- April 18, 2024
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From parades and concerts to family movie nights and ice slides, there’s plenty to do and see during the holidays with the family in the Winter Park/Maitland area. Here’s a guide to the local events happening nearby that will fill your heart with some holiday cheer.
7 p.m. Saturday, Dec. 1, at Central Park at the corner of Park Avenue and Morse Boulevard, Winter Park. The season of events begins with Christmas Movie in the Park, featuring “Christmas with the Kranks” in Central Park. This event is produced by Enzian Theater and will include free popcorn for all attendees. For more information, call (407) 599-3397.
4 to 6 p.m. Sunday, Dec 2, at the Central Park main stage, near the corner of Park and Garfield avenues, Winter Park. The city of Winter Park invites you to celebrate the spirit of the holiday season as the Orlando Philharmonic Orchestra presents its annual Holiday Pops concert in Winter Park’s charming Central Park. Bring a blanket and a picnic and get ready for a concert program of holiday favorites that will be sure to put everyone in the spirit of the season. For more information, call (407) 599-3334.
4 to 7 p.m. Wednesday, Dec. 5, at Casa Feliz, 656 N. Park Ave., Winter Park. Celebrate the holidays with Casa Feliz at its seventh annual holiday open house. The event is sponsored by a grant from Commerce National Bank and Trust in Winter Park. Guests can have photos taken with Santa, enjoy hot cocoa and cookies, admire the decorations at Casa Feliz and enjoy a quartet of Dickensian carolers. There is no charge to attend “Christmas at the Casa,” but a donation of $2 per person or $5 per family is suggested. Professional photos with Santa will be available for $5. For additional information, call (407) 628-8196.
6:15 p.m. Thursday, Dec. 6, at Central Park, near the corner of Park Avenue and Morse Boulevard, Winter Park. The city of Winter Park and The Charles Hosmer Morse Museum of American Art continue a holiday tradition with the 40th annual Christmas in the Park. The two-hour program begins at 6:15 p.m. Central Park creates the beautiful backdrop for the lighting of nine turn-of-the-century Tiffany windows as the Bach Festival Choir performs in concert on the main stage. For more information, call (407) 645-5311.
5 to 10 p.m. Friday, Dec. 7, at Central Park along Park Avenue, Winter Park. The Winter Park Chamber of Commerce and the city of Winter Park are proud to host this kickoff to the holiday season presented by Westminster Winter Park. The holiday street party will include a flurry of activities from 5 to 10 p.m. along Park Avenue and in Central Park. The annual tree-lighting ceremony at dusk will include performances by children’s choirs and children’s activities. For more information, call (407) 599-3399.
7 to 9 p.m. Friday, Dec. 7, at the Central Park main stage, near the corner of Park and Garfield avenues, Winter Park. Presented by Winter Park CRA and produced by Enzian Theater, see a free screening of “Miracle on 34th Street.” Take a blanket, a picnic or snacks, and some family and friends. Free popcorn for everyone. For more information, call (407) 629-0054.
7 to 8:15 p.m. Friday, Dec. 7, at First Congregational Church of Winter Park, 225 S. Interlachen Ave., Winter Park. The experience begins as you follow the star to the manger, rejoice with the angels, hear the music, see the animals in the stable, pay your taxes to the Roman soldiers and enjoy in the marketplace. Your journey concludes with the joy of the manger. Celebrate the hope, peace and joy of the upcoming holiday season at this free event. For more information, call (407) 647-2416.
9 a.m. Saturday, Dec. 8, along Park Avenue, Winter Park. Hosted by the Winter Park Chamber of Commerce, the 66th annual Winter Park “Ye Olde Hometown” Christmas Parade is Central Florida’s longest running Christmas parade. Join the tradition of marching down historic Park Avenue spreading holiday cheer in downtown Winter Park. More than 100 bands, dance troupes, floats, local dignitaries and, of course, Santa Claus, will delight the young and young-at-heart. For more information, call (407) 644-8281.
Select times Monday, Dec. 10, through Thursday, Dec. 13, and Monday, Dec. 17, at various locations. Young and young-at-heart will have the chance to mingle with Old St. Nick himself as he rides his sleigh through Winter Park neighborhoods. Over the five days, Santa will visit Shady Park, Israel Simpson Court and the Winter Park Country Club on Dec. 10; Lake Knowles, East Side and Phelps Park on Dec. 11; Brookshire Elementary, Lakemont Fire Station 62 and Genius and Mizel avenues on Dec. 12; the Park at Orwin Manor, Briarwood Drive, Harland Park (Blueridge Road) and Chelton Circle on Dec. 13; and the DePugh Nursing Center and Margaret Square on Dec. 17. For more information and a detailed schedule with times, call (407) 599-3342 or check the city’s calendar at cityofwinterpark.org/events/2018-12.
