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Unexpected Boomer Adventures in Door County, Wisconsin

Are you looking for incredible, but off-the-beaten-path travel ideas for the upcoming year? Well, we’ve got a destination that may be a bit of a surprise for you: Door County, Wisconsin. Maybe there’s not an abundance of travel articles highlighting this beautiful area of Wisconsin, but there should be!

My Itchy Travel Feet featured contributor Debi Lander from ByLanderSea, is here to tell us all about her amazing time exploring what’s become known as “Cape Cod of the Midwest”. Also a popular retirement community, Door County is an extremely picturesque location that features an extensive shoreline, plenty of natural wonders, charming landmarks, and a whopping 2,500 acres of cherry orchards. Yes, the cherry obsession is alive and well in Door County – and for very good reason. 

Exploring Door County, Wisconsin

two red barns sitting lakeside

Door County offers up some idyllic views!

Travel has become a new way of life for many boomers. According to an AARP survey published at the end of 2018, “Boomers take 4-5 trips per year”, some visiting family and others signing up for exciting adventures. Occasionally, vacation spots seem so ideal, folks consider relocating in retirement. And sometimes—they follow through. Door County, Wisconsin, happens to be one of those places.

View of harbour with various boats

Typical view of Door County.

Door County occupies the top two-thirds of the 70-mile long Door Peninsula, the part of the Wisconsin map that looks like a left-handed thumb sticking into Lake Michigan. It’s about 155 north of Milwaukee.

The location gives the county about 300 miles of rugged, rocky shoreline, dotted with 19 towns and villages, 11 lighthouses, and five state parks. Idyllic summer temperatures, 53 public beaches, 34 outlying islands and a bounty of water sports bring people back year after year, generation after generation.

The nickname ‘Cape Cod of the Midwest’ attracts many from the central states. They pack up for an annual Wisconsin road trip and begin to feel stress and tensions fade as they arrive on the area’s two-lane highways. Vacationers flying into Milwaukee or Green Bay (compare flight prices here) should plan to rent a car.

Sturgeon Bay is the largest town, and Egg Harbor is one of the smallest, just a few blocks long with a few hundred residents. But, Egg Harbor has been named one of the best small towns in America and for a good reason.

A sparkling new marina and beach stand out on the waterfront in addition to parks and golf courses highlighting nature’s beauty. Boutiques and specialty shops dot main street offering local artisan crafts, produce, breads, and cheeses.

One of the most enjoyable aspects of Door County is the lack of chain stores; most of the villages have strict ordinances that don’t work for giant retailers. Hence, small locally-owned restaurants, shops, and art galleries flourish.

Where to eat in Door County

two women dressed in red and white gowns

Servers at Al Johnson’s

Noteworthy for breakfast is Al Johnson’s Swedish Restaurant in Sister Bay. (Many Door County residents trace their ancestry to Scandinavia attracted initially by the similar climate.) The Swedish pancakes come topped with lingonberries and dollops of whipped cream.

I highly recommend adding their famous Swedish meatballs. The big draw, besides the fantastic tasting fare, is the architecture. The decorative log structure features a sod roof that acts as home to a herd of goats. Yes, goats on the roof!!

two goats on a green-covered rooftop

Goats on the roof!

For lunch, I suggest a step back in time to a hamburger joint/ ice cream parlor called Wilson’s. Located across the street from the marina in Ephraim, Wilson’s has been a Door County tradition since 1906. Play a tune on the jukebox and enjoy a homemade root beer float with your meal or a sundae for dessert. The cheese curls, a Wisconsin staple, go great with burgers.

street view of wilson's corner store

Don’t miss a stop at Wilson’s.

A traditional dinner in Door County means a Fish Boil, whitefish (the local catch), onions, and red potatoes are boiled in an enormous black kettle over an open fire. The excitement starts when the cooks’ splash kerosene over the flame, creating a fireball that causes the pot to boil over and removes the fishy oils.

This event is staged all-year-round at many of the restaurants. The fish boil at Rowley’s Bay Resort includes a storyteller. FYI, the fish tastes wonderfully moist and tender and the cherry cobbler shouldn’t be missed.

two men in front of a smoking barrel

Fresh fish boil, anyone?

I was surprised to find an authentic Spanish restaurant named parador (small p), featuring scrumptious tapas and fabulous sangria. Chef Michael Reid serves what he calls “food to bring people together”—traditional tapas (small plates) and more modern dishes with a twist.

All their wines are from Spain, all the beer from Wisconsin. Tables in parador span two floors of an 1877 building in Egg Harbor.

plate of food

The tapas at paradore are delicious!

Don’t miss Fred & Fuzzy’s Waterfront Grill in Sister Bay, a perfect spot to catch the sunset. Start with the establishment’s famous Door County Cherry Juice Margaritas. Choose from a casual menu with favorites like the steak and Bleu cheese sandwich or the Three Cheese Deluxe grilled cheese or more hearty entrees.

cherry margarita with lime and salted rim

Have you ever tried a cherry margarita? Divine.

Outdoor Activities in Door County

group of women on a boat.

Girls just want to have fun…

Summer outdoor fun includes relaxing at the many beaches, hiking in the state parks, and exploring lighthouses. Protected harbors create an ideal environment for kayaking or canoeing. Power boaters take to the water for fishing excursions or pleasure rides to enjoy the scenery.

washington island ferry boat

For water-time fun, make sure to take the ferry.

Ferries transport riders to Washington Island year-round or seasonally to Rock Island. A day trip to Washington Island brings many exciting sights.

Drop by the stunning Stavkirke Church, meticulously built by locals, and tour the copy of a Norse medieval church. The expert woodworking honors the shipbuilding techniques used by Vikings.

striking church surrounded by greenery

Stavkirke Church is a local landmark.

