- November 29, 2022
4TH ANNUAL LIGHT UP OAKLAND/SANTA DAY
3 to 6 p.m. Saturday, Dec. 7, at the Oakland Town Center, North Tubb Street and East Gulley Avenue.
Take the entire family out to the festive event, which offers photos with Santa, Christmas carols with the Oakland Avenue Charter School Choir and special performances from Centre for Dance & the Performing Arts and the Oakland Avenue Charter School Spirit Squad, a DJ, face painting, food trucks and more, culminating in a dazzling town center light-up display at 6 p.m.
10TH ANNUAL JINGLE JOLLY JOG 5K
5 to 8 p.m. Saturday, Dec. 7, at Oakland Park, 15241 E. Oakland Ave., Winter Garden.
Kick off the holiday season with the Jingle Jolly Jog 5K, which starts and finishes within the Oakland Park community. Awards will be presented to the top five overall male and female finishers. There will be a kids’ fun run at 5 p.m., as well. The event features a special visit from Santa, festive activities, complimentary pre-race and post-race food and beverage, a live DJ and much more. The cost is $45 through Dec. 6 and $55 check or cash on race day. The West Orange Junior Service League is the beneficiary.
Registration is available at bit.ly/356ihS2. Wojsl.com.
32ND ANNUAL LIGHT-UP WINTER GARDEN
6 to 9 p.m. Friday, Dec. 6, in downtown Winter Garden.
Sponsored by Duke Energy, the West Orange Ministerial Association and the City of Winter Garden Join us in welcoming the season with this annual event. Enjoy live entertainment, vendors, shopping and children’s activities. Ceremony will begin at 6 pm and the street lighting will take place at 6:15 pm.
39TH ANNUAL OCOEE CHRISTMAS PARADE
10 a.m. Saturday, Dec. 7, starting at the intersection of Maguire Road and Enterprise Street and ending at Bill Breeze Park, 125 N. Lakeshore Drive.
The rain date is 2 p.m. Sunday, Dec. 8. Santa Claus and his helpers will pass out candy and holiday cheer at the annual event, presented by the city of Ocoee and the Ocoee Lions Club.
Judges will score participants in several categories, Youth, Commercial, Non-Commercial and Churches; as well as the Overall Winner.
The grand marshal for the parade will be Dr. Jeffrey Redding, choir director at West Orange High School and artistic and executive director of the Orlando Choral Society.
In lieu of entry fees, parade participants have been asked to take new, unwrapped toys that will be donated to the Ocoee Police Department’s Holiday Toys for Kids in Need. For more than 30 years, parade participants have donated more than 15,000 toys.
For more information, visit ocoeelionsclub.org.
HOLIDAY TREE LIGHTING
5 to 9 p.m. Saturday, Dec. 7, at Ocoee Lakeshore Center, 125 N. Lakeshore Drive.
Enjoy a tree lighting, photos with Santa, a gingerbread house contest, Santa's village, Kid Zone with rides and games, entertainment, arts and crafts and special guests of the city of Ocoee.
(407) 905-3180 or ocoee.org.
OCOEE HOLIDAZE TREE-LIGHTING EVENT
5 to 9 p.m. Saturday, Dec. 7, at the city’s historic Withers-Maguire House, 16 E. Oakland Ave., and the Ocoee Lakeshore Center, 125 N. Lakeshore Drive.
The tree-lighting ceremony will begin at 6:30 p.m. There will be photos with Santa Claus, Santa’s Village, a gingerbread house-decorating contest, Kids Zone with rides, games, entertainment and arts and crafts. The holiday event is open to the public. There will be a small fee for some of the activities.
Santa Claus and Mrs. Claus will meet and greet visitors on the lawn of the Withers-Maguire House from 5:15 to 8:30 p.m. The house, built in 1888, will be decked out in holiday decorations with photo opportunities.
Ocoee Parks and Recreation, (407) 905-3180.
WINTER GARDEN CHRISTMAS PARADE
1 p.m. Saturday, Dec. 7, starting on South Dillard Street, heading north and going west on Plant Street.
This long-standing Winter Garden holiday tradition will delight spectators and ring in holiday cheer. Don’t forget to look for the Big Guy himself at the end of the parade.
Cwgdn.com, (407) 656-4111.