Celebrate the holidays in West Orange County

A variety of events are taking place through December to get residents and families in the festive mood for the holidays.


  • West Orange Times & Observer
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Parades, festivals, church events and more are filling up social calendars this December. Find out when and where your favorite holiday event is taking place.

The city of Ocoee is reminding residents that its annual Holiday Tree-Lighting Celebration will not be held this year because of the roadwork and construction near the Withers-Maguire House, where the yearly event is held.

 

WINTER GARDEN

31ST ANNUAL LIGHT UP WINTER GARDEN

6 to 9 p.m. Friday, Nov. 30, on and around Plant Street in downtown Winter Garden. Join Winter Garden as it welcomes the season with live entertainment, vendors, shopping, children’s activities, visits with Santa Claus and more.

The annual event is sponsored by Duke Energy, the West Orange Ministerial Association and the City of Winter Garden.

 

CHRISTMAS PARADE

10 a.m. Saturday, Dec. 1, in historic Winter Garden. The parade starts on South Dillard Street, behind the Wells Fargo bank, and heads north before going west on Plant Street toward City Hall.

This long-standing Winter Garden holiday tradition will ring in holiday cheer with marching bands, performers and myriad decorated floats. Santa and Mrs. Claus will greet parade-goers from their traditional spot at the end of the parade.

 

JINGLE JOLLY JOG 5K

6 p.m. Saturday, Dec. 1, 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. Top-three overall and age-group awards will be given out. There will be a kids’ fun run, as well. The race is held in memory of Allison Gray, a Winter Garden business owner who died in 2016.

The entry fee is $45 through Nov. 30 and $55 check or cash on race day. Registration is available at trinrun.com and at Tri & Run of West Orange, 56 W. Plant St., Winter Garden. The West Orange Junior Service League is the beneficiary.

For information, visit wojsl.com.

 

26TH ANNUAL COOKIE CARNIVAL

8 a.m. to 1 p.m. Saturday, Dec. 1, at the First United Methodist Church of Winter Garden, 125 N. Lakeview Ave. Choose from a wide variety of home-baked cookies for $8 a box.

The Wheeler Class hosts this annual event, which raises money for local mission work. Call (407) 656-1135 for information.

 

WINTER GARDEN FIRE RESCUE SANTA RUN

Between 5:45 and 9 p.m. Dec. 10 through 15 through the neighborhoods of Winter Garden.

Santa Claus will travel through the city’s northwest on Dec. 10; the northeast on Dec. 11; the west side of the County Road 545 corridor of south Winter Garden on Dec. 12; the east side of the County Road 545 corridor of south Winter Garden on Dec. 13; County Road 535 and the Daniels Road corridor of south Winter Garden on Dec. 14; and the Beulah Road and Windermere Road corridor of south Winter Garden on Dec. 15.

The rain makeup date is Monday, Dec. 17.

The Winter Garden Fire Rescue’s annual Santa Run takes Santa and his sleigh on a parade with his firefighter, police and city helpers to spread holiday music, treats and good cheer along the way.

To track Santa, visit WinterGarden-FL.gov.

 

GOLF CART PARADE

4 to 7 p.m. Sunday, Dec. 16, along the historic streets of Winter Garden. Lineup starts at Bradford Park, 220 W. Division St., Winter Garden.

Neighbors can enjoy the parade from their front porch. The golf carts will travel along cart-approved streets and end at the north end of the Walker Field baseball fields at Smith Street and Park Avenue.

Participants should bring a minimum $45 donation (per cart), cash or check, for the West Orange Junior Service League, which will distribute the funds between the Edgewood Children’s Ranch and other West Orange charities.

For details and to register, go to the group’s Facebook page, Christmas Golf Cart Parade. Trailers, alcohol and candy are not allowed.

 

18TH ANNUAL JOHNS LAKE HOLIDAY BOAT PARADE

Approximately 6:45 to 7:15 p.m. Sunday, Dec. 16, on Johns Lake, with viewing from the public boat ramp, 13620 Lake Blvd., Winter Garden. See up to 40 decorated boats on the water. Guests should take lawn chairs or blankets to enjoy the parade.

 

“HOME ALONE” INTERACTIVE FILM AND FUN

Pre-show at 6:30 p.m., movie begins at 7:30 p.m. Sunday, Dec. 16, at the Garden Theatre, 160 W. Plant St., Winter Garden. Celebrate the season with Christmas-themed games, participate in the Ugly Christmas Sweater Contest and test your knowledge in “Finish the Christmas Carol.” Miss P. Tart is the event host.

