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​At Olson Cottages, we’re not just hosts—we’re locals. And after decades of exploring all the flavors Door County has to offer, we’ve narrowed down some of our favorite go-to restaurants that are always worth the trip (or just down the road).
These are some of the spots we find ourselves returning to again and again, whether it's for a casual lunch or a full family dinner. This is just the tip of the iceberg for great Door County dining and we’ll share more in the future, but to start, here are six of our favorites.
 
1. The Mill Supper Club – Sturgeon Bay
4128 State Highway 42/57, Sturgeon Bay, WI
Open Wed–Sat 4:30–9:00pm, Sun 4:00–8:30pm
 (920) 743-5044
A true local gem, The Mill serves up hearty comfort food with a German twist. Their family-style chicken dinners are legendary, and you can't go wrong with any of the German classics—from schnitzel to sauerbraten. It’s the kind of place where you’ll feel like a regular, even on your first visit.  The bar is vintage, dark and one of a kind, but the dining room lacks the coziness of other supper clubs – the food makes up for it thought.
Insider Tip: Come hungry and come early. Portions are generous but the place fills up on the weekend. 
 
2. Island Fever – Jacksonport
6300 WI-57, Jacksonport, WI
Open Daily 11:00am–9:00pm
(920) 823-2081
Just down the road from Olson Cottages, Island Fever is a family favorite for its handiness, its relaxed vibe and dependable menu featuring a mix of American and Mexican dishes. It’s also a hit with kids—there’s a casual outdoor space with picnic tables, lawn games, and an ice cream and drink shack that’s perfect for a post-beach snack.
Insider Tip: Grab a table outside on a sunny afternoon. The margaritas and street tacos hit just right.
 
3. Kitty O’Reilly’s Irish Pub – Sturgeon Bay
59 E Oak St, Sturgeon Bay, WI
Mon–Thu 11:00am–10:00pm, Fri–Sat 11:00am–11:00pm, Sun 9:00am–9:00pm
(920) 743-7441
kittyoreillys.com
Located out of the way on the west side of Sturgeon Bay, from the outside, Kitty’s looks like your classic neighborhood bar—but step into the backyard and you’ll discover a beautiful multi-level patio surrounded by lush greenery. Their daily specials make every visit a little different, and the menu is full of crowd-pleasers from burgers to fresh fish.
Insider Tip: Head there for a relaxing outdoor dinner and enjoy the atmosphere with a drink in hand.
 
4. Al Johnson’s Swedish Restaurant – Sister Bay
10698 N Bay Shore Dr, Sister Bay, WI
Daily 7:00am–3:00pm
(920) 854-2626
aljohnsons.com
Yes, it’s clearly on the tourist radar. And yes, we still love it. Locals know to come early to beat the crowds and enjoy the peaceful morning buzz. The Swedish pancakes are a must, especially when paired with Swedish meatballs and don’t forget the lingonberries. It’s a true Door County tradition—with goats on the roof, no less.
Insider Tip: Arrive before 8:00am for no wait. If you miss that window and the queue is too long, place a to-go order and enjoy it outside at seating in their outdoor Stabbur bar next door.
 
5. Coyote Roadhouse – Baileys Harbor
3026 County Rd E, Baileys Harbor, WI
Mon–Thu 11:00am–9:00pm, Fri–Sat 11:00am–10:00pm, Sun 10:00am–9:00pm
(920) 839-9192
 coyoteroadhouse.com
Located on the shores of Kangaroo Lake, Coyote Roadhouse offers a mix of cozy indoor dining and scenic outdoor seating with lawn games and lake views. Best of all, it's less than 10 minutes away from the cottages! The menu has something for everyone—try the perch sandwich or the German potato salad. Daily specials keep things interesting, and the laid-back atmosphere makes it a great stop after a hike or day on the water.  It’s close by, reliable and always enjoyable.
Insider Tip: A perfect early dinner spot to catch golden hour over the lake.
 
6. The Boat House – Sister Bay
10716 N Bay Shore Dr, Sister Bay, WI
Daily 11:00am–9:00pm
(920) 854-2622
boathousedoorcounty.com
Since the closure of Fred & Fuzzy’s, this has become one of our favorite spots to watch the sunset in Sister Bay. The second-floor balcony offers a stunning view of the marina—perfect for a relaxing dinner after a day of exploring. The menu leans into fresh seafood with plenty of other options to satisfy all tastes. The lobster roll might surprise you in Door County, but trust us—it’s delicious and worth paying market price.
Insider Tip: Time your reservation for sunset. It's one of the best waterfront views around.
 
More to Come!
These six spots are just the beginning—there’s a lot more to love (and eat) around Door County. In future posts, we’ll dive into some of our other favorites. Until then, enjoy these local-approved favorites and tell them the Olsons sent you (not that it will mean anything to them, but it sounds good!) 😊
 
And don't forget, all of our cottages have fully equipped kitchens if you prefer to do your dining at home.  Check our availability HERE.
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Have a favorite Door County dining spot of your own? Let us know next time you're at the cottage, or shoot us a message—we’re always looking for our next great bite and another favorite to share!

There’s a moment every morning at Olson Cottages when you step onto your deck, coffee in hand, and watch the gentle waves of Lake Michigan. It’s peaceful, perfect, and honestly, you could spend your whole vacation right there.
But for many, the adventurous spirit of Door County will eventually call to you. One of the best ways to answer that call is by exploring the peninsula’s world-class hiking trails. From our central location near Baileys Harbor, you are perfectly positioned to discover the best of both the quiet beauty of the lake side and the iconic bay side bluffs.
Lace up your boots! Here are five of our favorite hikes, all just a short, scenic drive from your cottage.
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1. Peninsula State Park: The Crown Jewel of Door County Parks

• Best for: Everyone! From challenging climbs to gentle, paved paths.
• Distance from Olson Cottages: 15-minute drive to the park entrance.

