Calendar – Jolley Trolley
Oct
10
Thu
OLL Fall Festival @ Our Lady of Lourdes Catholic Church
Oct 10 – Oct 13 all-day
OLL Fall Festival @ Our Lady of Lourdes Catholic Church

Free Jolley Trolley Shuttle Service.

  • Friday running from 4:30 PM to 11:30 PM from Our Lady of Lourdes fall festival grounds to Dunedin high school parking lot.
  • Saturday running from 4:30 PM to 11:30 PM from OLL Fall Festival grounds to Dunedin high school parking lot.

The shuttle is free and so much fun so make use of it!  It’s your first fair ride of the event.

Nov
30
Sat
Wine Walk @ Sponge Docks
Nov 30 @ 5:00 pm – 9:00 pm
Dec
6
Fri
Dunedin Express @ Dunedin History Museum
Dec 6 @ 4:00 pm – Dec 18 @ 8:30 pm
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
14
Sat
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