It's beginning to look a lot like Christmas! Get in the spirit with these upcoming holiday events

West Orange and Southwest Orange residents have plenty of opportunities to celebrate the season.


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WINTER GARDEN
ONGOING
FOUNDATION ACADEMY SHOEBOX COLLECTION

The “Our Christians in Service” club at Foundation Academy’s Tilden Campus has been collecting supplies and shoeboxes for the annual New Missions Haiti Shoebox Drive. More boxes are needed, and the Plant Street Campus is collecting through Dec. 8. Visit bit.ly/3rsW2Ei.

CITY HALL LIGHT SHOW
The lights display is 6 to 9 p.m. Dec. 4, 10-12, 17-19, 23.

‘BIG, THE MUSICAL’
“Big, the Musical” appears on the stage of the Garden Theatre, 160 W. Plant St., through Dec. 10. Visit gardentheatre.org.

HORSE-DRAWN CARRIAGE TOUR
Rides are available from 5:30 to 9:30 p.m. Dec. 4, 10-11, 17-19, 22-24, 26, 27, 28, 29 and 30. Reservation/fee required. (407) 656-4111.

WINTER GARDEN FIRE RESCUE SANTA RUN
Between 5:45 and 9 p.m. Dec. 13 to 18, the Winter Garden Fire Rescue Department will escort Santa Claus through the neighborhoods of Winter Garden. An alternate date is scheduled for Dec. 20 if weather interrupts one of Santa’s visits. Santa will be in the city’s northwest on Dec. 13; the northeast on Dec. 14; the west side of the County Road 545 corridor of south Winter Garden on Dec. 15; the east side of the County Road 545 corridor of south Winter Garden on Dec. 16; County Road 535 and the Daniels Road corridor of south Winter Garden on Dec. 17; and the Beulah Road and Windermere Road corridor of south Winter Garden on Dec. 18. 

DE-LIGHT-FUL DECORATIONS CONTEST
Festive presentations of outdoor decorations could win up to $100. Register at cwgdn.com. Judging begins at 5:30 p.m. Tuesday, Dec. 14, and Wednesday, Dec. 15.

FRIDAY, DEC. 3
LIGHT UP WINTER GARDEN

6 to 9 p.m. Friday, Dec. 3, on Plant Street, downtown Winter Garden. Join Winter Garden as it welcomes the season with the lighting of downtown, live entertainment, vendors, shopping, children’s activities and more. 

SATURDAY, DEC. 4
WINTER GARDEN CHRISTMAS PARADE

10 a.m. Saturday, Dec. 4, in downtown Winter Garden. The parade begins on South Dillard Street, heads north and goes west on Plant Street.

12TH ANNUAL JINGLE JOLLY JOG 5K
6 p.m. Saturday Dec. 4, in Oakland Park. Run or walk this evening race among the festive holiday decorations through the community in Winter Garden. Visit wojsl.com.

SUNDAY, DEC. 5
HARP CONCERT

4 p.m. Sunday, Dec. 5, at the First United Methodist Church of Winter Garden, 125 N. Lakeview Ave. The Central Florida Chapter of the American Harp Society will perform holiday music. Masks are required for this event. Tickets are a suggested donated of $5. (407) 656-1135.

THURSDAY, DEC. 9
HOLIDAY BOUTIQUE STROLL

5 to 8 p.m. Thursday, Dec. 9, in downtown Winter Garden. Make shopping a fun holiday experience with special sale offers and complimentary sips and snacks in downtown Winter Garden. Visit cwgdn.com.

SATURDAY, DEC. 11
CHRISTMAS SPECTACULAR

6 to 9 p.m. Saturday, Dec. 11, at Gymnastics USA, 13175 W. Colonial Drive, Winter Garden. This event will feature food Trucks, a Santa visit, family open gym, vendors, rock climbing, a deejay, raffles and prizes, snow fall, and more. Visit gymnasticsusa.us/christmas.

SUNDAY, DEC. 12
WINTER GARDEN GOLF CART PARADE

5:30 p.m. Sunday, Dec. 12, beginning at Dr. Bradford Memorial Park. Get ready for a different kind of parade when dozens of decorated golf carts roll through downtown. Visit facebook.com/wgchristmasgolfcartparade.

