Patrick Dempsey is a lot of different things to a lot of different people: teen icon, onscreen brain surgeon, McDreamy, spokesperson, Le Mans competitor, race team owner and philanthropist. But throughout it all, he has always been a Mainer.
So with InsideHook sharing our favorite road trips for summer later this month, it seemed only fitting to ask Dempsey for tips on driving through his home state during our chat about his eyewear ambassadorship with Porsche Design. This story appears as told to Charles Thorp, and has been edited and condensed for clarity.
I try to get back to my home in Kennebunkport at least once a month, as long as work doesn’t keep me on the West Coast.
I suggest that if you are visiting Maine from somewhere else, the best move is to fly into Boston and drive all the way up to Acadia National Park. It is an absolutely magnificent drive. You never know what kind of weather you are going to get, but no matter what, it’s beautiful. Every time that you stop there is a conversation. Everywhere you go feels like a small town.
Do it with a convertible if you can, so that you can see everything the state has to offer. I would do a Porsche 356 Cabriolet, because with a car like that you aren’t just driving, you are making a style statement. It’s not so flashy that people will raise an eyebrow; the people of Maine aren’t about the flash, they are very down-to-earth. They hold on to things and fix them. This car has a warmth to it. It is an icebreaker, and it pulls people to want to have a chat with you.
Of course if you are driving a convertible, you want to make sure you have the right layering of clothes, a good jacket and perhaps a scarf. Be sure to have a comfortable driving moccasin, too: they are making some great ones in Maine. I keep my Porsche Design sunglasses in the glove compartment, along with my reading glasses. I make sure to have a pair in the car at all times, that way you are never missing them on the road. I use the 8688 model because they are light titanium and don’t scratch. They build them right, like their cars.
For music, I use the KCRW app. That’s the absolute best, because they play some great music: not just old songs that you love, but great new music that helps you build new memories. I love all of the old jazz, like Miles Davis or albums like Gentle Side of John Coltrane. Those tunes allow you to just kick back and cruise.
The first thing you do when you get into Maine after making your way through New Hampshire is grab a lobster roll. There are so many great restaurants along the way these days, with these incredible young chefs who are experimenting with cuisine in the region. You really can’t go wrong with the roadside spots. If you see something that looks good, turn off and give it a try.
One of the first towns you will hit is Kennebunkport, where I live. There are a lot of amazing places to stop for a bite, and people have really tried to support them during this past year. I have to recommend a stop into Musette.
The next stop is Rockland, where you go check out the museum and the Wyeth Center. There are so many things to explore. Getting back on the road you can stick with your coffee, or if you are feeling particularly adventurous with your drink options, you should check out the Maine soda Moxie. There’s a place called Graffam Bros Lobster in Rockport where you can still get it in the bottle.
One of the other crucial food destinations is Lost Kitchen, which has incredible food and is in Freedom, Maine. The rest of the trip up takes you by Moose Point State Park, and if you are in a convertible the wind will be brushing on your face.
Once you are in Acadia try to get a mountain bike and explore all the little carriage roads in the park. There is so much great mountain biking in the area. Give yourself as many days as possible, so that you can hit each of the little towns in the area, too.
During the nights when you are done driving around, have a copy of The Maine Woods by Henry David Thoreau. It gives you a real taste of what the wilderness in Maine is like. It is still one of my dreams to do that exact route that he did in a canoe, which I hope to get to soon.
There is always more to discover in Maine, and I find that even for myself, that is still the case.
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