A Traveler's Guide to Baileys Harbor, WI

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Welcome to beautiful Baileys Harbor! If you’re looking for a unique and unforgettable getaway in the Midwest, this small town on the shores of Lake Michigan is the place for you.

A vacation home rental in Baileys Harbor is excellent for anyone looking to enjoy the outdoors or just take advantage of the slower pace of life. This charming lakeside town has plenty to see and do within walking distance. It’s the perfect place for families or friends looking for quiet time or nature buffs who want a more adventurous escape.

Let’s look at what makes this scenic Wisconsin town one of the best-kept secrets of Door County.

About Baileys Harbor

Baileys Harbor is located in Wisconsin on the Lake Michigan side of the Door Peninsula. The town is built along the eastern shore, so it's not hard to find a good view from anywhere in the area, especially if you love to catch a good sunrise.

At just under 30 square miles, Baileys Harbor packs a lot into a small space. This coastal Lake Michigan town is bustling with small-town charm.


Photo Credit: Nejdet Duzen

The town of Baileys Harbor is any outdoor enthusiast's dream. In fact, Door County is well known for holding some of the best hiking in the state. The peninsula’s lush forests, quiet lakes, and rocky shorelines are just a short drive away from central Baileys Harbor.

Baileys Harbor is also home to two nature preserves, two county parks and several state parks within close proximity. With miles of shoreline and gorgeous lake views, visitors can find plenty of swimming, fishing, camping, and hiking opportunities.

Scenic Views

The geography of the area makes it ideal for exploring. Located on Lake Michigan's western shore, Bailey's Harbor is known for its breathtaking views. Visitors can take in the lake's majestic views from the harbor or take a scenic drive along the shoreline's rustic roads out to the Toft Point Nature preserve.

The harbor itself is quite unique. It’s the only natural deep-water harbor in the region. Boating and fishing are popular activities, as most of the area’s waters are relatively calm. With two accessible beaches, Anclam Beach and The Ridges Park Beach, It’s also an excellent spot for sunbathing and beach-combing.


In Baileys Harbor, you’ll find a quaint downtown area with plenty of local businesses providing a homey feel. From tasty restaurants and unique shops to craft breweries and farmer’s markets, there’s something for everyone in Baileys Harbor. 

The best part about the center of the town is that everything is within strolling distance, making for a carefree exploration of all the downtown has to offer. 


In addition to its natural appeal, Bailey’s Harbor is home to a wide array of restaurants, grilles, shops, and waterfront resorts. There’s also an array of nightlife activities, ranging from live music venues to cozy craft breweries.

The Harbor Fish Market and Grille serves up a famous local whitefish chowder, while the  Florian II Supper Club boasts BBQ ribs with the best views of the lake. If you’re in the mood for a little nightlife, you can enjoy live music at the famous, locally-owned Door County Brewing Co.

The History of Baileys Harbor

Photo Credit: Kenneth Keifer

Baileys Harbor has a rich history. Having been settled by the Menominee tribe centuries ago, it was officially founded as a lumber port in 1848 by Daniel Whitney Bailey along with his brother Elijah. 

During this same period, Josiah Ogden Watson built a grist mill nearby that became one of the community’s most important early industries. This historic site has since become known as Pioneer Park and is listed on the National Historic Register. 

According to the Baileys Harbor Historical Society, our very own Harbor House was originally owned by Louis Prueter, who owned a sawmill that was considered to be a town landmark until it burned down in a devastating fire in 1923. The Harbor House served as Mr. Prueter's private residence and later was passed down to his children.

Over its 155-year-long existence, it has transitioned from a lumber port to a popular tourist spot. While the town is now known chiefly for its picturesque harbor, the area's history still runs deep.

Historical Sites

Photo Credit: John Touscany

One of the best ways to get acquainted with Baileys Harbor's history is to take a stroll around the town. 

Here, you'll find old buildings, some dating back to the early 19th century, churches, unique shops, and plenty of historical markers. In addition, you can visit the nearby Cana Island Lighthouse, which has stood strong since 1883, and take in the amazing views of the harbor and Lake Michigan beyond.

As you explore the town and its surroundings, it's easy to imagine how it looked two centuries ago. Learning about the town's history will make your visit even more enjoyable no matter what brings you to Baileys Harbor. 

What To Do

Baileys Harbor is an ideal destination for all sorts of travelers. Whether you're an outdoor enthusiast looking for adventure, an art lover searching for inspiration, or a family seeking a quiet retreat, you’ll find plenty to do in this quaint lakeshore town.

