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Road Trip: Madison, Green Bay, and Washington Island

Updated on July 21, 2024

Lake Michigan

The view of the Lake from our would-be pirate ship
The view of the Lake from our would-be pirate ship | Source

Getting there

In the fall of 2009, I had the experience to drive from my home town of Clearwater, Florida to the very tip of Door County, Wisconsin, and back. The trip up was just intense, non-stop driving, stopping only for gas, food, and the call of nature. We left from a sweltering Burger King parking lot in central Florida around 11 am, so by 8 that night the view had changed to inky blackness. There was nothing to see until dawn the next day as we bypassed west of Chicago on the Kennedy Expressway.


After the Chicago skyline faded off behind us, we didn't see anything but fields, punctuated by the occasional grain or corn silo. The landscape was changing to beautiful colors of browns and reds as the leaves fell in late November. There was a chill to the air but there had been nothing significant yet that year as far as cold fronts. It wasn't until we got to the edges of the Door Peninsula in Wisconsin that we began to see the landscape change to more forested and rolling areas.



Rolling Streets of Door County

Door County
Door County | Source

Door County


My roommate Tripp needed a driver to help him get a truck back from Wisconsin. He and his father were purchasing a 60ft steel-hulled ferry boat from Washington Island Ferry Services in Northern Door County, Wisconsin. Their intentions were to sail the vessel down the Mississippi River to Mobile, Alabama, cross the Gulf of Mexico closer to our area and dock at Tarpon Springs. At the dry-dock, the ship would be stripped, cleaned, and retro-fitted into a mock pirate ship and sailed to the Cayman Islands to do tours for tourists and their families. According to Coast Guard regulations, a ship that big is not allowed to sail without an operational rescue craft on-board in case of a capsize. That is where me and the truck come in. Tripp and I were to drive a Nissan Xterra with a 10ft Zodiak raft from Florida up to the ferry on Washington Island, unload it and mount it inside the newly acquired vessel. At that point I would drive the truck back home to Clearwater, Florida.


Crossing the bridge at Sturgeon Bay offers drivers an amazing view of Green Bay to the West and Lake Michigan to the East. Ahead lay the sleepy towns of Egg Harbor, Ephraim, and Sister Bay that celebrate the fall with festivals and street parades that I was detoured around for a while on my return trip. As you travel North up the peninsula towards the end at Gil's Rock and the ferry service, the road suddenly opens up in front of you and displays a stunning panoramic of the town below, then you peak the hill and start down towards it. The colors and hills are like a thick quilt spread over the town as it lays down to get comfortable for winter.

Lake Michigan at Dusk

I took this from the rear of the ferry going from Wisconsin to Washington Island.
I took this from the rear of the ferry going from Wisconsin to Washington Island. | Source

Washington Island and the Ferry

At the northern tip of the peninsula is Gil's Rock, a series of rock-wall jetties that protect the ferry at port. Cars line up in two rows of 6 or so, drivers buy a ticket from the small booth, and wait for the boat. In November it was windy and cold but we had been in the truck for something like 25 hours solid and we were ready to face the elements for a little stretching and walking.

The ferry finally comes slowly in and maneuvers itself around to allow the vehicles smooth entry. The ship is made fast to the tire-lined concrete seawall and the hydraulic door comes down. The cars are filed in by guides and the boat reverses the docking procedures, taking to the circuitous route through historically famous shipwreck territory known as Porte des Morts, Death's Door.

If you make it through these treacherous waters (you will), past small foggy islands with picture-perfect lighthouses high on craggy cliffs, seven miles from the start is Washington Island. The town is extremely small, thriving on tourism due to a poor mining industry. The location cannot be beaten, and the passage through the Door County area is worth the trip alone.

I can remember wondering why the grim-faced owner of the ferry service wasn't smiling when he received $160,000 cash and a handshake from Tripp and his father. I was told later that the man owed almost a million bucks on dual boats that could transfer cars, people, and supplies from the Wisconsin mainland to Washington Island going in each direction regularly throughout the day. I see that the price of the old ferry boat we were buying was but a drop in the bucket that was the old man's problems.

When the purchase of the ship was concluded we stocked it heavily, making constant trips to the tiny island store. Before falling asleep in my hotel room that night, I considered the drive home and some stops I wanted to make along the way. The result was 33 hours of old and new friends, great food, better music, and lots of memories from a glimpse into the nation I am proud to call home.

She Became A Pirate Ship

60ft steel-hulled ferry that has since become a Cayman pirate ship.
60ft steel-hulled ferry that has since become a Cayman pirate ship. | Source

The Bluffs at Fish Creek

Source

A Brief Look at Green Bay and Madison, WI

When all of the shuffling and paperwork was finished on Washington Island, I took my time driving through some of the most beautiful areas I had ever seen. It turns out Door County in the Fall is a much sought-after experience, though I had missed the brunt of the tourists.


I made my way south towards Green Bay throughout the morning hours, getting a speeding ticket from a friendly state trooper on my way, of course. As I entered the Green Bay city limits I looked for radio stations and found a Packer's home game was in progress. The city soon proved to be up and about with what must be the only excitement the bleak city gets. Nothing personal to Green Bay as a population, the people were awesome and friendly; would give you the shirt off their back if you asked, not that you would. The city itself had that rusty, tired industrial look that always reminds me of Milwaukee. It is because I am a Florida native, and not used to the effects of snow and salt on everything. I got a call from a former, but then-current, girlfriend saying our mutual friend was tail-gaiting at Lambeau field.


It wasn't hard to find my friend in this city thronged with fans. Five minutes later Brian walked drunk right into the truck I was driving while I was sitting in a parking lot describing what I was looking at. It wasn't until he turned to apologize to me did the recognition spark in his eyes.

Packer's Stadium in Green Bay

Lambeau Field
Lambeau Field | Source

Old Fashioned in Mad-Town

My friend's group was tailgating in a parking lot across the street from the stadium. From the back of someone's truck a small portable grill was cooking spicy Italian sausage links to go on the hoagie buns teasing nearby. Onions and peppers were already grilled and waiting. Among immature chides to do otherwise, I maintained a responsible refusal to get hammered.

We stayed late at the game so I followed my friend back to Madison two hours away from Green Bay where he was staying in his parent's guest house while he was in town. There was an air mattress all set up and ready for me when we got to town. His thoughtful mother was a blessing after the long day I had. Brian insisted that the trip to Mad-Town wouldn't be complete without having an Old Fashioned at a nearby bar. I liked it, and would definitely have another anytime.

Madison, WI Capitol Building

Source

The Saga Continues

Following me on my trip south from Wisconsin as I hit Chicago, Indianapolis, Louisville, Nashville, Atlanta, and finally Tampa Bay, a.k.a. Home. The next legs coming soon.

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