Welcome to

Winterfest Volunteering!

Share the Cheer

The Winterfest celebration begins after Thanksgiving and runs through the weekend before New Year's Eve. We offer a free musical revue, visits with Santa, and several tours of downtown Pensacola. Throughout the rest of the year we raise funds through our parking and trolley services and build community awareness through outreach and community service.

Our Projects

Please refer to the following websites for information about the goals and missions of Winterfest and its associated activities (links open in a new window).

  1. The holiday event: http://pensacolawinterfest.org
  2. Trolley Theatre: http://trolleyrep.org
  3. Parking: http://parkpink.org
  4. Charter trolley services: http://fiveflagstrolley.com


Depending on your skills and availability, you may be assigned to one or more roles:

  • Acting (Red Trolley Theatre, Winterfest Event)
  • Hospitality (event planning, food service, Winterfest Event)
  • Office (accounting, bookkeeping, filing, marketing, reception)
  • Outreach (social media, writing, customer contact, fundraising)
  • Technical (computer, lighting, sound, construction)
  • Renovation (carpentry, metalworking)

In order to change starting time or cancel your appointment, please give us 24 hours notice at 435-0914. A second failure to appear without an excuse will result in reassignment.

Red Trolley Theatre

The Red Trolley Repertory Theatre is Pensacola's most original theatre company, producing mixed-media comedy, drama and hitory in our fully restored trolleys. There are two tours on weekends from May through September. One tour features the story of the alien invasion of Gulf Breeze while the other focuses on the history of pirates in Pensacola.

Trolley Services

Renovation on our trolleys is ongoing, and we can use your special skills. A list of current tasks is available at the office. We will work with your schedule to complete these tasks in a timely manner.

Office and Outreach

Community contact is an important part of Winterfest's efforts to build the best holiday celebration on the Gulf Coast. If you are skilled in organization, writing, computer work, or just love talking to people, we would love to have you in our office program. We have several exciting office tasks just waiting for the right person to come along.

The Main Event

Starting in late September, operations for the Winterfest celebration become our primary focus. We especially need technical work to enhance our performances and attractions. This year we will be operating a decorating program for Downtown Pensacola that will be a lot of work, but a lot of fun!

We look forward to working with you!