Explore The Surrounding Nature

Photo Credit: Matt Sampson Photography

For those interested in exploring nature; there are plenty of opportunities here. From exploring the Ridges Sanctuary Nature Center, Wisconsin's first land trust, to hiking through the Boreal Forest and Wetlands State Natural Area and the shoreline trails at Bjorklunden, there is plenty to do along the miles of hiking trails, campgrounds, and state parks in the area.

Suppose you're looking to go a little further. In that case, nearby Toft Point State Natural Area, Newport State Park, Kangaroo Lake, and Peninsula State Park all make for incredible sightseeing experiences around the peninsula. 

They are all great places to take a leisurely stroll along the lakefront or to embark on a full-day adventure of kayaking, fishing, and bird-watching.

Discover The Town

Downtown Baileys Harbor is supported by a vibrant local community and artisan culture. This small charming town holds secrets around every corner. Let’s take a look at what makes this town such a great getaway destination. 

Museums and Galleries

You'll find everything from unique folk art to vibrant paintings and sculptures in town. Many galleries feature work from local and regional artists, and many offer workshops, lectures, and other educational activities. 

Check out the iconic Door County Maritime Museum or discover the local artist community at the Baileys Harbor Art Center for an inside look at Bailey Harbor’s vibrant art community.

Take a Tour of the Town

Get acquainted with the charming downtown by taking a walking tour. You’ll see the historic lighthouses that dot the shoreline, explore the streets lined with galleries and boutiques, and hear fascinating stories about the town’s past. 

The online platform Clio offers a self-guided walking tour through the historical sites of interest in Baileys Harbor that you can follow along with audio narration. 

Visit the Marina

Photo Credit: John Touscany

Whether you’re looking to take out a fishing charter or just explore the area’s nautical history, the Baileys Harbor Marina is a must-see. You can also find some of the best seafood restaurants in town here

Shop Local

The Baileys Harbor community has many local artisans and craftsmen. This small town is home to a variety of unique shops and boutiques. Whether you’re looking for handmade gifts, antiques, or vintage clothing, you’re sure to find something that will remind you of this charming town.


Looking to perfect your swing? Baileys Harbor has some of the best golf courses in the region. Whether you want to play a few rounds at the local public course or look for a more challenging round at one of the private clubs in the area, you’ll find plenty of opportunities to practice your golf game.

Breweries and Wineries

Baileys Harbor is home to several local breweries and wineries, offering visitors a chance to sample some of the region’s best craft beer and wine. Stop by one of the local watering holes and grab a beer flight or a glass of wine, and you’re sure to enjoy a locally-sourced and enjoyable experience.

The Different Seasons of Baileys Harbor

Spring and Summer

Spring and Summer are ideal times to visit Baileys Harbor and explore the local area. With mild temperatures and plenty of sunshine, it’s the perfect place to relax and enjoy the outdoors. Just keep in mind, spring starts a little later in these parts. Spring typically doesn't show it's pretty face until the end of April and even into May.

Not only does Baileys Harbor boast the Midwest's most spectacular array of spring wildflowers, but it's also home to a wide variety of festivals and events throughout the summer months, including the Renaissance Festival and the Baileys Harbor Lighthouse Festival.


If you prefer cooler weather, Baileys Harbor offers plenty of activities to do during the fall season, such as kayaking, biking, boating, and hiking. The nearby scenic trails are the perfect place to explore and take in the breathtaking views of Lake Michigan and the surrounding foliage.


Winter is also a great time to visit Baileys Harbor as it’s generally less crowded than other times of the year. Snowmobiling, snowshoeing, ice skating, and cross-country skiing are popular activities along the area's many groomed trails.

For a unique experience, visitors can also take a winter tour of Cave Point. This cave offers a chance to explore an underground river and its many limestone formations. 

No matter the season, there’s always something to do and see in Baileys Harbor.

What to Pack When Visiting Baileys Harbor

Baileys Harbor is known for its cooler temperatures, so you should be prepared for various weather conditions. Be sure to bring:

  • A long-sleeved shirt and a light jacket.
  • Jeans and other sturdy fabrics.
  • Comfortable walking shoes and hiking boots.
  • A hat, sunscreen, and sunglasses for sunny days.
  • Rain jacket and umbrella for rainy days.
  • A swimsuit or other water recreational equipment.
  • A fishing rod, tackle box, and other supplies for a day out on the lake.

Escape To Baileys Harbor

Baileys Harbor is waiting for you to explore. It is the best of Door County’s history, culture, and scenery, as well as one of Wisconsin’s best-kept secrets. 

So pack your bags and prepare to experience a truly special getaway at one of Moonsail Vacations’ charming vacation homes.