InDoor Insider
A BLOG WITH IDEAS, TIPS, FAVORITES, INSIGHTS & RANDOM THOUGHTS
ABOUT DOOR COUNTY
ABOUT DOOR COUNTY
 During this cold snap, its hard to imagine that beach weather is just a few short months away. If you’re craving a glimpse of Door County now, live webcams are a fun way to check in on the beauty and rhythm of this beloved Wisconsin destination—no matter the season. We don’t have a live webcam at Olson Cottages yet, but a well-placed non-streaming camera in Redwood Cottage provided the image that accompanies this piece.
For today, we are happy to share a few webcam options for you to get a glimpse around the peninsula and dream about the warm sand, cool breezes and chilly dips in the lake that will be coming this season. 1. Sturgeon Bay Channel & Maritime Views Get real-time views of the working waterfront and the Sturgeon Bay channel thanks to live feeds hosted by the Door County Maritime Museum and local partners. Watch boats, bridges, and sunsets unfold over the water, great for maritime lovers and weather watchers alike. 2. Cana Island Causeway & Lighthouse Camera This webcam lets you see the shoreline and weather conditions along the causeway leading to the historic Cana Island Lighthouse near Baileys Harbor. It’s especially handy for checking water levels and seasonal conditions before you plan a trip out to this scenic spot. 3. Ephraim & Eagle Harbor Cams Enjoy peaceful views over Eagle Harbor in Ephraim, a quintessential Door County vista with boats, shoreline, and seasonal changes from winter ice to summer sails. 4. The Lodge at Leathem Smith Live Views Catch live marina action and Bayview Bridge scenes right from Sturgeon Bay with the webcams at The Lodge at Leathem Smith, ideal for anyone who loves harbor life and scenic bridge views. 5. Al Johnson's Goat Cam At this time of year, the famous goats are tucked warmly into their winter farm quarters, but the rooftop camera is still working while stacks of Swedish pancakes and plates of Swedish Meatballs are served below. More Views Around the Peninsula In addition to the ones above, there are webcams scattered across the county, from Gills Rock’s shoreline to Fish Creek docks and Northport ferry views—that offer ever-changing glimpses of the Door Peninsula’s lakeside life year-round. Whether it’s winter ice forming along the shore, spring winds whipping across the lake, or summer sunsets and sailboats, these webcams help you feel connected to Door County’s seasons from anywhere. If you’re dreaming about Door County for the upcoming season, our new reservations will be opening up on February 1st. Be sure to check our website at that time for availability. In the meantime, you can check availability for our Greenwood Cottage now and put in your requests. Check things out on the Availability page at www.olsoncottages.com.
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 As the leaves settle, the county quiets, and another Door County season winds down, we find ourselves pausing, grateful, reflective, and filled with appreciation for the people and moments that made this year special. Olson Cottages has always been about more than a place to stay. It’s about connection: to family, to tradition, to Door County, and to the simple joys that make time in Northeastern Wisconsin unforgettable.
Here’s what we’re most thankful for this year. Our Wonderful Guests—New and Returning Whether you’ve stayed with us for decades or found us for the first time this year, you’re the heart of Olson Cottages. We are endlessly grateful for:
The Beauty of Door County Through Every Season This year gave us:
The Power of Quiet Moments We’re thankful for the small things that make a Door County getaway special:
Family Traditions That Grow Stronger Each Year Olson Cottages is built on generations of family, heritage, and Door County roots. This year, we were reminded again how important it is to:
And we’re grateful for our own family, now in its 6th generation, welcoming Sophia Roselyn this past June who joins Josie and Braxton in the latest generation of our family. The Chance to Keep Improving Your Stay From small upgrades to future plans, we’re thankful for the opportunity to continue evolving Olson Cottages. Every suggestion, kind note, or shared experience helps us improve:
And, We’re Thankful for Community Door County is special not only for its natural beauty, but for the people who call it home. We’re grateful for:
Thank You for Being Part of Our Story As we look ahead to a new season, we’re filled with gratitude for the memories made this year, and the ones still to come. From our family to yours, thank you for making Olson Cottages a part of your Door County tradition. We can’t wait to welcome you back next season. With gratitude and our best wishes for a very happy Thanksgiving, The Olson Cottages Family  While we're in our final week of the 2025 season, its never too early to start thinking about next year. If you’re considering Olson Cottages in early fall, you’ll be in the perfect spot. Door County’s shores, wooded hills, and charming towns transform during September and October into a wonderland of color, cozy flavors, and festive energy. Here’s a curated guide to help you enjoy the very best of Door County in fall.
When to Visit for Peak Color & Quiet Charm
Top Things to Do In The Fall in Door County 1. Walk our Beautiful Beach It's always a great time to spend time on our beautiful sand beach on Lake Michigan and Fall is no exception. Sure, the water is a bit cooler and swimming might be a bit more challenging temperature-wise, but the walks are still great and warm days still provide wonderful moments on the beach and on our decks. 2. Drive the Door County Coastal Byway This 66-mile loop (Highways 42 & 57) winds past lakeshore bluffs, orchards, and quaint towns — ideal for leaf peeping and scenic stops. 3. Hikes, Lookouts & Park Trails
Door County isn’t just about shorelines and sunsets—it also holds small windows into its rural past.
Two of the most charming are the Vignes School and the Waniger School, both one-room schoolhouses that tell the story of education in a simpler era.Waniger School, located in Southern Door, right off Highway 57 on the grounds of Southern Door Schools just south of Renards Cheese, was built in the late 1800s and served generations of farm families. Inside, you’ll find wooden desks, blackboards, and even period schoolbooks—an authentic reminder of what daily life was like for local children more than a century ago. Waniger is open some Saturdays during the season so consider a stop on your way to Olson Cottages or on your way home. A bit further north, the Vignes School at the Historic Village at the Crossroads in Big Creek in Sturgeon Bay captures a similar spirit. Restored with care, it transports visitors back to the days when a single teacher guided all grade levels, and the ringing of a hand bell signaled the start of class. Today, both schools stand as community treasures, both relocated (Vignes included a trip over the Bay View Bridge) and lovingly preserved by local historical societies. For visitors, they provide a perfect way to connect with Door County’s heritage—whether you’re reminiscing about your own school days or introducing kids to how different learning once looked. If your stay at Olson Cottages includes a drive through the countryside, be sure to stop by these vintage schools. Or if you're looking for an interesting stop to, from or during your stay, they're right on the way! They’re more than historic buildings—they’re storytellers, carrying the voices of the children, teachers, and families who helped shape Door County. 
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. 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. 1. Peninsula State Park: The Crown Jewel of Door County Parks
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
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
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
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
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!] |
AuthorBen Olson is the fourth generation in the family to manage Olson Cottages and grew up on the Lake Michigan property that is home to the cottages. Now splitting time between DoCo and Milwaukee, Ben enjoys both worlds and shares thoughts from all his decades in Door County, hopefully inspiring or informing our guests and readers about the beauriful Door peninsula and all it has to offer from an insider perspective. Archives
January 2026
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