SUNDAY, DEC. 12
GARDEN CHOIR HOLIDAY CONCERT 

7:30 p.m. Sunday, Dec. 12, at the Garden Theatre, 160 W. Plant St., Winter Garden. The Orlando Choral Society presents The Winter Garden Community Choir & Voci del Cuore (Voices of the Heart), perform classic Christmas music. Free; reservations required. Patrons wishing to donate can reserve seats and purchase a $5 suggested donation ticket at gardentheatre.org/more.

21ST ANNUAL JOHNS LAKE HOLIDAY BOAT PARADE
7:30 p.m. Sunday, Dec. 14, at Johns Lake. Spectators should take chairs or blankets to the Johns Lake Public Boat Ramp, 13620 Lake Blvd., Winter Garden. Visit bit.ly/3kue2tJ.

SATURDAY, DEC. 18
ANNUAL SANTA BIKE RIDE

3 to 5 p.m. Saturday, Dec. 18, beginning at Winter Garden Wheel Works, 101 W. Plant St. Riding two miles at a casual pace, riders will be caroling and strolling the streets, with Santa himself leading the ride. Helmets and lights will be required; it will be dark around this time. Visit facebook.com/wgwheelworks.

SUNDAY, DEC. 19
‘FINDING CHRIST IN CHRISTMAS SPECIALS’

5 p.m. Sunday, Dec.19, at the First United Methodist Church of Winter Garden, 125 N. Lakeview Ave. Rudolph, Frosty and The Grinch — the most beloved Christmas characters of all time —illustrate timeless truths in this interactive one-man show by Jason Korsiak. Free. (407) 656-1135.

OCOEE
ONGOING
21ST ANNUAL OPERATION SANTA

Jolly Old Saint Nicholas will ride through Ocoee neighborhoods aboard a festive holiday float built by the Ocoee Fire Department and volunteers. When the holiday float arrives in neighborhoods, residents are encouraged to give Santa new, unwrapped toys. The toys will be donated to the Ocoee Police Department’s Holiday Toys for Kids in Need drive. Santa will travel the streets from 5:30 to 8:30 p.m. Dec. 2; 6 to 8:30 p.m. Dec. 7; 5:30 to 9 p.m. Dec. 9; 5:30 to 8 p.m. Dec. 14; and 5:30 to 9 p.m. Dec. 16. If needed, rain dates will be Dec. 3, 10 and 17. For a complete list of subdivisions, visit ocoee.org/OperationSanta.

FRIDAY, DEC. 3
EVENING WITH SANTA

6:30 to 9 p.m. Friday, Dec. 3, at the Ocoee Lakeshore Center, 125 N. Lakeshore Drive. Join the city of Ocoee for a meet-and-greet with Santa. Space is limited, and pre-registration is required at [email protected] or (407) 905-3180.

SATURDAY, DEC. 4
HOLIDAY TREE LIGHTING 

4 to 6 p.m. Saturday, Dec. 4, at the Ocoee Lakeshore Center, 125 N. Lakeshore Drive. Ocoee’s annual Holiday Tree Lighting will feature the countdown to the tree lighting, Santa’s Village, a kids zone and more. Visit ocoee.org.

SATURDAY, DEC. 11
BREAKFAST WITH SANTA

9 a.m. Saturday, Dec. 11, at the Ocoee Lakeshore Center, 125 N. Lakeshore Drive. Visit Santa and his special guest, share Christmas wishes and take pictures. Indoor and outdoor seating options are available. Space is limited; register early at [email protected] or (407) 905-3180. Cost is $5 per person. 

OAKLAND
ONGOING
TREES OF THE SEASON

Oakland is hosting its first holiday tree-decorating contest, “Trees of the Season,” at the Healthy West Orange Arts and Heritage Center at the Town of Oakland, 126 Petris Ave. Families, schools, non-profits organizations and businesses can participate. “Trees of the Season” will be on display through Jan. 3. Interested participants can email arts&[email protected].

