Final Preparations: Mount Desert Island, Wiscasset, and Freeport, Maine

Michael Orr
3 min readJun 17, 2021
A view of islands from Mount Desert Island in Acadia National Park, Maine, June 16, 2001
Mount Desert Island, Acadia National Park, Maine — June 16, 2001

Ahead of our departure, the first thing I needed to do was get to Maine and join Win in getting the van. I’d just returned from ten days in France and England with a group from my high school, so this was already a summer to rival all summers. Huge shoutout to my folks for facilitating that! But now I was almost on my own, flying from North Carolina to Portland International Jetport, where Win picked me up and drove us north to Freeport, where he and Wes grew up. From there we joined Win’s dad Frank for two days at the family cabin near Bar Harbor.

Small cabin with partial view of van on Mount Desert Island, Maine, June 16, 2001
Sheldon Family Cabin, Mount Desert Island, Maine — June 16, 2001

Along the way we stopped for a lobster dinner, as you do, and then spent the night on Mount Desert Island in Acadia National Park. Technically not part of the trip, but we’re going to count it anyway as the first of our national park adventures (I’m the writer here, after all), as we hiked up part of Cadillac Mountain. Along with providing us with the van and a cell phone (“Do not use this,” he told us), Frank’s final, incredible parting gift to us was a pass good for entry into any national park in the country. This not only saved us a ton of money over the course of our drive, but gave us clout when we hung it from the rear view mirror upon pulling into every park we visited, nodding knowingly to those manning the entry points.

All that was left was to drive back south toward Freeport to pick up the van. In the driveway of Frank’s house in Wiscasset, along the way back, we stripped the van of anything surplus to requirements, loaded coolers and blankets, and cleaned the thing.

Win admiring the van in Wiscasset, Maine, June 17, 2001
The Van, Wiscasset, Maine — June 17, 2001
Win’s reflection in the van’s front bumper, Wiscasset, Maine, June 17, 2001
The Van, Wiscasset, Maine — June 17, 2001

After a few hours, we posted up for a quick lunch at the legendary Red’s Eats on Route 1 in downtown Wiscasset. Lobster Rolls are what they’re famous for, and that’s what we got. It’s as good a lunch as I can remember, given the quality of the food, the setting, and how damn hungry we were after cleaning that van all morning.

With all that behind us, and Frank’s blessing for the van, we split for Freeport to party with some local kids before setting off on the big drive. We left grocery shopping for the morning, but loaded the van with our bags of clothes, CD wallets, and video tapes. Crashing hard late that night of June 17, after preparing for this trip for eighteen months, we were ready.

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