If a race is going to die before the starting gun ever gets fired, this is the burial ground filled with the most corpses. You've got to decide where to start the permitting process, and I generally prefer to start at the top, not where I'm told to start.
When I decided to resurrect the (now re-defunct) United States Triathlon Series in 1997 I chose to approach the city of Oceanside, California. This eventually became the scene of the California Ironman, and is now where the California Half-Ironman sits.
But in 1997 Oceanside had not had a triathlon in years, and was considered a dead venue. But I thought it had promise. The problem was convincing both the city and adjacent Camp Pendleton Marine Base to play ball. I had a strategy.
I called the largest area newspaper and asked for the reporter who covered the local Oceanside city politics beat. I called the reporter and asked, "Who's the city council member with the most ambition, who is good at building a consensus, and who's the real ass-kicker when it comes to getting things done."
"Oh, that's easy," said the reporter. "That's Carol McCauley."
So I scheduled an appointment with Councilman McCauley, and explained what I wanted to do. A week later I had a follow up meeting, and when I walked in the door there was the head of lifeguards, fire, city police, parks & rec, risk management, harbors & beaches, harbor police, special events, and public works. Simply put, I didn't have to make a sale to anyone else. Yes, these people had the power to make my life difficult, so I had to be very politically astute all along the way. But they all reported to the city council and the mayor.
My advice: do not ask where you're supposed to go in order to get a special event permit application. Go straight to the top. In my three years of putting on races in Oceanside, I don't believe I ever met the person at the window who takes special event permits.
Of course, it helps if you go in prepared. I started the process not only with the demographics of triathletes, and what I thought might represent a reasonable financial impact, but also unquantifiable elements, such as: "Solana Beach has a triathlon, so does La Jolla, Carlsbad, Pacific Beach. San Diego and Carlsbad have big marathons. Carlsbad has a huge 5000-meter road race. What does Oceanside have? Why can't Oceanside play? It's got better physical attributes than any of these cities. It and its citizens deserve their own first-class endurance event, don't they?"
Fast forward to today, Oceanside is the triathlon capital of San Diego. Carol McCauley had the vision to see that it could happen, and the willingness to stick her neck out. No special events functionary could make that call. You need a person with juice on your side. You need to find out who that person is, and make that one sale.
But what about Camp Pendleton? I didn't have to worry. Carol McCauley made the sale for me. No, I don't rank on that marine base. But the camp's municipal neighbor to the south certainly did.
Perhaps the person you need to make the sale to isn't a council member or mayor. Perhaps it's a county supervisor. Or the person in charge of the national forest through which most or all of the course goes. Or the local supervisor for the state highway service (CalTrans in California). You just need to determine which permit you need most badly, and which agency is tasked with the job of multi-use. In California we have lakes and reservoirs that must be used for recreation and special events, because that sort of multiple use was part of their original charter, when funds to build these reservoirs were appropriated. Putting on a triathlon is not a bother to them. It is a welcome to them. They have staff whose sole job is to go out and find people to use their bodies of water.
The trick is not to start at the bottom, where traveling up does represent work for those who must sign off on permits. It's to start at the top, where a successful special event represents a feather in one's cap.