Calendar – Jolley Trolley
Nov
30
Sat
Wine Walk @ Sponge Docks
Nov 30 @ 5:00 pm – 9:00 pm
Dec
6
Fri
There’s Snow Place Like Tarpon Springs @ Downtown Tarpon Springs
Dec 6 @ 5:00 pm – 10:00 pm
Dec
7
Sat
Macy’s Miracle on Cleveland St. @ Cleveland St
Dec 7 @ 8:00 am
Macy's Miracle on Cleveland St. @ Cleveland St

This free holiday festival returns for the 13th year when the 400-600 blocks of downtown Clearwater’s Cleveland Street District will be transformed into a holiday wonderland complete with falling snow, an ice skating rink, Holiday Express Train, and pictures with Santa ($5 per photo). Mayor George Cretekos will kick off the event by lighting the tree at Station Square Park. Festivities will also include face painting, inflatable bounce houses, a scavenger hunt with the chance to win tickets to shows, Chick Fil A giveaways, and brand new children’s bicycles, courtesy of Baystar Restaurant Group. The following activities require a wristband, which can be purchased for $8: Holiday Express Train, ice skating, inflatable bounce houses, Rock em Sock em Robots. The festival will feature vendors with arts and crafts and holiday themed-food and refreshments available for purchase throughout Cleveland Street.

Dec
8
Sun
Santa & Suds 5K Run (Walk) & Fun Street Party @ Clearwater
Dec 8 @ 4:00 pm
Dec
14
Sat
31st Annual Say No To Drugs Holiday Classic @ Downtown Clearwater
Dec 14 @ 7:00 am – 2:00 pm
Christmas on the Sponge Docks @ Tarpon Springs Sponge Docks
Dec 14 @ 2:00 pm – 8:00 pm
Old Fashioned Christmas & Holiday Parade @ Downtown Dunedin
Dec 14 @ 4:00 pm – 9:00 pm
Dec
22
Sun
The Downtown Dunedin Christmas Half Marathon With 10K 5K And Toy Drive @ Downtown Dunedin
Dec 22 @ 6:45 am – 12:00 pm