Come hear our local legislative delegation discuss the critical issues they addressed during session, provide updates on legislation impacting Central Florida, and share their insights on when and how this year’s budget may be resolved.
Winter Park Outlook | September 19, 2025 | 11:30 a.m. - 1:30 p.m.
Winter Park Outlook is our annual regional issues summit exploring factors that affect economic development. Expert keynote speakers have addressed topics such as transportation, attainable housing, parking mandates and other challenges facing our region and our business community.
Autumn Art Festival | October 11 & 12, 2025 | 9:00 a.m. - 5:00 p.m.
The Winter Park Autumn Art Festival is the only juried fine arts festival exclusively featuring Florida artists. Held the second weekend in October in Central Park along Park Avenue in Downtown Winter Park, the festival presents original artwork in a wide range of mediums, live music on the Central Park stage, a children's art workshop, a beer garden and food vendors. Admission is free.
Best of Winter Park | October 28, 2025 | 5:00 p.m. - 7:00 p.m.
Best of Winter Park is an annual competition and celebration that recognizes the extraordinary offerings of our member businesses. The community votes on their favorite member businesses across 50 categories. The winners and finalists are highlighted at the celebration.
Winter on the Avenue | December 5, 2025 | 5:00 p.m. - 9:00 p.m.
Held in Central Park, along Park Avenue, Winter On The Avenue is a kickoff to the holiday season. Come out for our annual tree-lighting ceremony, Chanukah menorah lighting ceremony, strolling carolers, s'mores, snow slides, the announcement of holiday art contest winners, children's choirs, Popcorn Flicks in the park, and, of course, Santa and Mrs. Claus. Admission is free.Â
Leadership Winter Park Pancake Breakfast | December 6, 2025
Enjoy a hot breakfast before or during the annual Christmas Parade. Our Leadership Winter Park alumni and current class host this annual fundraiser every year in Central Park. The breakfast includes pancakes, sausage, toppings and a beverage. Proceeds support leadership development scholarships for students and adults as well as education-focused nonprofits.
Christmas Parade | December 6, 2025 | 9:00 a.m. - 10:30 a.m.
The Winter Park Chamber of Commerce is proud to host the oldest continuous holiday parade in Central Florida. Over 80 organizations participate, including marching bands, local police and fire departments, scouting groups, elected dignitaries and, of course, Santa Claus.
Cheers to You! | Returning 2026
Cheers to You! are our annual Membership Awards that pay tribute to the members and volunteers who make the Winter Park Chamber and the Winter Park community exceptional. The Lydia Gardner Citizen of the Year is annually named and recognized at this event.
State of the City | Returning 2026
Our annual State of the City luncheon features an address from the Chamber President/CEO. We will reflect on our achievements and prepare for the future opportunities and challenges facing our city.
Meet the Candidates | Returning 2026
Meet The Candidates is a gathering of voters and candidates at the Center for Health & Wellbeing. Attendees will have the opportunity to connect directly with candidates. Attendees will enjoy light refreshments and have the opportunity to vote in a straw poll.
Women of Influence | April 23, 2025 | 11:30 a.m. - 1:30 p.m.
Women of Influence is our annual luncheon honoring the trailblazing female leaders within our community who inspire us, guide us and shape our community. We recognize the Woman of Influence and the Woman of Influence Lifetime Achievement Award honoree and celebrate the graduates of Relaunch: Career Reentry for Professional Women.
Questions? Contact our Events Manager Gabbi Formosa at gformosa@winterpark.org or 407-643-1698.
Sponsor an Event
Each event has associated sponsorship opportunities curated to help you reach your targeted audience and support your business through recurring recognition, brand cohesion and community engagement. Explore our Sponsor Guide to find the right opportunity for you.
Questions? Contact our Senior Director of Strategic Partnerships Stacey Cox at scox@winterpark.org or 407-599-3646.