Illustration of skaters on an outdoor plaza rink ringed with lights and a child holding a penguin skate aid (Fridays on the Plaza - Holiday Music Series)
Other Christmas Activities

Fridays on the Plaza - Holiday Music Series

2026 dates not announced yet. Details are from 2025.

Experience the charm of Downtown Winter Garden with live music every Friday night. The 'Fridays on the Plaza' series features a diverse range of musical acts throughout October and November, culminating in a special holiday music lineup throughout December, including festive carolers. It's the perfect way to enjoy a vibrant evening outdoors.

All ages FREE

Plan Your Visit

Last year

Neighborhood

Downtown Winter Garden

Featured Performers

  • Cam Gordon
  • Porchdogs
  • Crenshaw
  • Salted Vine
  • Old School Blues Band
  • Scott Davidson
  • Gentleman of Jazz
  • Sound Traveler Band
  • +3 more

Parking

Self-parking is available nearby and throughout downtown including along West Plant Street in front of the Theatre, a three-floor parking garage (160 S. Boyd St.), Downtown Pavilion parking lot, (104 S. Lakeview Ave.), City Hall parking lot (300 W. Plant St.), and other walkable parking options.

Location

Centennial Plaza Gazebo · Winter Garden, FL Get Directions

Local Insight & Ratings

Family Friendly

🎄 🎄 🎄 🎄 🎄 (5/5)

Best For

Families, couples, music lovers

Vibe

Relaxed, festive, community-oriented

Energy Level

Low

Photo Friendly

📷 📷 📷 📷 📷 (4/5)

Weather Sensitivity

High

Tips & Advice

  • Arrive early to secure a good spot, especially for the December holiday performances, as the Centennial Plaza Gazebo area can get crowded.
  • Check the monthly lineup in advance to see which musical acts are performing each Friday, as the genres vary.
  • Consider exploring the shops and restaurants in Downtown Winter Garden before or after the music to make a full evening of it.
  • Bring a comfortable chair or blanket for seating, as public seating may be limited, particularly during popular holiday performances.
  • This event is outdoors, so check the weather forecast and dress accordingly. Light jackets are often recommended for evening events.

Special Events & Promotions

  • December features a special holiday music lineup including 'Light Up Winter Garden', 'Dickens Carolers', and 'Mistletones'.

Links & Contact

Run by City of Winter Garden

Christmas Events Near Me is an independent guide, not the organizer of this event. For tickets, entries, vendor spots or questions, contact the organizer directly through their contact page.

Frequently Asked Questions

What kind of music can I expect?

The music varies weekly, featuring genres like acoustic covers, Cajun, Zydeco, folk, soft rock, blues, southern rock, and jazz. In December, the series includes special holiday-themed performances by carolers and festive bands.

Is there an admission fee?

No, admission to Fridays on the Plaza is completely free for all attendees.

Where is the event located?

The event takes place at the Centennial Plaza Gazebo in Downtown Winter Garden.

What are the event hours?

The music performances are held every Friday evening from 7:00 PM to 9:00 PM.

Are pets allowed at the event?

No, pets are not permitted at the Fridays on the Plaza event.

Browse Christmas in Winter Garden

Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.

Contributors & Updates

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