capitol Theatre.
Breakfast sponsored by 12 Days of Christmas Clearwater.
Showtime at 11:30 am. Free movie admission.

–   December 18 – The Grinch (2018 Animated Movie)
–   December 19 – The Polar Express

The Nancy and David Bilheimer Capitol Theatre is located at 405 Cleveland Street.


Clearwater Holiday Pet PAW-rade – December 18
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 and The Grinch. Enjoy music, pet treats, pet costume contests, and more family fun. Registration starts at Noon.

Parade Route: 400 – 600 blocks of Cleveland Street in Downtown Clearwater
12 pm – Registration
1 pm – Parade Kicks Off

Costume Contest Categories
– Best Dressed Dog (awarded for small, medium, and large dogs)
– Best Dressed Cat
– Best Dressed Critter (Non-dog or cat)
– Best in Show Pet (outfit plus accessories, vehicle, float, wagon, stroller, bike, etc.)
– Most Festive Pairing (Pet + Human/s)
– Fan Favorite – VOTE for your favorite

>>> View Parade Photos and Photos with Santa Here <<<

Benefiting SPCA Tampa Bay – Suggested donation to enter the costume contest.
Free to march in the parade.

Presented by the Downtown Clearwater Merchants Association. In partnership with 12 Days of Christmas Clearwater and the City of Clearwater Community Redevelopment Agency.

Kids and Family

Winter Wonderland
Clearwater Community Volunteers presents Winter Wonderland, a charity drive benefiting the children of Pinellas County. Winter Wonderland is a complete Christmas village with entertainment, photos with Santa, cookie decorating with Mrs. Claus, a hot chocolate shop, a petting zoo, pony rides, playground, a Bouncy House, a Giant Slide and the Holiday Express Train!

The Hispanic Holiday Event – December 9
Enjoy a family friendly Christmas celebration featuring Dinner with Santa complete with food, games, crafts, movies, and music in Station Square Park beginning at 4 pm. Plus a Christmas Jewelry Fair. Presented by the Hispanic Outreach Center.

The 12 Days of Christmas – December 12-23
Opening Celebration – December 12 

Kick off the 12 Days and celebrate in Station Square Park with the reading of a classic holiday story from Mrs. Claus. Plus, an appearance from The Grinch and Cindy Lou Who at 6 pm.

Each of the 12 Days of Christmas in Clearwater through December 23 offers something fun and different to do.

Breakfast with Santa/Desayuno con Santa – December 19
Enjoy breakfast with Santa at this free community event presented by Clearwater Legal Center/Centro Legal de Aguas Claras at 1235 Cleveland Street from 11 am – 1 pm.


Window Displays
Located across downtown check out colorful and artistic window displays inspired by the holiday season. List of Window Display Locations.

See highlights from last years 2020 Holiday Extravaganza window displays.


America’s Everglades – Through the Lens of Clyde Butcher
Experience the natural beauty and boldness of Clyde Butcher’s monumental black and white photography in a museum-quality art gallery inside the Clearwater Public Library. This exhibit features an accumulation of images from Clyde’s beloved Everglades on display now through May 2022. Free admission.

Public Art Walk – December 18
Every third Saturday, join the Clearwater Arts Alliance on a leisurely stroll past some of Downtown Clearwater’s amazing public art.

Food and Spirits

Dine Out for a Difference – December 16
Each month, the restaurants in The District donate 10% on one night to a local charity: 11 restaurants / 1 night / 1 cause. This month join us in supporting SPCA Tampa Bay.
Presented by Downtown Clearwater Merchants Association.

Sip and Stroll – December 18
The District invites you to sip and taste from 10+ local restaurants strolling the 400 – 500 blocks of Cleveland Street. Featuring outdoor entertainment and festive holiday décor.
Presented by Downtown Clearwater Merchants Association.

Dancin’ in The District: Kickin’ 2021 to the Curb New Year’s Eve Party – December 31
Countdown to midnight and enjoy a night of music and dancing on Cleveland Street.
Presented by Downtown Clearwater Merchants Association.


Clearwater Jazz Holiday presents Wanderlust – Nov. 27 and Dec. 4, 11, 18
Bistro inspired outdoor concert series Saturday nights at 6 pm in Station Square Park. Tickets available now.

–   November 27 – Alex Harris and Songbird Shella & Friends
–   December 4 – Fusik and Pockit
–   December 11 – A special eveving with Love Alive: A Tribute to Heart – 2 sets
–   December 18 – Jazmin Ghent and Giants of Jazz, a Young Lions Showcase

Peace Concert Series presents Holiday Magic – December 12
To awaken your holiday mood, our December program will feature the beautiful voices of the Qol Quartet. Their selections will include Christmas favorites, works from Handel’s Messiah and carols for all to join is the singing. No tickets needed but an offering will be taken ($5-$10 minimum suggested). Doors open at 2:30 pm. Showtime at 3 pm. Peace Memorial is located at 110 S. Fort Harrison Avenue.

Holiday Voucher Program

Available December 1 – 31, 2021. Redeem your Holiday Voucher at participating Downtown Clearwater retailers, restaurants, cafes, and bars to enjoy $10 OFF your bill, with a minimum purchase of $15. While supplies last. Limit one per customer.


Parking in Downtown
Enjoy free parking on weekends and after 6 pm on weekdays at designated locations.

Holiday Fun Beyond Downtown

Making Spirits Bright Parade presented by The 12 Days of Christmas Clearwater Beach – December 14
Local businesses and residents alike are welcome to participate in this festive parade that will travel from Island Way Grill to North Beach and South Beach. Parade line up begins at 3:30 pm.

Stroll of Trees presented by The 12 Days of Christmas Clearwater Beach – December 21-24
Visit participating local businesses to view themed Christmas Trees. Collect a sticker for each tree you visit. If you visit them all you will be entered to win a weekend stay at our hotel sponsor!

Light it up Clearwater! Fireworks – December 31
Clearwater Beach’s Annual Fireworks New Year’s Eve Celebration at midnight. Presented by AMPLIFY Clearwater.

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