Schoolhouse Beach, named for a wooden schoolhouse long gone, is one of the world’s famed limestone or pebble beaches. The shores are covered in smooth rocks, a bit difficult for walking, but great for swimming.

The white limestone pebbles, polished by the action of glaciers thousands of years ago, attracted many souvenir hunters who used to carry them off. Now, anybody found removing stones from the beach faces a hefty fine.

family on secluded beach.

Make sure to take a stroll along Schoolhouse Beach.

The Fragrant Isle Lavender Farm is another popular Washington Island stop, especially when the manicured acres of plants are in bloom. I arrived just as the buds were beginning to show color.

Listen and learn how lavender oil is extracted in a barn demonstration/talk. The property also contains Le Petit Bistro, a small restaurant serving fresh, light fare, plus a lovely gift shop selling aromatic lavender items as well as other giftware.

plate of lavender macaroons.

The lavender macaroons are really delicious!

From Washington Island, visitors may opt to take a second ferry to Rock Island State Park. You’ll dock at the C. H. Thordarson Boathouse, a historic brick structure. It’s filled with fascinating memorabilia from the somewhat eccentric family who owned the island between 1910 and 1945.

pitched roof structure used as a boathouse

Rock Island boathouse is a local landmark.

Today, the allure is hiking the park’s 912-acres of uninhabited natural paradise or primitive overnight camping by permit. Outdoor enthusiasts enjoy circumventing the island on a hiking trail leading to the Pottawatomie Lighthouse, Wisconsin’s oldest completed in 1836.

room full of large furnishings

Interesting stuff at Rock Island Museum.

Another fascinating boat outing crosses Death’s Door, the Portes des Mortes Passage, where Door County derives its name. The course moves above many legendary shipwrecks lying below. Passengers see tiny Pilot Island, a spot that looks like the set of Alfred Hitchcock’s movie, The Birds. Approximately 2,000 pelicans and cormorants nest there, their waste killing all plant life. All that remains is the dilapidated lighthouse, ruins of the Keeper’s House, and the spindly limbs of dead trees. It’s very eerie, especially in the fog, but quite memorable.

view of island surrounded by fog

Kind of spooky, kind of beautiful, Pilot Island really is straight out of a movie.

The Arts in Door County

If the arts are of interest, you’ll find dozens of fine art galleries or you can drop into Hands On Art Studio where you can create your own. Choose from potter’s wheels for throwing clay, metal and glass craft, mosaic and painting projects.

I was amazed at the variety and number of people engaged. All ages, even ornery teens, find something interesting to make. This place is especially popular on rainy days.

woman painting on a canvas.

Get your creative juices flowing at Hands On Art.

The Guenzel Art Gallery at Peninsula School of Art presents exhibitions as well as classes. The 10-acre campus boasts a beautiful sculpture garden.

Two theater options include performances under the stars at the Northern Sky Theater, ideal on a summer night. The Peninsula Players Theater in Fish Creek rests on the lakeshore, making it a romantic spot for sunset viewing. This indoor theater has been entertaining guests for 80 years.

boat in the middle of water at sunset

From land or water, the sunsets here are spectacular!

Local Cherry Obsessions

Think cherries, and think Door County.

Almost all the cherries grown in Wisconsin come from Seaquist Orchards—10 million pounds last year from over 1,000 acres of cherry trees. The bulk of the cherries are the Montmorency variety. No surprise, the family-owned business produces a plethora of cherry products like Bubba Gump did with shrimp.

pot of cherries

Door Co. Cherries

The Cherry Bomb, a jam made with jalapeno peppers, packs a punch when served on crackers. Packages of dried cherries, a tourist favorite, make great gifts or take some home to use in baking projects.

slice of cherry pie

Is there really anything better than homemade cherry pie? I think not.

With all those cherries, you might expect some fruity wines, and you’d be right. The Door Peninsula Winery first began producing varietals nearly 40 years ago. Today, the winery has matured to produce a wide variety of reds, whites, and ports that stack up with the best wines in the region. Other wineries, craft beer and cider galore.

Door County retirement fun

I must admit that the best cherry pie I encountered came from Sweetie Pies. Maybe that’s because I learned how it was made.

At Sweetie Pies, I discovered a group of retirees working in the kitchen. They gather a few times per week, during the busy season, to make hundreds of hand-rolled and hand-filled desserts. The effort reminded me of an old-fashion quilting bee.

group of retirees making pies

Each participant does their part, working together to create deep-dish pies.

Everyone in the group claimed they love to work there because the job brings friendship, a sense of community, and a bit of extra income, especially relevant to retirees. The owner, Olivia Lowery, claims retirees are reliable help.

I found more happy Door County retirees working as boating guides, sales clerks in the art galleries or gift shops. A few couples have even started home-based businesses.

table with freshly made pies

My goodness, that looks like heaven!

What should you consider before retiring in this Wisconsin jewel? Take a look at the differences between summer and winter. Ideal weather and water activities draw summer crowds, falls brings fewer visitors and spectacular foliage, but beware of winter’s cold temperatures.

Door County receives an average of 50 inches of snow and shrinks in population. Retirees should embrace cold weather activities like ice fishing, snowshoeing, cross country skiing, and snow shoveling.

Nature bestows beauty to Door Country all year round, but I suggest a first visit in the summer. You’ll find a welcoming, friendly community, perhaps so captivating you’ll want to return—or maybe even consider a move.

If you fly into Milwaukee to begin your road trip, save time to visit the Harely-Davidson Museum.

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Boomer Adventures in Door County, Wisconsin

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