The Lakeside Inn has a long and varied history, both as a building and as an institution. In the 19th century, the area was a major site for commercial fishing, and for logging. Much of the timber to rebuild Chicago after its disastrous fire in 1871 was shipped across Lake Michigan in boats that were loaded at massive piers near where the Lakeside Inn now stands. The Union Pier was a mile to the south at Berrien Street, in the town named for the pier. Lakeside had its own pier at Pier Street, approximately a half mile to the north of the inn. By the 1890s, however, Lakeside was already becoming a summer resort community for Chicagoans, with its delightful location on the lake, and good railroad transportation. Because the prevailing winds are from the west, it has the best of both worlds as compared to Chicago — cooler air temperatures in the summer, and warmer lake water for swimming.

We are getting ahead of the story, however. Seventy-eight acres including land now occupied by the Lakeside Inn were purchased in 1844 by 58 year old Alfred Ames, who came from Vermont. The area was known as the Clay Banks because sailors used the high clay bluffs as landmarks as they sailed along the lake shore. Ames' wife, Mary, remained in Illinois for the first year while Alfred built  built a log cabin on the property.  This was the first home built on the lake proper in the area.  The first school in the township was at the Ames' house with Mrs. Ames acting as the teacher of the nine children in attendance.  The Ames themselves had two children, Alfred born in 1848, and Fisher in 1856. Alfred Ames died your of small pox in 1864.  At the young age of 12 Fisher became the man of the family and helped his mother open a resort on the lake called Pleasant  Grove. Sunday school gatherings as well as family picnics were the normal event at Pleasant Grove during the summer months.  The Ames' Grove was also the meeting place of the Lakeside Anti-Horse Thief Association, formed in 1876. Legend has it that a horse thief was once hanged from a beech tree on the bluff along the lake, in front of where the hotel now stands.

The most illustrious owner of the property was Arthur Aylesworth. He and his brother discovered the resort as boys on a camping trip, and in 1901 persuaded their parents to purchase it, including almost 30 acres of land for $4,500. Arthur Aylesworth's father died in 1917, and two years later his mother deeded the property to him. He had been a world adventurer, having traveled in South America, and produced films about his game hunting in Alaska. He had toured with Buffalo Bill's Wild West Show, operated a gambling hall and bar in Las Vegas, and had married and divorced Florence Young, the sister of a movie star named Clare Kimball Young. At this time the property was referred to as the Aylesworth Hotel.

After the turn of the century automobile traffic had become more frequent on Lake Shore Road, which went all the way to Chicago, and the inn had to be expanded with the first of what ultimately would be three additions. The building was enlarged to the east, making the axis of the inn running from east to west, perpendicular to the lake. The inn at this point was two stories in height, and a picture of it is displayed currently in the lobby.

A few years later a larger structure was added to the building, on the north, more than doubling its size and increasing the height of the building to three stories. The present lobby and central section of the Lakeside Inn are located in this second addition, which changed the axis of the building to north/south, running parallel to the lake. If you go to the attic of the building, you can still see remnants of the wooden shingled roof above the second floor of the older part of the structure.

In about 1915 the final addition was constructed, three stories tall to the south of the present lobby, comprising the ballroom and restaurant, health spa below, and two floors of sleeping rooms above. This latest section of the building was designed with a large gable at the third floor to match one on the older section of the building. From the front of the inn, one would not notice that it is comprised of several sections, but this is more evident at the rear, where some of the walls are covered with stucco, and others with wooden clapboards.

The hotel is located on a sand dune, and is basically three stories in height, but with an English basement at the rear, which is behind the crest of the hill. It has a half dozen ground floor entrances on its various sides. As far as is known, no architect was involved in its design. It has two large stone fireplaces, back to back, one in the lobby and the other in the ballroom. Across Lake Shore Road to the west is a private beach along Lake Michigan. The inn is approximately 70 feet above the lake, with about 90 stairs down.

Arthur Aylesworth not only operated the hotel, but owned much other property. He was always buying, mortgaging and selling land, in addition to starting the first telephone company in the area, and operating the local water works. As was unfortunately often the case in those days, he was hostile to Jewish people, and the advertisements for his subdivision, called Lakeside Park, contained the assurance these were "Restricted Properties." When Jewish families appeared at the hotel, it instantly became completely booked.

