If you’ve ever visited Door County, you’ve probably heard of the famous “winding road.” If you haven’t heard of it, once you cross the bridge into Door County, you’ll see images of it in just about every shop in the peninsula. It’s no wonder… it’s something of a tucked-away gem in an already quite picturesque place. If you hadn’t known about it, you’d be in for a quaint and amusing discovery on your way to the ferry terminal at the northern tip of the peninsula. The road is often referred to as “Jens Jensen’s Winding Road,” dubbed for the famed Danish-born landscape architect whose influence led to this unique spot. Jensen founded The Clearing, a Door County landscape architecture institution, and is a world-renowned figure Door County is quite proud of.

As a photographer, this curvy road is one of my very favorite places to photograph in all of the Midwest. It’s become very popular with tourists and photography enthusiasts alike, especially in the summer and fall seasons. This famed architectural landmark twists its way through lots of trees, making it particularly colorful and scenic in autumn. But my favorite time to visit Door County’s winding road is late winter and early spring. Years ago, I visited on my birthday in March, on a particularly quiet Door County day. It was lightly snowing and — not having seen another living soul — it seemed like I had the peninsula (and that road) all to myself for an entire day. Usually, even on a light day, you’ll encounter the occasional casual photo taker, the back-and-forth traffic to the ferry terminal, or both. I spent well over an hour on that road by myself in total simultaneous serenity and eerie quiet with big, thick, photogenic snowflakes falling all the while I was shooting there. It’s one of the most memorable photo shoots of my life.

Getting There

Just take Highway 42 all the way north following signs directing you to the Washington Island Ferry terminal. As you approach Gills Rock going north, the highway will make a right just before you reach the northwestern tip of the peninsula. Keep going past Bee’s Ho-Made Products and you’ll weave your way through the wooded rural area until suddenly you see it. Deer Trail, a short road going south, is just about the start of the winding road itself.

While You’re There

While it is a popular tourist spot that appears to be in a forest, it is in a rural residential area so I would urge you to mind the neighbors’ properties and keep noise to a minimum. It often gets quite busy, especially during the warm tourism months, and there is no real parking to speak of, so you’ll have to park along the shoulder of the road. I would highly recommend parking further back on the road and cautiously approaching it by foot out of courtesy for other people enjoying the scenery. I’ve been in a group of photographers and casual photo takers whose shots have been ruined by people swooping in and parking their cars farther up the road. I always urge and practice courtesy when I’m out photographing in public so I’d urge others to do the same.

If you’re visiting during busy tourist months in the summer and fall with the intention of taking pictures, I would definitely recommend allowing yourself a little extra time for traffic from the Washington Island Ferry to come and go. I find I prefer no cars or motorcycles in my pictures here, so I often have to wait for intervals of time for vehicles to pass. (Another good reminder — be courteous and cautious of traffic on the road. No pretty Door County picture is worth getting hit by a car while taking pictures, and it’s worth everyone’s time to allow traffic to pass unobstructed.)


While this place is cool for tourists taking pictures with their smartphones — as I often do myself — this place really comes alive with a DSLR camera and the right lens. If you shoot the road with a fairly standard wide lens, you lose a lot of the dramatic curves of the road. If you have a DSLR camera with a long zoom lens and can situate yourself further back zoomed in at a 200-300 mm focal length, the bends of the road really compress together in a very dramatic way.

When is the best time to visit and photograph the winding road? Everyone will have their own answer for this, and it’s really a personal preference. For me, I tend to like shooting here when it’s mostly cloudy or overcast instead of full sun. The road is mostly enveloped in trees, so direct sun will cast a lot of treeline shadows which you may or may not prefer. I happen to like moody, overcast days here, as I think it lends a little more dramatic interest to my shots, more so than bright blue skies. I also like coming here right after a rain storm as the wet road adds a lot of contrast to your photos. Winter is also a very interesting time to come. As I said earlier, a light snowfall casts a really nice effect here.

But whenever you decide to come, be sure to allow yourself some time to just view the place with your camera down and enjoy this quirky gift left to us by Jens Jensen, one of Door County’s most famous sons. It looks great in pictures, but it’s truly a sight to behold in person.