You can’t stay in Door County without spending a day in the magnificent 3,776-acre Peninsula State Park. It’s close by and it offers trails for every skill level.

• For the Adventurer: Eagle Trail. This is arguably the most famous and rewarding hike in Door County. It’s a rugged, 2-mile loop that takes you down 150-foot limestone bluffs, through a dense cedar forest, and along the rocky shoreline of Eagle Harbor. Wear sturdy shoes, the terrain is uneven and can be slippery, but the views are absolutely worth the effort.
• For a Relaxing Stroll: Sunset Bike Path. This paved, 10-mile path is perfect for a leisurely walk, bike ride, or jog. In fact, one of our family members recently tried out her new e-bile on this path and truly enjoyed it. It winds through the forest and offers stunning water views without the challenging terrain.

Pro Tip: Pack a lunch! There are dozens of beautiful picnic spots throughout the park where you can refuel after your hike.
A park sticker is required for vehicle entry, but the sticker is for your car, not for your person. If the car stays outside, you can go inside without any cost.  See more at: https://dnr.wisconsin.gov/topic/parks/peninsula.
 
2. The Ridges Sanctuary: A Door Couty National Natural Landmark

• Best for: Nature lovers and families.
• Distance from Olson Cottages: 10-minute drive, just north on State Highway 57.

Head north to Baileys Harbor to experience a completely different ecosystem. The Ridges Sanctuary is a National Natural Landmark, protecting a series of 30 ancient beach ridges formed by Lake Michigan over centuries (our cottages are in another bay of ridges, although less visible than The Ridges Sanctuary). The easy, accessible boardwalk and rustic trails wind through a boreal forest, home to thousands of native wildflowers, including 25 species of native orchids.
Why We Love It: It’s a peaceful, almost magical walk. The wooden boardwalks make it easy for all ages, and the historic Baileys Harbor Range Lights are a beautiful photo opportunity. It’s a hike that feels both educational and meditative.
Admission is free, although donations are welcome and memberships are available.  Visit https://ridgessanctuary.org for more information.
 
3. Cave Point County Park: Unforgettable Drama

• Best for: Dramatic scenery and photo opportunities.
• Distance from Olson Cottages: 10-15-minute drive.

Prepare to be amazed. Cave Point is not about long-distance hiking but about witnessing the sheer power of Lake Michigan. The waves have carved stunning sea caves and cliffs into the limestone shoreline. On a calm day, you can hear the water echoing in the caves below. On a windy day, the waves crash against the cliffs in a spectacular display. The trails are short and run along the top of the cliffs, connecting directly to the neighboring Whitefish Dunes State Park for longer hikes.
Pro Tip: Go on a day with a bit of wind to see the waves in action but be sure to stay a safe distance from the slippery cliff edges.  The cliff top areas are full of exposed tree roots and uneven rocks, so they may not be safe for those with balance or mobility issues – stay back a bit if that is you!
Admission to the park is free, although Whitefish Dunes State Park next door would require an admission sticker if you chose to drive in.  More on the park can be found at: .www.co.door.wi.gov/554/Cave-Point-County-Park
 
4. Toft Point State Natural Area: A Walk Back in Time

• Best for: A quiet, reflective hike in an old-growth forest.
• Distance from Olson Cottages: 15-minute drive.

Right next door to The Ridges Sanctuary lies one of Door County’s best-kept secrets. Toft Point is a peninsula covered in one of the last remaining old-growth forests in Wisconsin. A simple, 2.5-mile trail takes you through whispering pines and hemlocks to a rugged, dolomite shoreline. You’ll see evidence of the Toft family’s old fishing camp and kilns along the way.  Long a favorite of the Olson family from the water side, this area is really beautiful from all sides!
Why We Love It: It feels truly untouched. It’s far less crowded than other parks, offering a deep sense of peace and a connection to the peninsula's natural history.
Pro Tip: Bring the bug spray!
Admission is free – this is a State Natural Area, not a State Park: This is the crucial distinction. Wisconsin's State Natural Areas (SNAs) are protected lands focused on conservation and research, with a "leave no trace" ethos. Unlike State Parks (like Peninsula or Whitefish Dunes), they generally do not have facilities and do not require a vehicle admission sticker.
Learn more at: https://dnr.wisconsin.gov/topic/statenaturalareas/ToftPoint
 
5. Newport State Park: Wild and Wonderful

• Best for: Stargazers and those seeking true solitude.
• Distance from Olson Cottages: 25-minute drive.

Located at the very tip of the peninsula, Newport State Park is Wisconsin's only formally designated wilderness park. With over 30 miles of trails winding through dense forests and along 11 miles of Lake Michigan shoreline, it’s a haven for serious hikers. The trails are more rustic and less crowded, offering a true escape.
Pro Tip: As an International Dark Sky Park, Newport is one of the best places in the Midwest for stargazing. Consider heading there after an early dinner for a short twilight hike and an unforgettable celestial show.
A state park sticker is required for vehicle entry. 
More info at: https://dnr.wisconsin.gov/topic/parks/newport
 
The Perfect End to a Perfect Day
After a day spent exploring the trails, there’s no better feeling than returning to your cottage on the lake. Kick off your hiking boots, build a fire in the fireplace or the beach firepit and be prepared for some pretty great stargazing here too.
Ready to plan your Door County hiking adventure? The first step is securing the perfect home base and Olson Cottages is in the center of it all, but happily on the quiet side of Door County.
[Check Our Availability Today!]