Sidewalk of Doom, meet the Sidewalk to Nowhere 

By Skip Foster, Red Tape Florida 

Just a couple of hundred yards north of Midtown Reader — where a recent Red Tape Florida series told the story of a sad plot of grass which serves as a burial ground to common sense — you’ll find a different monument to bureaucratic ineptitude. 

It’s the Sidewalk to Nowhere. 

Tallahassee readers have probably seen it many times, but never really noticed it. 

It’s near the southwest corner of Gadsden Street and 7th Avenue, adjacent to the building that holds Brass Tap and Orange Theory. 

The sidewalk is incredibly short … just 50 feet. It’s the kind of feature that just becomes a part of a driver’s peripheral vision. 

And yet, as you are about to find out, it’s another one of the hidden monuments in Tallahassee. Markers to incompetence, business-unfriendliness and, of course, red tape. 

A sidewalk on the wild side 

Here is a link to the exact stretch of sidewalk we are talking about. 

 You’ll notice a few things: 

1) Other than this 50-foot stretch, there is no sidewalk anywhere in the vicinity on the west side of Gadsden. If you head south, you’ll see this sidewalk-free zone continues all the way to Johnson Street – about a half mile away. 

2) To the north, the sidewalk dead ends into a power pole (a little hard to see since the satellite is shooting straight down on it, but if you drive by, you’ll see). If Harry Potter had a Tallahassee portal to Hogwarts, this might be it. 

3) There is no crossing lane or any other reason for this sidewalk to be here. 

So, why is it here? 

Because 10 years ago, the City’s director of public works told Roger Osborne, the landowner, that it had to be included or he couldn’t build on his land. 

The lot in question 

Roger Osborne’s adult life started Tallahassee in the 1970s and he returned here a couple decades later and has never left. He is a C.P.A. by trade, who got his Master’s in accounting from Georgia State after getting his M.B.A from FSU in the 1970s. 

Most recently he has worked in commercial real estate, perhaps most significantly as the developer of the VA outpatient clinic in Tallahassee. 

Around 2003, he and partners wanted to build townhomes on the property in Midtown, but that fell through and the partnership dissolved leaving him the sole owner. About 10 years later, he decided it was time to develop the lot, but shifted to a retail plan. 

He went through the always-arduous permitting process and was on the verge of getting his development permit issued when the City public works director intervened. “I want a sidewalk on Gadsden Street,” the official demanded. 

Initially, Osborne reminded the City that they had proposed a “fee in lieu of” for the sidewalk. That essentially meant Osborne would pay a fee since a sidewalk wasn’t required. It was an offer which Osborne accepted. 

But, even though all the engineering plans were complete, the then-director of public works insisted that a sidewalk be added. He argued that the City was moving toward a more walkable planning model and, even if this was the only small stretch of sidewalk in the area, there could be more connected to it … “some day.” 

The City director made it clear – the project wouldn’t start until Osborne agreed to build a sidewalk. 

In other words, the City withdrew its offer at the last minute. 

And, “some day” still hasn’t come. 

Much more (expense) to the story 

Unlike the Midtown Reader Sidewalk of Doom, the Sidewalk to Nowhere didn’t actually cost Osborne more to build than the fee he was going to pay anyway. 

But that doesn’t mean it wasn’t expensive in other ways. 

The expense in this matter was this: Building the sidewalk shifted the entire project – from Gadsden to Thomasville Road by — 10 feet. 

Do you know what it costs to redesign and reengineer a project of this magnitude by 10 feet? 

Osborne does. He calculates the shift cost him around $90,000 — in additional fees to engineers and architects to reposition the building and added interest.  That also includes the added time – months and months when he could have been receiving lease revenue (and when tenants could have been hiring employees and growing their own businesses). 

In the business world, time is money. In the bureaucracy, time is someone else’s problem. 

This was the original design of the building, which had to be simplified when the “Sidewalk To Nowhere” shifted the building footprint too close to power lines. 

An even uglier reality 

Then, the most painful irony. 

That 10 feet brought the building – and specifically, a beautiful design element of the edifice – too close to overhanging powerlines. Osborne had to scrap the artistic façade, and go with a much plainer design. 

In other words, as it turned out, the “placemaking” mentality that led to a Sidewalk To Nowhere actually made the area less visually appealing than it would have been. 

Of course, Osborne encountered the other usual array of City silliness. Because the lost feature had a somewhat Mediterranean feel to it, he wanted to plant expensive Italian Cypress trees to line the property. 

The City said no – they aren’t on our approved tree list. 

Later they came back and said he could pay $2,500 for a special variance. 

Chew on that logic a second: You can pay us money for the right to pay more money to have something nicer on land … that you own. 

Osborne was also required to do an archeological dig, for reasons never fully explained to him. The firm hired to do it was so embarrassed it was being required that they barely charged him anything. 

Why is a 10-year-old story important? 

Two reasons: 

1) It shows that the culture of Tallahassee permitting dysfunction has been around a long, long time and will take a major effort to fix. 

2) The same logic being used today to drive decision making – “placemaking,” pedestrian-friendly, sidewalks over parking – was being used 10 years ago. 

Italian Cypress trees. Too fancy to be on the City’s list of trees — but the City still charged $2,500 for a variance. 

Guess what? People are still choosing to, almost always, drive cars. 

You may not like that, you may not want that. But it’s the reality of the world and pushing policies misaligned with how people actually travel ultimately costs money for businesses and that ultimately costs jobs. 

And Red Tape Florida readers are well aware that this isn’t a community that can afford to lose jobs. 

After all, more economic stagnation in this market and we will be a Community to Nowhere. 


April 8, 2026
Skip Foster, Red Tape Florida