Park Avenue District

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Winter Park, FL
Park Avenue District

The mission is to enhance the Avenue through historical preservation, small business support
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08/03/2026

"There's nowhere else I'd rather live in the world."
When someone who has spent years investing in our community says those words, they carry a little extra meaning.
We sat down with Andrea Massey-Farrell to talk about what makes Holidays on Park so special, and why preserving these traditions matters.

Her message is simple:
"I wish more people would get involved to help ensure that the community thrives for generations to come."
We couldn't agree more.

Holidays on Park is more than a tree lighting or a parade. It's a season that brings neighbors together, welcomes visitors, supports our local businesses, and creates memories families carry with them for a lifetime.

As we continue our Become Part of the Magic campaign, we're inviting our entire community to be part of keeping these traditions alive.

🎄 Become a sponsor or holiday supporter by making a donation.
🎄 Become a Park Avenue District member.
🎄 Share this post with someone you know has a favorite Park Avenue holiday memory.
🎄 Tell us in the comments: What's your favorite Holidays on Park tradition?

Because the places we treasure don't stay that way by chance. They thrive because people choose to care.

For more information about sponsorship opportunities contact Allison Chandler, Executive Director.
Email: [email protected]
Visit parkavenuedistrict.com/holidaysonpark to contribute to the Magic.

Thank you to Andrea and the Massey family for all they do to give back to Winter Park and central Florida.

08/01/2026

While most of Central Florida is wrapping up their summer, at Park Avenue District we're already looking ahead to the holidays. Become Part of the Magic campaign invites sponsors, businesses, and the community to help create the holiday experiences that make the Park Avenue District a cherished seasonal destination.

Thanks to the City of Winter Park’s $70,000 matching contribution, the Become Part of the Magic campaign is off to a strong start.

The campaign marks the official opening of our 2026 holiday sponsorship initiative, with community support helping fund the lights, décor, family experiences, and festive touches that transform Park Avenue each holiday season. This campaign reflects Park Avenue District's broader mission to preserve the character, cultivate the experience, and steward the future of one of Florida's most iconic Main Street districts.

Come along side the Park Avenue District! We invite YOU to help keep the magic of Holidays on Park alive for generations to come.

🎄 Become a sponsor.
🎄 Become a Park Avenue District member.
🎄 Share this post with someone you know has a favorite Park Avenue holiday memory.
🎄 Tell us in the comments: What's your favorite Holidays on Park tradition?

For more information about sponsorship opportunities contact Allison Chandler, Executive Director.
Email: [email protected]

07/28/2026

Beginning November 27, Holidays on Park, in partnership with the City of Winter Park, will
once again fill Park Avenue with dazzling lights, the beloved Holiday Carousel, festive
displays, family experiences, and the warmth and charm that have become synonymous
with the holidays in Winter Park.
And, you can expect all our merchants to join the fun and welcome in the season.

This year, is getting ready to spread plenty of holiday cheer with their festive Girls' Night Out events, and they're just one of the many businesses that help make Park Avenue feel like home during the holidays.

Throughout the fall, we'll be introducing you to the incredible merchants who help transform Park Avenue into a place where locals gather, visitors make memories, and traditions are born.

Our Become Part of the Magic campaign invites our entire community to help keep these traditions alive.

🎄 Become a Park Avenue District member.
🎄 Become a holiday sponsor.
🎄 Share this reel with someone who loves Christmas on Park Avenue.
🎄 Tell us in the comments: Which Park Avenue shop is part of your holiday tradition?

Holidays on Park belongs to all of us and together, we can ensure the magic continues for generations to come!

07/27/2026

Each year, Park Avenue becomes a gathering place where nearly 400,000 locals and visitors from around the world celebrate the season beneath twinkling lights, enjoy the beloved holiday carousel, and create traditions that span generations. While the experience feels effortless, it is made possible through months of planning, a strong partnership with the City of Winter Park, and the generosity of sponsors, businesses, and community supporters who believe these traditions are worth preserving.

Come along side the Park Avenue District! We invite YOU to help keep the magic of Holidays on Park alive for generations to come.

🎄 Become a sponsor.
🎄 Become a Park Avenue District member.
🎄 Share this reel with someone you know has a favorite Park Avenue holiday memory.
🎄 Tell us in the comments: What's your favorite Christmas on Park Avenue tradition?

For more information about sponsorship opportunities contact Allison Chandler, Executive Director.
Email: [email protected]

07/25/2026

We stopped people on The Avenue (yes, in July) and asked them about what it's like to experience the holidays in the Park Avenue District.

