In October 2014 I had the privilege of participating in a Urban Land Institute panel focusing on Winter Park.
ULI’s TAP program (Technical Assistance Program) brings outside help to communities seeking advice on how to seize an opportunity or address a vexing issue in their city.
It was a great honor to be chosen to participate, because I have long admired Winter Park and I’m a big fan of Bob Rhodes, who is a legend in Florida.

Bob was Chair for the Winter Park TAP and shortly after the exercise he was honored with a much deserved lifetime achievement award from Leadership Florida.

Led by Bob, the panel produced a document aimed at framing some issues that Winter Park was facing relating to downtown development and offering them some solutions to consider.
So it was interesting for me to return to the city two years later to see what was happening downtown.
We spent a day strolling, dining and shopping on Park Avenue over the holiday break.
It was a beautiful day and the street was bustling.
Park Avenue has a similar scale to Atlantic Avenue, mostly two and three story buildings. Winter Park has some distinct architecture and it’s streetscape is immaculate.
Gorgeous planters, attractive signage, cool little side streets and a lineal park that runs alongside Park Ave gives the city remarkable charm.
While Atlantic Avenue is restaurant heavy, Park Avenue is dominated by retail.
There are a fair amount of chain stores and franchises ranging from Gap for Kids and Restoration Hardware to Starbucks and Burger Fi.
But there’s also a decent number of independents—the feel is decidedly upscale but not pretentious.
It’s a vibrant street and just feels good.
What makes Winter Park interesting is it’s able to succeed as a counter to much larger Orlando which sits (looms) next door.
Orlando’s downtown has come a long way in recent years under the leadership of Mayor Buddy Dyer.

As a result, Orlando is now much more than just theme parks and vacation villas.
Still, Winter Park still feels like an oasis in Central Florida.

The city wants to keep that charm and I think it will. ULI was brought to the city as a result of a strong desire for Winter Park to remain special in a sea of sameness, sprawl and traffic.

We also visited Celebration which is known for its new urban layout and variety of architectural elevations.
Now 20 years old, Celebration looks better with a little age on it. A former Leadership Florida classmate was one of the developers of the landmark project–which has received a huge amount of press over the years– so I had some insight into the thinking that Disney was trying to achieve in Celebration. The goal was to replicate some of the best features of American town planning before cookie cutter design began to proliferate. Critics called it a “Stepford” community, almost too perfect to feel warm and authentic.
I remember visiting some years ago and it felt much more faux than it does today. It has aged well and even my kids–not usually attuned to such things–noticed how different the neighborhoods were in terms of design.
Celebration and Winter Park stick out in a region that is suffering from an acute case of sprawl with all of its attendant illnesses including choking traffic and soulless sameness.
I wish there were more places like Winter Park and our own Delray Beach.
I sense that there’s a large market of people who want a walkable lifestyle, distinct architecture, interesting shopping choices and good local restaurants. Throw in attractive open spaces and large doses of culture and educational opportunities and you have a recipe for enduring success. You also have a recipe for high housing costs, which price many people who would enjoy and contribute to these places out of the market. One answer is density–done well of course–which adds supply and is also better for the environment. But the “D” word is often a third rail in local politics and public officials unwilling to do the hard work of engaging the community in an education effort often abandon the types of development patterns that people long for and create value well beyond a bottom line.
Will cities like Winter Park and Delray change?
No doubt.
But as long as they keep their “bones” and scale intact they will continue to succeed.
We just need more communities to follow their lead. And more public officials willing to push for quality of design rather than simply judging projects based on numbers.