Anti-semitism in Lakeside was not limited to the Lakeside Inn. Dr. Louis Gordon, a physician from Chicago, had been in the habit of renting a house each summer at Rush's Cottages, a Jewish enclave a little north of the hotel. In the early 1920s anti Jewish sentiment became so rabid that fences and even armed guards were employed on each side of Rush's beach, to confine their guests. Signs were put up reading "No Dogs or Jews Allowed." Merchants were pressured not to deliver food or other provisions to Jewish families in Lakeside.

Dr. Louis Gordon's son George, an attorney, took a case all the way to the Michigan Supreme Court. The court did not rule on the civil rights violations to the Jewish families, but did hold that riparian rights to the beach did not permit an owner to construct fences to the water's edge. This is still the law in Michigan today.

Things became so bad that Dr. Gordon and several other Jewish businessmen contracted to purchase an apple orchard in Union Pier, a mile and one-half south of Lakeside, with plans to develop it as the Gordon Beach subdivision. The rest of the investors ultimately dropped out of the venture, for one reason or another, but Dr. Gordon carried out the project himself, including constructing the Gordon Beach Inn in two stages in 1925 and 1929. Union Pier then developed a large Jewish population, and after World War II a significant African-American population.

The most prosperous era for the Lakeside Inn was the 1920s when the economic boom and increased use of the automobile made it a major vacation spot for Chicagoans, and others. Rooms, which rented for $7.50 per night, were often reserved a year in advance, and Sunday dinner cost $2.50. The restaurant employed African-American waiters who worked at the Palmer House in Chicago during the rest of the year. Aylesworth had beautiful gardens, and a mini-zoo behind the hotel, which included a pet bear, deer, goats, and peacocks. There was gambling just off the lobby, and heavy consumption of liquor, especially during Prohibition. In fact, it is said the bootleggers' boats from Canada would beach themselves in front of the hotel, and the guests would wade out into the lake to help unload the cases of whiskey.  

Mayor Anton Cermak of Chicago was a frequent visitor to the inn.  The 1930s brought economic depression, which affected Aylesworth and the hotel. He went bankrupt more than once, but somehow managed to maintain ownership of the inn. At the time of World War II a local farmer sold him 200 chickens every Friday during the summer season, indicating that at least 400 chicken dinners were being consumed each weekend at the hotel. At one time there was a plan to turn it into a retirement home, and the ramp from the lobby to the ballroom was installed to accommodate wheelchairs.

Aylesworth maintained ownership of the property into the 1950s. By that time, his second wife had died. She was an actress, named Virginia Harned, who toured the country in a play called "The Woman He Married," produced by her husband. To this day her presence is felt in the building by many, especially in and near room 30. Years before her death she was shot, but not killed by Aylesworth, who claimed it was an accident. Local belief, however, ran contrary. During the massive rehabilitation of the building in 1995, a towel was found hidden in a wall with Aylesworth's initials on it, and apparent blood stains. The workers on the job speculated that it was related to the shooting decades earlier.

At the end of his life, Aylesworth, who lived in the inn, would watch a tiny television set in the lobby, until he fell asleep. At about 10:00 o'clock each night, the handyman who lived in one of the out-buildings behind the inn, would be awakened, he says by the ghost of Virginia Aylesworth, and he would go to the inn, wake up Mr. Aylesworth, and tell him it was time to undress and go to bed. Through the following decades, many people have detected the presence of the ghost of Mrs. Aylesworth, perhaps most especially artists from Eastern Europe who were there in the 1980s, but also including guests up to the present day. There is less agreement as to whether there's also a male ghost on the premises, presumably Mr. Aylesworth. A guest at a recent wedding in the ballroom swears she saw his outline there, complete with his pet raccoon on his shoulder. In any event, all indications are they are harmless, and pleased with the inn's current reincarnation.