THURSDAY, DEC. 2
HANUKKAH CELEBRATION

3 to 5 p.m. Thursday, Dec. 2, at the Healthy West Orange Arts and Heritage Center at the Town of Oakland, 126 Petris Ave. Join Jay Marder, a rock, folk, blues and klezmer musician, and sing along to your favorite Hanukkah songs on the porch. Additionally, step inside to view some of Marder’s personal collection of Judaica as part of the “Places of Worship” exhibit, on display through Jan. 14, 2022. Visit oaklandfl.gov.

SATURDAY, DEC. 4
2021 SANTA’S LANE

3 to 6 p.m. Saturday, Dec. 4, in Oakland’s Historic Town Center at Tubb Street. Spend a few hours with Santa and his elves, pose for photos and take home a special treat from the North Pole (while supplies last). Santa’s route will be posted at oaklandlf.gov and on Facebook. 

HORIZON WEST
ONGOING 
HAMLIN HOLIDAYS FAIR

Celebrate the season with thrill rides, a Kiddieland for children, fair food and skill games from Dec. 3 to 19 at 16313 New Independence Parkway.

SATURDAY, DEC. 4
HOLIDAY MARKET AT HAMLIN

10 a.m. to 2 p.m. Saturday, Dec. 4, at Hamlin Town Center, 14111 Shoreside Way, Winter Garden. Shop local and have some holiday fun at this market, presented by Legacy Events for Education. Visit legacyeventsfored.org.

SATURDAY, DEC. 11
DREAM FINDERS HOMES12KS OF CHRISTMAS

7:30 a.m. Saturday, Dec. 11, at Hamlin Town Center, 14111 Shoreside Way. Don’t miss this fun, Christmas-themed run the whole family can enjoy. Register at floridarunningco.com/12ks-of-christmas.

SANTA’S COMING TO HAMLIN
10 a.m. to 2 p.m. Saturday, Dec. 11, at Hamlin Town Center, 14111 Shoreside Way, Winter Garden. Join neighbors for an afternoon of family fun, crafts, music and pictures with Santa.

CAST MEMBER PANTRY'S HOLIDAY FESTIVAL
Noon to 5 p.m Saturday, Dec. 11, at 8464 Winter Garden Vineland Road, Orlando. Join the pantry for a day with games, food, local vendors and, of course, Santa Claus and Mrs. Claus. All proceeds benefit families in need.

SUNDAY, DEC. 12
APARTMENT 20 EVENTS HOLIDAY MARKET AT HAMLIN

Noon to 6 p.m. Sunday, Dec. 12, at Hamlin Town Center, 14111 Shoreside Way, Winter Garden. This event will feature vendors, music, a kid zone and more.

LAKE HANCOCK BOAT PARADE
4 p.m. Sunday, Dec. 12, at the Overlook Boat Ramp. Register your boat for a parade on Lake Hancock. Entry into the parade is an unwrapped toy to be donated to one of two children’s charities. 

DR. PHILLIPS
SATURDAY, DEC. 4
CHRISTMAS CONCERT: ‘A GIFT FOR THE KING’

5:30 and 7:30 p.m. Saturday, Dec. 4; and 5:30 p.m. Sunday, Dec. 5, at St. Luke’s United Methodist Church, 4851 S. Apopka-Vineland Road, Orlando. Tickets are $12 for adults and $6.50 for children under 12. Visit st.lukes.org.

GOTHA
SATURDAY, DEC. 11
10TH ANNUAL HOLIDAY AMARYLLIS FESTIVAL

9 a.m. to 3 p.m. Saturday, Dec. 11, at Nehrling Gardens, 2267 Hempel Ave., Gotha. The gardens will feature beautiful and rare amaryllis bulbs for sale, as well as blooming amaryllis and other plants for the holidays. Contact [email protected].

WINDERMERE
SATURDAY, DEC. 18
WINDERMERE BOAT PARADE

5 p.m. Saturday, Dec. 18, on the Butler Chain of Lakes. Residents are encouraged to deck out their boats in holiday cheer for the annual Windermere Boat Parade. Participants should meet at the north side of Bird Island to prepare for the parade.

 

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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