Celebrating the holidays

Whether you’re in the mood for lighting festivals, parades and shopping or holiday music, movies and Santa sightings, December in West Orange County has you covered. Fill your calendar with these holiday events, planned with the entire family in mind.

Here’s your chance to keep with your traditions or maybe start some new ones.

WINTER GARDEN

THURSDAY, DEC. 5

HOLIDAY BOUTIQUE CRAWL

5 to 8 p.m. Thursday, Dec. 5, at nine boutiques in downtown Winter Garden. Enjoy an evening of shopping, sales, sips and snacks. Visit each retailer for an entry into the $200 Visa gift card raffle. Drawing will be at 8:15 p.m. at the gazebo in the plaza. cwgdn.com.

FRIDAY, DEC. 6

32ND ANNUAL LIGHT UP WINTER GARDEN

6 to 9 p.m. Friday, Dec. 6, on and around Plant Street in downtown Winter Garden. Lighting is at 6:15. Join the city as it welcomes the season with live entertainment, vendors, shopping, children’s activities and more. Sponsored by Duke Energy, the West Orange Ministerial Association and the city of Winter Garden. [email protected], (407) 656-4155.

SATURDAY, DEC. 7

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.

COST: $45 through Dec. 6 and $55 check or cash on race day. Registration is available at bit.ly/356ihS2. The West Orange Junior Service League is the beneficiary. Wojsl.com.

A VERY MERRY FARMERS MARKET

9 a.m. to 2 p.m. Saturday, Dec. 7, and continuing Dec. 14 and 21, at the Winter Garden Downtown Pavilion, 104 S. Lakeview Ave. Visit with Santa, attend a wreath-making workshop (there’s a fee), shop for seasonal food and unique gifts, enjoy seasonal food demonstrations and podcasts and try a yoga class. Free. See schedule at wintergardenfarmersmarket.com.

A MERRY WINTER GARDEN LIGHT SHOW

December 7, 13, 14, 15, 20, 21
6 to 9 p.m. Saturday, Dec. 7, and continuing Dec. 13, 14, 15, 20 and 21, at Winter Garden City Hall, 300 W. Plant St. Spectacular animated holiday light show synchronized to music projected onto the front of the building. Free. cwgdn.com, (407) 656-4111.

HOLIDAY CARRIAGE TOURS

5:30 to 9:30 p.m. Saturday, Dec. 7, and continuing Dec. 13, 14, 20 and 21 through downtown Winter Garden. The tours start at the Winter Garden Downtown Pavilion, 104 S. Lakeview Ave. Cost is $65. Reservations are required. soulhavenranch.com, (407) 509-1981.

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.

MONDAY, DEC. 9

WINTER GARDEN FIRE RESCUE SANTA RUN

Between 5:45 and 9 p.m. Monday, Dec. 9, through Saturday, Dec. 14, through the neighborhoods of Winter Garden. The Winter Garden Fire Rescue Department’s annual Santa Run takes Santa and his sleigh on a moving parade around the city.

Santa will be in the city’s northwest on Dec. 9; the northeast on Dec. 10; the west side of the County Road 545 corridor of south Winter Garden on Dec. 11; the east side of the County Road 545 corridor of south Winter Garden on Dec. 12; County Road 535 and the Daniels Road corridor of south Winter Garden on Dec. 13; and the Beulah Road and Windermere Road corridor of south Winter Garden on Dec. 14. The rain makeup date is Monday, Dec. 16. Track Santa at cwgdn.com.

FRIDAY, DEC. 13

HOLIDAY MUSIC AT FRIDAYS ON THE PLAZA

7 to 9 p.m. Friday, Dec. 13, and continuing Dec. 20 and 27, at the Centennial Plaza Gazebo, 101 W. Plant St. A lineup of talented musicians will perform favorite holiday tunes: Dec. 13, Key Harmony; Dec. 20, Roots & Rosin/Nicole Equerme/Abigail Collins; and Dec. 27, Paint it Black Quartet. Free. Cwgdn.com, (407) 656-4111.

SATURDAY, DEC. 14

19TH ANNUAL JOHNS LAKE HOLIDAY BOAT PARADE

7:30 to 8 p.m. Saturday, Dec. 14, at Johns Lake Public Boat Ramp, 13620 Lake Blvd., Winter Garden. See a parade of boats decorated in lights. Take chairs and/or blankets. (407) 701-8033.

MATTHEW’S HOPE COMMUNITY CHRISTMAS CARNIVAL

11 a.m. to 2 p.m. Saturday, Dec. 14, at Matthew’s Hope, 611 Business Park Blvd., Suite 101, Winter Garden. The fun holiday event is open to the community but is geared to the younger homeless and at-risk children in West Orange County. There will be old-time carnival booths with prizes, a Santa’s Shop, visits with Santa Claus and more. (407) 905-9500.

SUNDAY, DEC. 15

GOLF CART PARADE

4 to 7 p.m. Sunday, Dec. 15, along the historic streets of Winter Garden. Lineup is tentatively starting at Bradford Park on Division Street. Neighbors can enjoy the parade from their front porch. The golf carts will travel along cart-approved streets and end at Walker Field baseball fields at Smith Street and Park Avenue. Participants should take a minimum $50 donation (per cart), cash or check, for Edgewood Children’s Ranch. For details and to register, go to the group’s Facebook page, Christmas Golf Cart Parade.

