Amid the driving wind and rough waves of Lake Michigan, Captain Justin Bailey peered over the rail of his ship toward the shoreline.

His ship, full of immigrants, freight and grain bound for Milwaukee, sat at anchor in a safe harbor waiting out a storm that had forced them to seek refuge. He had delivered wheat to Buffalo and on the return trip was laden with a cargo that was lighter but certainly more troublesome. The immigrants were on their way West after eventually landing in Milwaukee, and they were impatient to get moving. In the early development of the West, time and seasons were commodities that would not be ignored. Regardless of their impatience, the storm would keep them at harbor just a little longer.

The year was 1848 and Captain Bailey knew a few things about the land that he had traveled past so often on his regular path to Buffalo. He knew that the land that jutted out into Lake Michigan was a part of the state of Wisconsin, but did not yet have an official name. Both Brown and Manitowoc counties hoped to claim the land as a valuable part of their counties. He knew that the only registered town on the peninsula was not even on the peninsula but was the town of Washington, located at the end of the finger of an island.

He may or may not have known of the settlement in the Little Sturgeon area that had existed for two years and then failed. The peninsula was dotted with isolated cabins and a small cluster of rough houses had formed at what would become known as Sturgeon Bay. From this distance, the land beckoned to him.

With his ship safe at anchor in the deep and expansive natural harbor, and unable to proceed until the storm was over, Bailey and a few passengers decided to take the opportunity to go ashore and explore.

The land was thick with mixed timber and had an appealing natural beauty. The rock ledges offered the opportunity for easy quarrying. While they did not encounter any inhabitants, they were pleased to find a sweet alternative to their shipboard diet of salt pork. Wild raspberries grew plentiful just a short way from shore.

They would not venture far into the wilderness for fear of becoming separated and lost. There were no roads, yet occasional trails cut the thick wilderness. The trails were a silent witness that others had once been in the area. Also, they could not be sure of the wolf and bear population, both known to be dangerous predators in Wisconsin. It did not take long for Captain Bailey to assess the value of such land.

When Bailey arrived in Milwaukee, he filed a report with the owner of the ship, Alanson Sweet, a financier who owned a dozen ships, about what he had seen and his perception of the value of the harbor area. The report was so enthusiastic that Sweet followed up with purchasing much of the land in the harbor and by the end of 1849, a cluster of cabins formed an early village. Sweet’s ships were carrying stone and wood out of the area, which required a sizable pier to facilitate the loading of his ships.

By the summer of 1850, Sweet was shipping 2,500 cords of wood annually, approximately 320,000 cubic feet of cordwood. To transport the wood to harbor, Sweet’s men cut a rough wagon road through the thick forest. It followed a path from the harbor to one of the small harbors on the Green Bay shore, opposite Hat Island, in the area today known as Juddville. The road, the first in Door County, roughly follows today’s Highway EE.

Sweet began negotiating with the state Legislature to build a lighthouse on the east side of the bay. In 1851, the first lighthouse to serve a port on the Door Peninsula was constructed at Bailey’s harbor. The lighthouse, at a height of 40 feet, was built on a small island near the harbor entrance. That lighthouse is no longer active today.

Sweet’s work with the Legislature also set the county boundaries, establishing Door County as a separate county. Sweet recognized the value his land holding would have if the settlement were to be the county seat. With no real competition at the time, the rustic and remote harbor community was named the county seat.
Sweet was not enamored with the popular name that had developed for his holdings. Captain Bailey’s report had been heard and reported widely and the enthusiasm of the report naturally led the area to become known as “Bailey’s Harbor.”

Sweet felt that the rocky shoreline and cliffs made one think of Gibraltar, the great rock of the Mediterranean. Rather than have the settlement named after a casual, happy-go-lucky lake captain, Sweet renamed the village Gibraltar, but it was too late. The new name never found favor and the county seat was thereafter known as Bailey’s Harbor, the apostrophe having vanished with time and no longer officially applied to the name.

Sweet experienced great success, but it wasn’t long until he was targeted by a group of rival financiers. They had put their money into rail freight and wanted to eliminate Sweet’s grain boat operation. They found a technical omission in a legal filing and were able to obtain all of his holdings, forcing Sweet into bankruptcy. Sweet was forced to withdraw his connection to Bailey’s Harbor. The piers fell into disrepair, the mill burned down and the cabins went to ruin. For a while, the community literally became a ghost town.

In 1857, with Bailey’s Harbor all but abandoned, eager settlers in Sturgeon Bay saw their opportunity and took the steps necessary to move the county seat to Sturgeon Bay. Posting notices on trees, read only by squirrels and raccoons, which called for an election of a county seat chosen by the people, Sturgeon Bay became and remains the county seat.

While other enterprising men worked in and around Bailey’s Harbor, the real beginning of the village could be said to have begun with Moses Kilgore’s arrival in 1860. An inventive and driven Yankee from Maine, he built the first permanent pier, which allowed Bailey’s Harbor to become a chief shipping point for ties, cordwood and cedar poles. In 1865 a pier was established a mile to the south by William Higgins.

Later, a sawmill and hotel were built in the same area by J.W. Lowell. The area became known as Frogstown, either for the sizable number of frogs in the area or for the French population that began to settle in the vicinity. Kilgore also succeeded, in 1867, in obtaining a state appropriation to build a state road that today runs through the county on the Lake Michigan side; now known as State Highway 57.

After the Civil War, German immigrants settled north and northwest of Bailey’s Harbor, clearing the land, and establishing farms. At the same time, the Irish moved in to the south and settled in the Kangaroo Lake area. Before long, these hardworking, industrious people had established some of the most pleasing farms in the county. In 1870, Bailey’s Harbor became a lively place with schooners regularly coming and going, and farmers coming into town for supplies. Thirsty woodchoppers found six saloons in which to quench their thirst.

Today, Baileys Harbor is located on what is known as the “quiet side” of Door County.

What would the outcome have been had Alanson Sweet retained ownership and continued to be the driving force for the fledgling county seat? How different would Door County look today if Bailey’s Harbor had become the major population center in the county? We can only wonder.