​Planning Your Door County Getaway — May & June 2026 Festivals
Even though February in Wisconsin still feels like winter, there’s good reason for optimism if you’re dreaming about a spring or early summer escape to Door County with us at Olson Cottages. The coming months are packed with excellent local events, perfect companions to a relaxing stay by the lake.

Jacksonport Maifest
Saturday & Sunday — May 23–24, 2026
While we’re not open for Memorial Day, if you’re in the area, Maifest is a long-running festival that we highly recommend attending.  We’ve even marched in the parade in certain years promoting our cottages to thousands.
This long-running spring favorite celebrates the arrival of warmer weather and community spirit in Jacksonport. Expect a lively juried art fair, family midway and entertainment, classic parade down Hwy. 57, food, music, and even a 10K run and fun walk. It’s a great excuse to make Memorial Day Weekend a memory-making getaway.

Door County Wine Fest
Saturday — June 27, 2026
Sip your way through the peninsula’s celebrated wine trail at the Door County Wine Fest in Baileys Harbor. Held at About Thyme Farm, this event brings together local wineries for tastings, live music, food trucks, and scenic farmland views, perfect for an early summer afternoon.

Door County Beer Festival
Saturday — June 20, 2026
If beer and vibrant summer vibes are more your thing, the Door County Beer Festival celebrates craft brews from around the Midwest in a relaxed farm atmosphere just north of Baileys Harbor. Live music and food pair beautifully with local brews.

Peninsula Art & Craft Events
Door County’s galleries and artisan fairs come alive in May and June with special exhibits and craft markets in towns like Fish Creek and Sturgeon Bay,  perfect for finding one-of-a-kind pieces to take home. (Check local listings as dates are announced closer to the season.)

​Why late May/early June are Great for Your Olson Cottages Stay
Planning ahead is the best way to beat summer crowds while still enjoying robust festival energy. Here’s what you’ll love this time of year:

• Perfect weather: mild days and cool evenings
• Fewer visitors: easier dining reservations and quieter beaches
• Local culture: festivals and outdoor activities in full bloom
• Scenic backdrops: blossoms and green landscapes everywhere

Whether you’re sipping wine in Baileys Harbor, exploring art fairs in Fish Creek, or joining the jubilant Jacksonport Maifest parade, May and June are special in Door County, and ideal for your Olson Cottages getaway.
We currently have availability in our lakefront cottages for the week of May 30th and our Greenwood Cottage is available for the weeks of May 29th, June 6th and June 13th (take all 3 weeks and we’ll give you a nice discount off regular rates!).  As always, you’ll find more info, photos and availability on our website at olsoncottages.com.  We look forward to seeing you this Summer!

​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.
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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.

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:

• Families who return decade after decade and make our cottages part of their summer traditions
• Couples who find peace in morning coffee or evening wine by the water
• Adventurers who fill the days with biking, kayaking, or simply exploring what makes Door County magical
• Guests who spend their time relaxing on the beach and braving Lake Michigan temperatures.

Your stories, memories, and photos remind us why we love sharing this little corner of Door County.

The Beauty of Door County Through Every Season
This year gave us:

• Golden sunsets that painted the bay in impossible colors
• Spring blossoms along country roads
• Crisp fall mornings perfect for sweater weather
• Snow-dusted trees that turn the Peninsula into a postcard

Living here, and sharing this place with you never stops feeling like a gift.

The Power of Quiet Moments
We’re thankful for the small things that make a Door County getaway special:

• Deck conversations that last late into the evening
• Bonfires with crackling logs and a sky full of stars
• Kids discovering the magic of nature
• Board games after a long day of exploring
• The simple joy of slowing down

These moments remind us that the best memories are often the simplest ones.

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:

• Preserve the history of this place
• Maintain the character of each cottage
• Keep traditions alive while welcoming new faces
• Pass along stories from one generation to the next

We’re grateful that so many of our guests share their own family traditions with us.
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:

• Better outdoor spaces
• Cozier interiors
• Touches that make your cottage feel like it’s been in your family for generations – and many times it has!

We’re committed to making each visit better than the last.

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:

• Those people and business in our community who lend support to Olson Cottages, especially Annette Schleicher Larson who keeps the cottages looking their absolute best!
• Local farmers, fishermen, and artisans
• Small business owners and neighbors
• The many events and festivals that bring the community together
• The shared pride in preserving the character of the Peninsula

We’re proud to be part of this community and grateful you get to experience it with us.

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

• Best time for colors: Late September through mid-October is typically prime for fall foliage in Door County.
• Off-peak advantage: After Labor Day, crowds thin, parking frees up, and the peninsula feels more relaxed.
• Layering is key: Calm, crisp mornings often give way to mild afternoons — advise guests to pack layers and a light rain jacket just in case.

​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

• Peninsula State Park: Hike the Sentinel Trail or climb Eagle Tower for sweeping views of the foliage.
• Whitefish Dunes / Cave Point County Park: The limestone cliffs at Cave Point are especially striking when framed with fiery leaves.
• The Ridges Sanctuary: Quiet woodland trails with interpretive signs and hidden corners that reward those who wander.

4. Savor Local Flavors & Harvest Traditions

• Fish boils: A Door County tradition still active through October — dramatic, tasty, and unforgettable.
• Apple orchards & cideries: Guests can pick apples, sip warm cider, and shop local preserves.
• Trolley & orchard tours: The Door County trolley stops at spots like Lautenbach’s Orchard to combine color, food, and local charm.

5. Festivals, Events & Seasonal Celebrations

• Sister Bay Fall Fest (Oct 16-18, 2026) — parade, arts & crafts, kids’ carnival, Lion’s Club fish boil, and more.
• Egg Harbor Pumpkin Patch Festival (Oct 10–13, 2026) — live music, pumpkins, carnival rides, and fall treats.
• Baileys Harbor Autumn Fest & Classic Auto Show (Sept 12, 2026 – to be confirmed) — vintage cars, live music, vendors, and fall flair.
• Sturgeon Bay Harvest Fest & Street Art Auction (Sept 19, 2026 – to be confirmed) — food, crafts, street art, and community vibes.
• Door County Fall Lighthouse Festival (Oct 2–6, 2026 – to be confirmed) — special tours (boat and land) to lighthouses that are often closed the rest of the year.

6.  Off-the-beaten-path & Relaxing Moments

• Ferry to Washington Island: Explore quieter scenery, small shops, and fall vistas.
• Lighthouse tours & hidden coves: Enjoy unique vantage points where fall colors meet water, especially in afternoons.
• Sturgeon Bay Bridge Walk: A scenic stroll over both Michigan and Oregon Street Bridges with water views and changing trees.
• Farm markets & shopping local: Fall produce, crafts, and regional goodies are abundant in towns across the peninsula. 

September and October offer the same opportunities as peak season in Door County at a more relaxed pace.  Consider Olson Cottages for your next Fall getaway.  New reservations for 2026 begin in February, 2026.

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.

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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.
​
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!]