Their answers were about the lights and decorations. But they also spoke about family traditions.

Making the same memories, year after year. Picnics in the Park. Listening to live music. Strolling The Avenue with the family.
That's the magic of Holidays on Park.

Each holiday season, Park Avenue District transforms our beloved main street into a place where generations gather, traditions continue, and new memories are made. It's a celebration that belongs to our entire community — but it only happens because businesses, sponsors, members, and neighbors choose to make it possible.

As we kick off Christmas in July, we're inviting YOU to help us keep the tradition alive.

🎄 Become a sponsor.
🎄 Become a Park Avenue District member.
🎄 Share this reel with someone you know has a favorite Park Avenue holiday memory.
🎄 Tell us in the comments: What's your favorite Christmas on Park Avenue tradition?

Together, we can ensure the magic of lights and carousels continues for generations to come!
For more information about sponsorship opportunities contact Allison Chandler, Executive Director.
Email: [email protected]

https://givebutter.com/holidays-on-park-ckqsd1?gba_donor_ref=vFk55h1aF5kd2mn2

07/01/2026

🇺🇸 Celebrate Independence Week on Park Avenue! 🇺🇸

Join us as Winter Park commemorates America’s 250th birthday with a week full of music, history, family fun, and patriotic pride.

🎶 July 1 – Enjoy the 250 Great American Big Band Concert in Central Park at 7:30 p.m.

🎆 July 3 – Celebrate at the 31st Annual 4th of July Celebration in Central Park from 6–9 p.m. with performances by the Bach Festival Brass Ensemble and Choir.

🏛️ July 3–5 – Visit the Morse Museum with FREE admission and enjoy live music while exploring incredible American treasures.

📜 Explore the America 250 Exhibit at the Winter Park History Museum through July 18.

🏪 As you stroll Park Avenue, don’t miss the Downtown Window Decorating Contest, where local businesses are showcasing patriotic displays in honor of America’s 250th anniversary.

Whether you’re enjoying live music, exploring our museums, shopping and dining along the Avenue, or celebrating with family and friends, there’s no better place to experience the spirit of Independence Week than Park Avenue.

🇺🇸 We can’t wait to celebrate with you!

05/25/2026

Today, as we enjoy time with family, friends, and community, we pause to remember that Memorial Day is about something far greater. 🇺🇸

We honor the brave men and women who gave their lives in service to our country and recognize the families who continue to carry that sacrifice every day. Their courage and selflessness are the reason we are able to gather freely in the places and communities we love.

Here in the Park Avenue District, we are grateful for those who served and sacrificed for our nation and for the values that bring communities like ours together.

From all of us at the Park Avenue District, thank you to our fallen heroes. We remember you today and always. ❤️🤍💙

04/30/2026

A special evening with Club 1882

A FULL HOUSE of Club 1882 members enjoyed a private after-hours tour of the incredible Charles Hosmer Morse Museum, followed by a beautiful cocktail reception at Boca. It was the perfect way to experience the art, history, and hospitality that make Winter Park and the Park Avenue District so special.

Thank you to everyone who joined us for this memorable night — and to our wonderful partners who helped make it possible. We love creating experiences that bring our community together in unique and meaningful ways.

CommunityConnection

04/20/2026

🎨 Easels on the Ave. Wine in hand. A perfect Wednesday night on Park Avenue! 🍷✨

Join us Wednesday, April 22 from 5–8 PM for the annual Paint-In on Park Ave, presented in partnership with and the . Stroll the Avenue as talented plein air artists paint live outside your favorite shops while you enjoy wine, bites, and a beautiful spring evening in Winter Park.

✨ More stops than ever this year & 2 Raffle Baskets
✨ Local artists painting throughout the district
✨ Wine, shopping, and a night out with art lovers

We sold out last year, so grab your tickets early!

See you on the Ave with:

Charyli

winterpark

Plus a few friends popping up to make the night even sweeter:

03/31/2026

🐰✨ WOW—YOU DID THAT! ✨🐰

We are so excited to share that the Bunny Hop on Park Avenue SOLD OUT in the first day! 🤍 Because of the incredible response, we’ve added an additional storytime at 2:00 PM at Writer’s Block Bookstore.

Spots are limited and will go fast (again 👀), so don’t wait!

👉 Register now — link in bio

We can’t wait to see you and your little bunnies hopping the Avenue! 🌸🐇

SpringEvents OrlandoFamilies

Address

110 Park Avenue North
Winter Park, FL
32789

Website

http://WWW.PARKAVENUEDISTRICT.COM/

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