TUESDAY, DEC. 17

DE-LIGHT-FUL DECORATIONS CONTEST

Judging begins at 5:30 p.m. Tuesday, Dec. 17, for homes north of West Colonial Drive and Wednesday, Dec. 18, for homes south of Colonial Drive. Homes will be judged in one of four categories: Best Overall, Best Theme, Most Original and Best Apartment or Townhome. Cash prizes up to $100. 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. (407) 656-4155.

OCOEE

19TH ANNUAL OPERATION SANTA

5:30 to 8:30 p.m. Thursday, Dec. 5, and continuing Dec. 9, 11, 17 and 19, through Ocoee’s more than 60 neighborhoods. If needed, rain dates will be Dec. 6, 13 and 20. The Ocoee Fire Department will help Santa Claus and his elves visit the neighborhoods, tossing candy and spreading holiday cheer to children and families. 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.

FRIDAY, DEC. 6

EVENING WITH SANTA

6:30 to 8:30 p.m. Friday, Dec. 6, at the Ocoee Lakeshore Center, 125 N. Lakeshore Drive. Free pizza dinner and visits with Santa. Children can enjoy letter-writing stations, arts and crafts and more. Preregistration is required, and space is limited to 50 children. Contact Adrian at (407) 905-3180 or [email protected].

SATURDAY, DEC. 7

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.

A parade contest will be held for festive floats, vehicles and walkers. Judges will score participants in several categories, Youth, Commercial, Non-Commercial and Churches; as well as the Overall Winner. The Ocoee Lions Club will present the winners with trophies at the Ocoee City Commission meeting at 6:15 p.m. Tuesday, Dec. 17.

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. Dr. Redding is the 2019 winner of the Grammy Music Educator Award given to one teacher for his or her role in shaping students’ lives through music.

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.

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.

OAKLAND

SATURDAY, DEC. 7

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. oaklandfl.gov.

WINDERMERE

THURSDAY, DEC. 5

WINTER SPECTACULAR

7 p.m. Thursday, Dec. 5, in Windermere High School’s Performing Arts Center, 5523 Winter Garden Vineland Road, Windermere. Fun for all ages with excerpts from “The Nutcracker,” “Frozen” and “Home Alone!” Enjoy ballet, tap, jazz, hip hop and swing, all in less than an hour with a special Rockettes-style finale debuting the Windermere Winderettes. Tickets are on sale now at teachtix.com/whs.

DR. PHILLIPS

FRIDAY, DEC. 6

FAMILY CHRISTMAS MOVIE NIGHT

6 p.m. Friday, Dec. 6, 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 St. Luke’s United Methodist Church. This festive family event at the church will feature food, fun and an outdoor screening of “The Star.” (407) 876-4991.

SUNDAY, DEC. 22

CHANUKAH GRAND COMMUNITY FESTIVAL

4 p.m. Sunday, Dec. 22, at Chabad of South Orlando, 7347 W. Sand Lake Road, Orlando. This free festival, held on the first night of Chanukah, will feature music, fun, food, crafts, raffles, a BMX show and a grand Menorah lighting. JewishOrlando.com.

SUNDAY, DEC. 29

GRAND CAR MENORAH PARADE

5:30 p.m. Sunday, Dec. 29, at Chabad of South Orlando, 7347 W. Sand Lake Road, Orlando. This parade, held on the eighth night of Chanukah, will begin at Chabad and end with a Menorah-lighting celebration near the Premium Outlets. JewishOrlando.com.

GOTHA

SATURDAY, DEC. 14

AMARYLLIS FESTIVAL

9 a.m. to 3 p.m. Saturday, Dec. 14, 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. Be sure to get a photo with Santa and Mrs. Claus after shopping. [email protected].

WINDERMERE

THURSDAY, DEC. 5

WINTER SPECTACULAR

7 p.m. Thursday, Dec. 5, in Windermere High School’s Performing Arts Center, 5523 Winter Garden Vineland Road, Windermere. Fun for all ages with excerpts from “The Nutcracker,” “Frozen” and “Home Alone!” Enjoy ballet, tap, jazz, hip hop and swing, all in less than an hour with a special Rockettes-style finale debuting the Windermere Winderettes. Tickets are on sale now at teachtix.com/whs.

SATURDAY, DEC. 7

THE GROVE’S WINTER WONDERLAND

11 a.m. to 2 p.m. Saturday, Dec. 7, at The Grove Orlando, 4744 S. Apopka-Vineland Road, Orlando. The Grove will transform into a winter wonderland with none other than Santa and Mrs. Claus. The plaza will have snow to play in, stilt-walkers, face-painting, train rides and more. Event is free. Check The Grove’s Facebook for more details.

SATURDAY, DEC. 21

WINDERMERE BOAT PARADE

5 p.m. Saturday, Dec. 21, beginning at Bird Island. 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. (407) 876-2563.

METROWEST

SATURDAY, DEC. 21

METROWEST WINTERFEST

4 to 9 p.m. Saturday, Dec. 21, at the MetroWest Golf Club, 2100 S. Hiawassee Road, Orlando. The MetroWest Master Association is hosting its eighth annual WinterFest, a free, holiday-themed event. It includes Santa Claus parachuting in, "Toy Story 4" shown on the big screen, "Toy Story" characters, photos with Santa and Mrs. Claus, holiday performances by MetroWest and Westpoint elementary schools. games, a skating rink, a snow slide, food truck and vendors. The WinterFest benefits Edgewood Children’s Ranch. metrowestcommunity.com.