6 to 9 p.m. Friday, Dec. 14, and 9 a.m. to 1 p.m. Saturday, Dec. 15, at the Central Park West Meadow at the corner of New York Avenue and Morse Boulevard, Winter Park. Gather your family and friends for the city’s inaugural “Snow in the Park.” Kids of all ages will be able to glide down giant ice slides, play in snow flurries or tinker in Santa’s workshop. Everyone will be able to warm up with delicious S’mores and hot chocolate, both available for purchase. For more information, email [email protected] or call (407) 599-3342.
3 to 8 p.m. Saturday, Dec. 15, at the Rollins College Beach Front and Student Center; Dinky Dock. Witness a water ski show and competition on Lake Virginia with a variety of skills on display, followed by the boat parade comprising decorated boats from homeowners on Lakes Virginia, Osceola and Maitland. The event is sponsored by Winter Park Rotary Club in partnership with Rollins College. The event will raise funds for food pantries at Winter Park High School and Killarney Elementary School. For more information, call (407) 399-1296.
2 and 6 p.m. Saturday, Dec. 15, and Sunday, Dec. 16, at Knowles Memorial Chapel, 1000 Holt Ave., Winter Park. Hear Christmas classics performed by the incomparable Bach Festival Choir, Youth Choir and Orchestra in beautiful Knowles Memorial Chapel, led by conductor John V. Sinclair. Tickets are $35 to $79. For more information, call (407) 646-2182.
Through Sunday, Dec. 16, at select showtimes at The Winter Park Playhouse, 711 Orange Ave., Suite C, Winter Park. The well-loved Wonderettes, created by Roger Bean, are back and better than ever. This whimsical musical comedy finds the four-girl singing group entertaining at the annual Harper’s Hardware Holiday Party. When Santa goes missing, they use their charm, talent and creative ingenuity to save the day. Tickets are $15-$42. For more information, call (407) 645-0145.
8 p.m. Saturday, Dec. 15, Monday, Dec. 17, and 3 p.m. Sunday, Dec. 16, at the Blue Bamboo Center for the Arts, 1905 Kentucky Ave., Winter Park. “One Man — A Christmas Carol” is written and performed by David A. McElroy. Mr. McElroy adapted “A Christmas Carol” for the stage and performs all 37 different characters. The play is directed by Marylin McGinnis, with stage management by Bonnie Sprung. Tickets are $20. For more information and to buy tickets, visit bluebambooartcenter.com.
1 p.m. Saturday, Dec. 22, at the Central Park main stage, on the corner of Park and Garfield avenues, Winter Park. Enjoy the rich sounds of Christmas as tuba, euphonium, sousaphone and baritone players of all ages gather in Central Park to perform a free concert from the main stage beginning at 1 p.m. Winter Park’s 23rd annual Merry Tuba Christmas is a free one-hour concert that has become a staple on the holiday list of things to do. Registration is $10 for musicians and begins at 9 a.m. with rehearsal running from 10 am to 11:30 a.m. For more information, call (407) 599-3463.
Noon to 1 p.m. Friday, Nov. 30, at Maitland Public Library, 501 Maitland Ave. S., Maitland. Come see a free screening of “Elf.” For more information and a complete list of holiday movies throughout the month, call (407) 647-7700 or visit maitlandpubliclibrary.org.
5 to 10 p.m. Saturday, Dec. 1, at Lake Lily Park, 701 Lake Lily Drive, Maitland. This family event will feature music, food vendors, fireworks, a snow slide and Santa. Performers include the Maitland Middle School Orchestra and Chorus, the Dommerich Elementary School Choir, Ballet South and the Colby Center for Dance. Admission is free. For more information, call the city hall front desk at (407) 539-6200.
6 p.m. Saturday, Dec. 15, at theMaitland Middle School Soccer Field, 1901 Choctaw Trail, Maitland. Enjoy a free screening of the “The Polar Express.” For more information, call the city hall front desk at (407) 539-6200.
Wednesday, Dec. 19. Children ages 8 or younger can receive a phone call from Santa Claus if they submit information to [email protected] by Monday, Dec. 10.
6 p.m. Monday, Dec. 24, at Venue on the Lake, 641 S Maitland Ave, Maitland. Enjoy this Christmas service hosted by Anchor Church. Call (407) 539-6200.
