Check out the flurry of sparkling events this holiday season in Winter Park
- Alastair Mac
- 27 minutes ago
- 7 min read
Mark your calendars and make it a season to remember in Winter Park with tons of things to do throughout the holidays.
The City of Winter Park is preparing to welcome a flurry of fun events for all the family this holiday season, so mark your calendars, don your holiday apparel and gather with loved ones to experience these annual Winter Park traditions.
Downtown Winter Park will start sparkling with lights Thursday, November 13. This year, the
downtown décor aims to bring the magic of the holidays to life for both residents and guests.
Festive décor will sparkle along Park Avenue including 150,000 lights, festive wreaths on lamp posts, a cathedral of lights in Central Park, children’s carousel beginning November 29, and so much more. For more information about the Park Avenue District’s cathedral or carousel please access parkavenuedistrict.com.
On Thursday, November 20, Friends of Hannibal Square present the 4th Annual Taste of
Hannibal Square. From 5 to 9 pm, you can enjoy dining with tasting plates from local restaurants
while listening to live music on West New England Avenue. Tasting plate tickets can be purchased in advance via Eventbrite or at the event. In partnership with Winter Park’s Community Redevelopment Agency (CRA), proceeds will benefit the Welbourne Nursery and Preschool. For more information, please access iluvhannibalsquare.com.
The city’s Parks & Recreation Department invites the community to enjoy Light Up Seven Oaks on
Saturday, November 22, from 5 to 8 pm. in Seven Oaks Park. Shop local vendors for all your
holiday gifts and enjoy live music. The countdown for the electric Christmas tree lighting will begin at 6 pm. For more information about the event, please call 407-599-3342.
Also presented by the city’s Parks & Recreation Department, Holiday Movie Night at Seven Oaks
will feature A Christmas Story at 7 pm on Friday, November 28, in Seven Oaks Park. Pack a
lawn chair or blanket and enjoy a cozy evening under the stars with food trucks in the park from 6 to 9 pm. For more information, please call 407-599-3342.
The Charles Hosmer Morse Museum of American Art will offer free admission on Fridays in December, including Friday, November 28 and December 5, 12, 19 and 26, from
4 to 8 pm, and feature live music from 5 to 8 pm, for its Holiday Friday Nights at the Morse. In
addition, Christmas Eve will feature free museum admission from 9:30 am to 4 pm, with live music
from 1 to 4 pm. For more information, please access morsemuseum.org.
Check out the latest Christmas and Holiday News from throughout Central Florida. From the theme parks, to the attractions, shopping malls and resort hotels, you will be dazzled with holiday cheer, including the most spectacular events at the theme parks and attractions, glittering community events and parades, plus, magical parties, eats and treats, and so much more!
The City of Winter Park and The Charles Hosmer Morse Museum of American Art continue a holiday tradition with the 47th Annual Christmas in the Park, Thursday, December 4.
The two-hour program begins at 6:15 pm in Central Park, creating the beautiful backdrop for the
lighting of turn-of-the-century Tiffany windows as the Bach Festival Choir, Brass Ensemble and Youth Choir perform in concert on the main stage. For more information about the event, please access morsemuseum.org/programs-events/christmas-in-the-park.
On Friday, December 5, from 5 to 9 pm, the festivities continue as the Winter Park Chamber of
Commerce and the City of Winter Park host Winter on the Avenue. This holiday street party will
feature an array of activities including the Annual Tree Lighting Ceremony, presenting
the city’s Christmas tree in Central Park, a symbolic Menorah lighting, a Kwanzaa Kinara display,
Santa & Mrs. Claus, Popcorn Flicks in the Park, live music, snow slides from the Parks & Recreation Family Fun Program, s’mores from the Winter Park Fire-Rescue Department, and so much more. For additional information, please call 407-644-8281 or access winterpark.org.
Presented by the CRA and produced by Enzian Theater, Popcorn Flicks in the Park, featuring
Frozen preceded by Frosty’s Winter Wonderland, will take place in Central Park, Friday,
December 5, at 7 p.m. Bring your family and friends, and don’t forget to pack a blanket, picnic or
snacks. For more information, please call 407-599-3342.
On Saturday, December 6, Park Avenue comes to life at 9 am, with the 73rd Annual
Winter Park “Ye Olde Hometown” Christmas Parade, hosted by the Winter Park Chamber of
Commerce. This family-friendly occasion showcases holiday-themed floats, Santa Claus
and well-known local figures as they make their way down the avenue. The parade begins at Canton Avenue and will travel down Park Avenue, ending at the intersection of Lyman and Park avenues. Emceed by FOX 35’s John Brown, the parade will be live-streamed on the Chamber’s Facebook page and broadcast on FOX 35 local. For more information, please call 407-644-8281 or access winterpark.org.
