There’s something different about how Winter Park welcomes the season. It doesn’t shout or overwhelm. It just feels right. On November 30, from 3:30 PM to 5:00 PM, the heart of the Winter Park Village glows a little brighter. Locals and visitors gather for the Holiday Tree Lighting, a short, heartfelt tradition that marks the start of the town’s winter magic.
This free event fits perfectly into your weekend plans. You’ll hear live holiday music from The Beverly Belles, smell fresh cookies being passed around, sip hot chocolate while walking through the decorated village, and—yes—wait for Santa to appear. You don’t need a ticket or reservation. Just bring your coat, your people, and a little excitement for the season ahead.
The Moment the Lights Switch On
The tree stands tall at the center of the village. As the sun dips behind the mountains, the lights flicker on and the crowd quiets. You’ll hear kids react with excitement, friends laugh as they point to ornaments, and the Belles close their song just as the tree reaches its full glow.
It’s not a huge production, but that’s what makes it special. You’re not lost in a sea of strangers. You’re part of something real. Families take photos in front of the lit tree. Couples take a moment to just be still. Even those visiting for the first time find themselves smiling at how personal the night feels.
After the lights come on, you can stroll the village and enjoy the rest of the evening. Grab a warm bite from one of the local restaurants or browse nearby shops without the usual holiday pressure. It’s a calm, easy way to start December.
Why Stay Overnight Nearby
If you’re thinking of heading back to the city after, pause. This is the kind of evening that’s better when it ends slowly. Let the cold air linger on your cheeks a little longer. Let the glow of the tree reflect on your evening, not your rearview mirror.
The Jabberwocky, just minutes away in Winter Park, gives you the kind of night that matches the tone of the event. It’s quiet, personal, and made for moments like this. You walk into a space that’s already warm. The fireplace is waiting. Your holiday photos from the tree lighting don’t get buried—they’re reviewed together, with a blanket and a cup of something hot in hand.
A Thoughtful Winter Weekend
You can make this more than a one-night trip. If you arrive early, the slopes are open. Spend your morning skiing, then change into something cozy and head into the village for the tree lighting. If you’re traveling with family, there’s room to unwind and reconnect at The Jabberwocky. If you’re visiting solo or with a partner, you can treat yourself to a peaceful mountain stay without any hassle.
The weekend after Thanksgiving can be hectic elsewhere. But not here. Here, the trees are frosted naturally, the people are friendly, and the start of the holidays comes without pressure. Just music, lights, and a tree that reminds you to slow down and enjoy what’s here.
Make This the Start of Something Better
There’s always another party. Another city light show. Another parade. But Winter Park offers something different—a space to settle into the season, not speed through it. When the tree lights up on November 30, let it light up more than your evening. Let it light up your plans, your mood, and your year’s close.
Make The Jabberwocky your base for that. It’s not a hotel. It’s not a resort. It’s a real home in the mountains, just for you and the people you want to spend time with.
Book your stay at The Jabberwocky and give this holiday tradition the time it deserves. Let the season start here, with meaning.