Tickets are $16 and includes movie, event fees and prop bag. For information, contact the box office at (407) 877-4736 or visit gardentheatre.org. This event is funded by various local arts programs.

 

DE-LIGHT-FUL DECORATIONS CONTEST

Judging begins at 5:30 p.m. Tuesday, Dec. 18, for homes north of West Colonial Drive and Wednesday, Dec. 19, for homes south of Colonial Drive.

Residents wishing to participate in the contest are invited to decorate the exterior of their homes to be judged in one of four categories: Best Overall, Best Theme, Most Original and Best Apartment or Townhome. Cash prizes up to $100 will be awarded.

To download an application, go to cwgdn.com and click on Events. Forms should be returned to the Parks & Recreation office by fax, (407) 656-6504; email, [email protected], or in person, 310 N. Dillard St., by Friday, Dec. 14.

For information, call the Winter Garden Recreation Department at (407) 656-4155.

 

OCOEE

38TH ANNUAL OCOEE LIONS CLUB CHRISTMAS PARADE

1 p.m. Saturday, Dec. 1, with a rain date of 2 p.m. Sunday, Dec. 2. The parade starts at the intersections of Maguire Road and Enterprise Street and ends at Bill Breeze Park, 125 N. Lakeshore Drive.

Folks will line the streets to see festive floats, marching bands, motorcycles, fire trucks, Santa Claus and more. A parade contest for floats, vehicles and walkers will be held. Judges will score participants in the following categories: Youth, Commercial, Non-Commercial, Churches and Judges Overall Winner.

Parade registration forms are available at ocoeelionsclub.org. In lieu of entry fees, parade participants are encouraged to take unwrapped toys that will be donated to the Ocoee Police Department’s Toys for Kids in Need.

 

18TH ANNUAL OPERATION SANTA

5:30 to 8:30 p.m. Dec. 5, 6, 10, 12, 18 and 20. If needed, rain dates will be Dec. 7, 14 and 21.

The Ocoee Fire Department will help Santa Claus and his elves visit the more than 60 neighborhoods tossing candy and spreading holiday cheer to children and families. The toys will be donated to the Ocoee Police Department’s Holiday Toys for Kids in Need drive.

For a complete list of the subdivisions Santa will visit, go to ocoee.org or call the Ocoee Fire Department at (407) 905-3140.

 

OAKLAND

HOLIDAY ARTISAN SHOWCASE

10 a.m. to 4 p.m. Saturday, Dec. 1, at the Oakland Manor House, 620 N. Tubb St., Oakland. Local artists will be demonstrating their craft and offering holiday gifts. Enjoy a history tour, browse the Manor House Gallery and Gift Shop and have some sweets and punch. The free event is open to the public. For information, visit Oaklandmanorhouse.com.

 

LIGHT UP OAKLAND

3:30 to 6 p.m. Saturday, Dec. 1, at the Town Square, 220 N. Tubb St., Oakland. Ring in the Christmas season with this small-town holiday event. Meet Santa Claus from 3:30 to 5:30 and enjoy caroling by the Oakland Avenue Charter School Choir, performances by Centre for Dance & the Performing Arts, children’s activities, food trucks and the 6 p.m. lighting.

WINDERMERE

37TH HOLIDAY SOCIAL

6 p.m., Friday, Nov. 30, at Windermere Town Hall, 520 Main St., Windermere. Locals are invited to Town Hall for a community Christmas party.

 

THE GROVE’S WINTER WONDERLAND

11 a.m. to 2 p.m. Saturday, Dec. 1, at The Grove Orlando, 4744 S. Apopka-Vineland Road, Orlando. The Grove will transform into a winter wonderland with Santa and Mrs. Claus. The plaza will have snow to play in, stilt-walkers, face-painting, train rides and more. The event is free.

 

WINDERMERE BOAT PARADE

5 p.m. Saturday, Dec. 22, beginning at Bird Island and traveling to Lake Butler to Wauseon Bay. Residents are encouraged to deck out their boats in holiday cheer for the annual boat parade. Meet at the north side of Bird Island to prepare for the parade.

