Holiday Events in Winter Park: Your Guide to Festive Fun
The holidays in Winter Park sparkle a little brighter each year, thanks to the city’s charming streets, lively community spirit, and a calendar full of celebrations hosted by the Winter Park Chamber of Commerce and its members. From classic parades to enchanting concerts, Winter Park transforms into a festive wonderland throughout December. Whether you’re a longtime resident or visiting for the season, here’s how to experience the best of the holidays around Winter Park.
Saturday, November 15 – Sunday, November 23, 2025 | Orlando Museum of Art
Step into a winter wonderland of dazzling holiday décor at the Orlando Museum of Art’s annual Festival of Trees. Each gallery transforms into a festive showcase of designer-decorated trees, wreaths, and holiday vignettes, all created by local artists and designers. Guests can shop for unique gifts, enjoy live entertainment, and soak in the magic of art and the holidays combined. Learn more about Festival of Trees here.
Fridays, November 28 – December 26, 2025 | 5:00 – 8:00 p.m. | The Charles Hosmer Morse Museum of American Art
Kick off your holiday journey with this elegant and relaxing museum celebration at the Charles Hosmer Morse Museum of American Art. Visitors enjoy free admission each Friday evening and can take in live music in the art-filled galleries surrounded by Tiffany glass, soft lighting, and warm seasonal ambiance. A perfect way to pause, reflect, and soak up the holiday mood. Learn more about Friday Nights at the Morse here.
Friday, December 5, 2025 | 5:00 – 9:00 p.m. | Park Avenue
Kick off the season with Winter Park’s most beloved tradition, Winter on the Avenue. On Friday evening, Park Avenue and Central Park come alive with twinkling lights, music, and laughter as families gather for the city’s official tree lighting. Enjoy live entertainment, festive treats, and even a visit from Santa and Mrs. Claus. Children can slide down the snow slope or toast s’mores under the stars while carolers fill the night air with holiday cheer. This free community celebration truly captures the spirit of Winter Park: joyful, welcoming, and full of heart. Learn more about Winter on the Avenue here.
Saturday, December 6, 2025 | 7:00 – 10:00 a.m. | Central Park
Start your Saturday with a hearty pancake breakfast served by the team behind the event in Central Park. Enjoy live music, family-friendly fun, and help support local youth and adult leadership programs in Winter Park. A delightful early-morning holiday tradition. Learn more about the LWP Pancake Breakfast here.
Saturday, December 6, 2025 | 9:00 – 10:30 a.m. | Park Avenue
Nothing says “holiday spirit” like the Winter Park Christmas Parade, now in its 73rd year. Known as “Ye Olde Hometown Parade,” this cherished event winds its way down Park Avenue with dazzling floats, marching bands, and community groups spreading cheer. Families line the sidewalks with coffee and cocoa in hand, waving as the parade ushers in the magic of the season. It’s a tradition that beautifully blends nostalgia with hometown pride. Learn more about the 73rd Annual Winter Park Christmas Parade here.
Sunday, December 7, 2025 | 3:00 p.m. | Dr. Phillips Center for the Performing Arts
The Orlando Philharmonic Orchestra fills the Dr. Phillips Center with the sounds of the season during Holiday Harmonies. Expect a blend of classical favorites and festive carols performed by world-class musicians. Learn more about Holiday Harmonies here.
Wednesday, December 10, 2025 | 6:00 p.m. | Albin Polasek Museum & Sculpture Gardens
Step into the charm of the 1920s at the Albin Polasek Museum & Sculpture Gardens for Polasek Nights – A Holiday Speakeasy. This enchanting evening features live jazz, festive cocktails, and sparkling lights illuminating the museum’s lakeside gardens. Guests are invited to mingle among sculptures, enjoy seasonal bites, and soak in the elegant atmosphere of this beloved holiday tradition. Learn more about Polasek Nights – A Holiday Speakeasy here.
Friday, December 12 – Monday, December 22, 2025 | Orlando Family Stage
Bring the whole family to Orlando Family Stage for a heartwarming performance of A Charlie Brown Christmas. This live adaptation of the classic story captures the charm, humor, and message of the beloved Peanuts tale, reminding audiences of the true meaning of the holidays. Learn more about A Charlie Brown Christmas here.
December 5–24, 2025 | Dr. Phillips Center for the Performing Arts
For a touch of elegance, don’t miss Orlando Ballet’s production of The Nutcracker at the Dr. Phillips Center for the Performing Arts. This timeless ballet brings Tchaikovsky’s score to life through breathtaking choreography, glittering costumes, and a sprinkle of holiday magic. It’s a must-see performance for families, couples, or anyone looking to make their season sparkle. Learn more about The Nutcracker here.
Sunday, December 14, 2025 | 5:30 – 8:30 p.m. | Mead Botanical Garden
The Mead Botanical Garden transforms into a twinkling wonderland for Seasons Greetings from the Garden. Stroll through beautifully lit pathways, enjoy seasonal performances, and savor the peaceful glow of the gardens on a cool winter evening. Learn more about Seasons Greetings from the Garden here.
Monday, December 15, 2025 | 4:00 p.m. | Central Park
Celebrate the season with Holiday Pops in Winter Park, a community concert that brings residents together for an afternoon of music, laughter, and good cheer. The Orlando Philharmonic Orchestra performs beloved holiday classics under the open sky. Learn more about Holiday Pops in Winter Park here.
Saturday, December 13, 2025, at 7:30 p.m.
Sunday, December 14, 2025, at 2:00 p.m.
Experience the serenity of the season with the Bach Festival Society of Winter Park Their annual A Classic Christmas concert at Knowles Memorial Chapel fills the space with rich choral harmonies and orchestral arrangements. The concert’s warmth and reverence remind us of the beauty of tradition and togetherness during the holidays. Learn more about A Classic Christmas here.
Wednesday, December 24, 2025 | 5:00 – 8:00 p.m. | The Charles Hosmer Morse Museum of American Art
Spend Christmas Eve surrounded by art and light at The Morse Museum. The museum offers free admission and live holiday music, inviting guests to reflect and celebrate the beauty of the season. Learn more about the Christmas Eve Celebration here.
Throughout December 2025 | Winter Park Chain of Lakes
Set sail on the Winter Park Chain of Lakes aboard The Original Orlando Tours’ Old-Fashioned Christmas Cruise. This scenic experience features festive décor, twinkling lights, and narration highlighting Winter Park’s history and holiday charm. Learn more about The Winter Park Old-Fashioned Christmas Cruise here.
Stroll, Shop, and Celebrate on Park Avenue
Between major events, the charm of Park Avenue never fades. The tree-lined streets shimmer with holiday lights, local shops showcase unique gifts, and restaurants offer seasonal menus ideal for cozy gatherings. Take a leisurely stroll, stop for a cup of cocoa or a glass of wine, and soak up the festive atmosphere that makes Winter Park one of Central Florida’s most enchanting holiday destinations.
Experience the Spirit of the Season
Whether you’re watching the parade, admiring the art at The Morse, or enjoying a performance of The Nutcracker, Winter Park offers endless ways to celebrate. These events not only highlight the city’s vibrant arts and culture scene but also embody the warmth and generosity that define the community. This holiday season, make time to gather, give, and create lasting memories in the heart of Winter Park.
