Calendar – Jolley Trolley
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.

Honeymoon Island Bluegrass Festival @ Honeymoon Island
Dec 7 @ 11:00 am – 5:00 pm
Holiday Boat Parade & Tree Lighting @ Edgewater
Dec 7 @ 6:00 pm – 9:00 pm
Dec
8
Sun
HOB Vegan Food Truck Rally @ HOB Brewing Company
Dec 8 @ 12:00 pm – 6:00 pm
Dec
14
Sat
Tarpon Springs Christmas Parade @ Downtown Tarpon Springs
Dec 14 @ 10:00 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
Island Estates Boat Parade and The Florida Brass Alumni Drum And Bugle Corps @ Coachman Park
Dec 14 @ 8:00 pm
Dec
21
Sat
Annual Holiday Parade @ Downtown Palm Harbor
Dec 21 @ 3:00 pm
Dec
31
Tue
NYE Fireworks Celebration @ Clearwater Beach
Dec 31 2019 @ 4:00 pm – Jan 1 2020 @ 7:00 pm