Before and during the Christmas Parade Saturday, December 6, Leadership Winter Park will host
the Annual Leadership Winter Park Pancake Breakfast, at the Central Park Main Stage from 7 to
10:30 am. Enjoy pancakes, sausage and beverages for just $7 per person. Proceeds benefit the
Winter Park Improvement Foundation to provide scholarships for adult and youth leaders enrolled in Leadership Winter Park programs. For more information and to purchase tickets, please access
On Wednesday, December 10, from 5 to 7 pm, bring the kids to the Winter Park Fire-Rescue
Department’s Station 61, located at 343 W. Canton Ave., for a Santa Shift Open House. Enjoy arts
and crafts, explore the trucks, try on Firefighter gear and meet Firefighter Claus! For more
information, please call 407-599-3317.
On Friday, December 12, from 5 to 8 pm, wear your favorite holiday sweater and head to Hannibal
Square Heritage Center for the 6th Annual Light Up Hannibal Square. Bring your camera for a free
photo with Santa Claus, enjoy a holiday concert by international vocalist Maria O. Bryant and band
from 6:30 to 7:30 pm, the holiday light countdown will begin at 6 pm outside the Heritage Center.
For more information, please access hannibalsquareheritagecenter.org.
Wreaths Across America will be at Palm and Pineywood cemeteries Saturday, December 13, at
noon, to remember and honor veterans by the laying of Remembrance Wreaths on the markers of our country’s fallen heroes. To order a wreath or volunteer to participate, please access
A special Holiday Pops concert, performed by the Orlando Philharmonic Orchestra, will take place
Saturday, December 13, at 6 pm, on the Central Park Main Stage. Bring your blanket and a picnic
for a concert program of holiday favorites that will be sure to put everyone in the spirit of the season. This free concert is made possible by the Charlotte Julia Hollander Trust. For more information, call 407-599-3342.
The holiday festivities move from the city streets to Lake Virginia as the Winter Park Holiday Boat
Parade, hosted by the Winter Park Rotary Club and the city’s Natural Resources & Sustainability
Department, sets sail Saturday, December 13, at 6 pm. Before the boat parade launches, Natural
Resources & Sustainability will be hosting a Boat Parade Watch Party at 5 pm in Dinky Dock Park.
Enjoy music, giveaways and festive treats while you watch the boat parade cruise by. Bring your own lawn chair or grab a seat on the bleachers. To register a boat in the parade, please access
cityofwinterpark.org/boat-parade-register or call 407-256-6369. For more information about the
watch party, call 407-599-3463.
Chabad of Greater Orlando will present Chanukah on the Park Sunday, December 14, at
5:30 pm, in Central Park. The event will feature America’s Got Talent runner-up Roni & Rhythm, live music, a snow experience, kids’ activities, food and grand menorah lighting. For more information, access chabadorlando.org.
The Great American Big Band will be bringing the sounds of Christmas to the Central Park Main
Stage at 7 pm, Friday, December 19. Grab your chairs, pick up food from your favorite restaurant,
and enjoy a holiday concert under the stars. For more information, greatamericanbigband.com.
Enjoy the rich sounds of Christmas as tuba, euphonium, sousaphone and baritone players of all ages gather to perform a FREE concert from the Central Park main stage at 1 pm, Saturday, December 20. Hosted by the city’s Natural Resources & Sustainability Department, Winter Park’s Merry Tuba Concert is a must-see on the holiday list of things to do. Registration for musicians begins at 9 a., with a rehearsal at 10 am. Performers, please bring a folding chair and music stand. For more information, call 407-599-3463.
On Friday, December 26, from 5 to 9 pm, the Equity Council Corp. is hosting its Annual Kwanzaa
Celebration at the Winter Park Community Center, sponsored by the city’s Parks & Recreation
Department. Enjoy food, drumming, special dance and musical performances, and support small
businesses by shopping the SOKO Marketplace. This year’s celebration will commence with the
lighting of the black candle and focus on the Kwanzaa principle of Umoja (Unity). Tickets are available in advance and at the event. For more information, access equitycouncilcorp.org.
To see a full lineup of all the upcoming holiday festivities in Winter Park, check out cityofwinterpark.org/holiday-events.
Before attending any of the events listed on Gotta Go Orlando, you should contact the organizer or venue to confirm that the event is taking place as information, changes, and cancellations can occur.
Never miss anything happening in Orlando again, we've got you covered with the latest and best things to see and do throughout Central Florida. Get the Latest Orlando News now!
Contact Us:
You can contact us here. To advertise with us, click here. To list your upcoming event, submit it here.
Newsletter:
Sign up for our newsletter and stay in the loop with all the latest news from Central Florida delivered daily to your mailbox.
Social Media:
Join the local conversation on X, Facebook, and Instagram, plus, for extended coverage, catch the latest on our YouTube channel.
