Cultivating Connection: The Chamber Events That Inspire Winter Park
October 21, 2025
The Winter Park Chamber of Commerce curates a dynamic calendar of Signature Events that embody the city’s spirit of leadership, collaboration and community pride. Each gathering tells a story of innovation, civic engagement and celebration. Together, these events form a rhythm of connection that unites residents, businesses, and leaders throughout the year.
Cheers to You!
The year begins with Cheers to You!, an evening dedicated to honoring the members and volunteers who make our Chamber -- and our community -- truly exceptional. This annual Membership Awards Dinner shines a spotlight on those who go above and beyond in service, leadership and community spirit.
A highlight of the night is the presentation of the Lydia Gardner Citizen of the Year Award, recognizing an individual whose contributions have made a lasting, positive impact on Winter Park. Surrounded by friends, colleagues and community leaders, attendees enjoy an evening of celebration, gratitude and inspiration as we raise a glass to the people who help make Winter Park a vibrant place to live, work and connect.
State of the Winter Park
Following this festive kickoff, State of the Winter Park offers an in-depth look at the city’s progress and future priorities. During this luncheon, Chamber leadership highlights achievements, ongoing projects, and emerging opportunities that shape Winter Park’s growth. The event fosters transparency and shared vision, inspiring attendees to contribute to the city’s continued success. By bringing together business leaders, residents and officials, the Chamber ensures the community remains informed, connected, and forward-focused.
Meet the Candidates
Meet the Candidates creates an important platform for civic engagement by connecting residents with those seeking public office. The event provides a welcoming space for open conversation, allowing attendees to hear directly from candidates, ask questions, and participate in a straw poll. This face-to-face interaction encourages accountability and helps voters make informed decisions. The Chamber’s commitment to this event demonstrates its dedication to strengthening local democracy and promoting active citizenship.
Women of Influence
In the spring, the Chamber honors female leadership through Women of Influence, a signature luncheon that celebrates women making significant contributions to Winter Park’s civic and business communities. The event highlights honorees whose achievements in leadership, philanthropy, and service inspire others to pursue excellence. It also recognizes graduates of Relaunch: Career Reentry for Professional Women, a program supporting professional women reentering the workforce. Together, these stories of perseverance and impact create an atmosphere of mentorship, empowerment, and celebration.
Legislative Update
The annual Legislative Update connects the community directly with policymakers. During this informative event, state and local legislators share updates on the most recent legislative session, discuss key issues, and outline how new policies will affect businesses and residents. Attendees gain a deeper understanding of current legislation and the opportunity to voice their perspectives. This exchange fosters cooperation between decision-makers and the community, ensuring Winter Park remains informed and engaged in shaping its future.
Winter Park Outlook
As the year continues, Winter Park Outlook provides an opportunity for strategic discussion about the city’s economic landscape. Industry leaders, entrepreneurs, and community members gather to examine topics such as development, infrastructure, and workforce trends. Through thoughtful presentations and panel discussions, attendees gain insights into the forces driving Winter Park’s growth. The Chamber uses this event to champion innovation and spark collaboration, aligning efforts across sectors to build a thriving local economy.
Autumn Art Festival
Each fall, the Chamber hosts one of Winter Park’s most anticipated traditions, the Autumn Art Festival. This juried fine arts showcase features the work of talented Florida artists in painting, sculpture, photography, and more. The event transforms Central Park into an open-air gallery filled with live music, food vendors, and family activities. More than an art show, it is a celebration of creativity and community that reflects Winter Park’s appreciation for culture and craftsmanship.
Best of Winter Park
The Best of Winter Park competition and awards celebration honor outstanding local businesses and organizations that exemplify excellence and community spirit. Nominated and voted on by the community, the event highlights achievements across a range of industries. Attendees gather to celebrate innovation, hard work and success -- qualities that define Winter Park’s entrepreneurial spirit. The evening’s atmosphere is one of pride, camaraderie and celebration, underscoring the vital role small businesses play in sustaining the city’s vibrancy.
Winter on the Avenue
As the holidays approach, Winter on the Avenue lights up downtown with festive charm. Families and friends fill Park Avenue to experience the city’s tree lighting, Chanukah menorah lighting ceremony, carolers, and holiday treats. Snow slides, s’mores, and twinkling lights create a magical evening for residents of all ages. The Chamber’s commitment to inclusivity shines through this event, which celebrates togetherness and joy in the heart of Winter Park.
Leadership Winter Park Pancake Breakfast
The next morning, the Leadership Winter Park Pancake Breakfast brings the community together for a cheerful morning meal that supports scholarships and leadership programs. Hosted by alumni of the Chamber’s Leadership Winter Park program, the breakfast pairs warmth and purpose, fueling both bodies and spirits before the day’s festivities. It’s a reminder that community service can be as joyful as it is impactful.
Ye Olde Hometown Christmas Parade
The year concludes with the beloved Winter Park Christmas Parade, the longest-running holiday parade in Central Florida. Marching bands, community organizations and festive floats fill Park Avenue with laughter and holiday music. Families line the streets to wave and celebrate as Santa and Mrs. Claus make their grand appearance. This cherished tradition embodies the unity, creativity and pride that define Winter Park year after year.
The Winter Park Chamber of Commerce’s Signature Events do more than fill a calendar, they cultivate connection. Each celebration, discussion, and ceremony strengthens the bonds between neighbors, businesses and civic leaders. Together, these events tell the story of a community that leads with purpose, celebrates with gratitude, and grows through collaboration. In Winter Park, connection isn’t just encouraged, it’s inspired.