 

CHRISTMAS JOY AT WINDERMERE UNION

10 a.m. Sunday, Dec. 9, at Windermere Union Church, United Church of Christ, 10710 Park Ridge-Gotha Road, Windermere. Christmas is about having real joy. The church choir performs a cantata, which takes a look at the true meaning of Christmas. Church music director Kevin Harris conducts all the musical performances of the church.

At 10 a.m. Sunday, Dec. 13, the annual multigenerational Christmas pageant will be presented.  This year’s program is “The Invitation.” Chris Stumpf writes and directs the pageant, as she has in previous years, and the congregation always looks forward to her creative and inspiring story telling.

 

HORIZON WEST

FAMILY ADVENT WORKSHOP

5:30 to 7:30 p.m. Friday, Dec. 7, at Citrus Church – Horizon West, 14111 Shoreside Way, Winter Garden. In this Advent workshop, participants will have a fun and interactive night sharing stories and activities to help prepare families for the Christmas season. There will be a craft, sensory tables and pizza.
The “filing the manger” activity will give children and parents a great way to focus on doing good deeds during the season. The “advent wreath” is a fun way for families to weekly gather together and focus on God. Aprons will be available, but children should dress ready to paint. RSVP at citruschurch.churchcenter.com/registrations/events/177866.

 

WINDERMERE HIGH FOOD TRUCKS AND MOVIE NIGHT

5:30 p.m. Wednesday, Dec. 12, at Windermere High School, 5523, Winter Garden Vineland Road, Windermere. Windermere will host food trucks and a screening of “How the Grinch Stole Christmas.” Proceeds from the event will benefit the WHS Dance Marathon, which will raise money for Children’s Miracle Network.

 

GOTHA

HOLIDAY AMARYLLIS FESTIVAL

9 a.m. to 3 p.m. Saturday, Dec. 8, at Nehrling Gardens, 2267 Hempel Ave., Gotha. This event will feature rare amaryllis bulbs for sale as well as blooming amaryllis and other plants for the holidays. There will be nature-themed vendors, food, music and crafts for the children. Santa and Mrs. Claus will arrive in their red Corvette at 10 a.m. and stay for pictures on the porch until 2 p.m. Enjoy leisurely strolls through the historic home and gardens. [email protected].

 

METROWEST

 ANNUAL METROWEST WINTERFEST

4 to 8 p.m. Saturday, Dec. 8, at MetroWest Golf Club, 2100 S. Hiawassee Road, Orlando. This year’s theme is WinterFest is “Happy Feet.” The event is hosted by the MetroWest Master Association.

For more information, visit Metrowestcommunity.com.

 

DR. PHILLIPS

FAMILY CHRISTMAS MOVIE NIGHT

5:30 p.m. Friday, Dec. 14, at St. Luke’s United Methodist Church, 4851 S. Apopka-Vineland Road, Orlando. Grab your family, friends and neighbors, take your low-back chairs, pillows and inflatable couches and settle in for a night of yuletide and cheer at the church.

This event will feature food, fun and an outdoor screening of Tim Allen’s “The Santa Clause.” Tickets are $10 for a family up to six. For information, call (407) 876-4991.

 

ADVENT LESSONS AND CAROLS

7:30 to 8:30 p.m. Thursday, Dec. 20, at Holy Family Catholic Church, 5125 S. Apopka-Vineland Road, Orlando. The music will cast a sonic light on the birth of Jesus into a dark and weary world, while Holy Family’s readers will boldly proclaim this story.

The free event is open to the public.

 

SOUTHWEST ORANGE

CHRISTMAS WITH THE BASILICA CHOIR

5:30 p.m. gift shop open house, 7:30 p.m. concert Friday, Dec. 7, at the Basilica of the National Shrine of Mary, Queen of the Universe, 8300 Vineland Road, Orlando.

This is an annual tradition of Advent and Christmas music with an audience sing-along of popular holiday tunes. Tickets are $25. For information, call (407) 239-6600 or visit maryqueenoftheuniverse.org.

 

 

author

Amy Quesinberry

Community Editor Amy Quesinberry was born at the old West Orange Memorial Hospital and raised in Winter Garden. Aside from earning her journalism degree from the University of Georgia, she hasn’t strayed too far from her hometown and her three-mile bubble. She grew up reading The Winter Garden Times and knew in the eighth grade she wanted to write for her community newspaper. She has been part of the writing and editing team since 1990.

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