Starlight Nights is Winter Haven’s Holiday tradition – a festival of lights celebrating the Holidays and the city’s wonderful Historic Downtown District.
Starlight Nights with 22,000 Lights
From December 4 through early January visitors can experience the magic of the Holiday’s with over 22,000 lights! Downtown Winter Haven will be lit up from 5:30-10:00PM each night. Decorations will cover the Historic District, from US-17 to Lake Silver, and Central Avenue to 6th Street.
No Holiday festival would be complete without Santa and other magical photo opportunities! In addition to the lights and special appearances, Downtown business owners will be creating magical window displays as part of a window decorating contest. You’ll even find selfie stations in the park.
Holiday Events Happening in Downtown Winter Haven
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Shop Small Saturday – November 29, 2025
Main Street Winter Haven proudly hosts Small Business Saturday, a festive event dedicated to supporting the local community. Embraced by the spirit of small businesses this event takes place in Historic Downtown Winter Haven. Check out each business participating with their specials and business hours!
Tree Lighting Ceremony – December 4, 2025
The City of Winter Haven in coordination with Main Street Winter Haven will host the City’s Annual Tree Lighting in Central Park located in beautiful Historic Downtown Winter Haven. Enjoy Hunter Smith singing Christmas carols and Holiday hits! The first 100 children will enjoy free hot cocoa from Richard’s Fine Coffee and cookies courtesy of Gourmet Goodies!
- 6-6:30 pm – Enjoy hot Cocoa & Cookies (First 100 kids)
- 6:00-7 pm – Enjoy live music
- 7 pm – The official countdown for the Tree Lighting with special guests followed by a Holiday sing-a-long
Downtown Winter Haven First Friday – December 5, 2025
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Holidays on Central – December 6, 2025
Destroyer Media is bringing back Holidays on Central (formerly Carols in the Park hosted by Main Street Winter Haven). This event carries the community’s favorite holiday tradition forward for the next generation. Thousands of guests will descend upon downtown Winter Haven to enjoy live entertainment, specialty foods, interactive experiences and two holiday markets – a traditional Mistletoe Market and local favorite, Bandit Market.
Grinchmas at Gourmet Goodies – December 12, 2025
Grab photos with the Grinch at Gourmet Goodies. Enjoy yummy Grinch treats and costume contests and prizes!
Winter Haven Wonderland – December 12, 2025
Step into the magic of the season at Winter Haven Winter Wonderland!
Bring the whole family for an evening filled with festive fun, holiday lights, and community cheer in the heart of Downtown Winter Haven. Enjoy free pictures with Santa (6:30–8:30 PM), a special showing of The Polar Express under the stars, and a variety of kids’ activities including ornament decorating, letters to Santa, and inflatable fun zones.
Deck the Yard at Bowen Yard – December 13, 2025
They aren’t just decking the halls this year, Bowen Yard in Winter Haven is decking the yard starting at 2pm. Enjoy drink deals from restaurants, a hot cocoa bar, chocolate chip cookies, taco deals, and a special visit from Santa from 4-6pm!
Starlight Cookie Stroll – December 18, 2025
Experience the magic of the Holiday Season as the city comes alive with twinkling Christmas lights and enchanting window displays. Take a leisurely stroll through the streets adorned with breathtaking lights and Holiday decorations. But that’s not all! As you wander through the illuminated streets, cast your vote for the “People’s Choice” (your favorite) window display. You’ll pick up your map of participating businesses at Main Street Winter Haven’s office at 5:30 pm.
Winter Spectacular at Grove Roots – December 19, 2025
Enjoy a winter wonderland at Grove Roots Brewing Co., complete with snow machines, sparkling Christmas lights, arts and crafts, three food trucks, cookie decorating, beer releases, AND Santa Claus!
Wrap Up the Holidays – December 20, 2025
Visit Downtown Winter Haven for a festive day of shopping and holiday cheer on December 21st! Explore an array of local downtown businesses offering special deals and unique finds. From boutique clothing to specialty gifts, there’s something for everyone on your list. Embrace the warmth of the community as you stroll through the decorated streets, and visit shops & restaurants.
FREE gift wrapping will be available at the Main Street Winter Haven office from 10am-2pm for anyone who shops in Downtown Winter Haven. Let us help you wrap up your holiday! This is your chance to support local businesses while enjoying the magic of the holidays. Mark your calendars for December 20th and be part of this holiday celebration in Downtown Winter Haven!
A Charlie Brown Ski Show – December 20, 2025
Visit Lake Silver in Winter Haven for a free ski show by the Cypress Gardens Water Ski team. Themed to a Charlie Brown Christmas, the pre-show starts at 3:15 and the main show is at 4:00pm.