Aylesworth eventually lost the inn to a foreclosure by the Niles Bank. He died in the University Hospital at Ann Arbor, where they did not know of his illustrious background, and almost used his remains for experimentation by the students. A doctor from the hospital, however, happened to mention on the phone to the township lawyer of Lakeside, that one of their residents had died there, and when the people from Lakeside realized what happened, several men went to Ann Arbor to claim the body, and bury it in a plot at the Lakeside Cemetery, which he had purchased many years before. Within a few years the hotel property had been obtained by Bob Creevy, who installed a baby clothing factory in the ballroom, but still rented rooms upstairs during the summer. The property was in a state of some disrepair, and neighborhood youngsters considered at least the upper floors to be haunted. One of their "dares" was for a child to run into an open door of the Inn, run upstairs to the haunted section, and then flee. This reputation was undoubtedly enhanced by the fact that years before, Aylesworth had a stuffed bear in the inn, and a gorilla suit which was sometimes put on to scare people. For example, Tom Dawson, a plumber in Lakeside, remembers when as a young man he was sent on an errand to the dark basement of the inn, someone jumped out at him in the gorilla outfit.

The modern history of the inn is most closely connected with John Wilson, the internationally known print dealer. After obtaining a graduate degree in art from the University of Notre Dame, he was the agent of an old Baltimore art gallery, and traveled all over the country selling prints for them. In 1967 he and his wife Kay purchased the large pink stucco house located on the lake, just northwest of the inn. That house was built in the 1920s by Judge John Sbarbro, who was then the head federal judge in Chicago. Judge Sbarbro had seen a similar house in the south of France, and had it copied on land he purchased from Aylesworth. In 1968 John and Kay Wilson purchased the inn and renamed it the Lakeside Center for the Arts. He ran his print business from several rooms on the main floor of the inn, and converted the large building in the rear into studio space, including print making facilities in association with the well-known Landfall Press of Chicago. For three months each summer, he opened the inn to artists from across the country, and later around the world. Wilson also had activities involving the performing arts, such as one-act plays and concerts in the ballroom, as well as gourmet dinners cooked by chefs brought over from Europe.

During the early years of the Lakeside Center for the Arts, the artists included Richard Hunt, Ed Paschke, and Roger Brown, all of whom are now world famous, and based in Chicago. Wilson is probably best known for the art shows he established at Navy Pier in Chicago during the 1980s. He had seen such shows in Europe, and the WASH ART show in Washington D.C. He later added shows of new art forms, antiques, boats, and flower shows, all under the umbrella of his company, called the Lakeside Group, because most of his investors had summer houses in Lakeside. He demonstrated the tremendous potential for Navy Pier, which resulted in a massive rehabilitation of the facility as a popular carnival type amusement area. At the height of the Cold War, Wilson was contacted by representatives of arts organizations in Eastern Europe, and had many visiting artists from there. He boasts that at one time he had both his personal F.B.I. man, and personal K.G.B. representative.

The current owner of the inn, Devereux Bowly a lawyer and writer from Chicago, first visited it in the 1960s when he was a teenager. He remembers being told that back in the 1920s men could not even sit in the rocking chairs on the front porch unless they had on both a jacket and a tie. He continued to spend summer weekends in the area, and became an ardent architectural preservationist in Chicago. In the late 1980s Bowly rehabilitated a hundred-year-old stable and turned it into a weekend home in Union Pier, and in 1991 he purchased the Gordon Beach Inn at a bank foreclosure auction. That inn, which is slightly smaller than the Lakeside Inn, prospered, and in 1994 Bowly approached Wilson about possibly buying the Lakeside Inn, with the promise to maintain the artistic heritage Wilson had cultivated there for almost three decades. A deal was struck that involved Wilson retaining ownership of the buildings on the rear of the property as a smaller Lakeside Center for the Arts. John Wilson continues to have his office and print sales gallery in the hotel, in a paneled room he removed many years ago from a large mansion that was being demolished, and had reinstalled in the inn. 

During the winter of 1994-1995 Bowly started a massive rehabilitation of the inn, which involved installing private bathrooms for each of its 31 guest rooms, rewiring the building, and renovating the heating system which had not been used in 30 years. For example, eight coats of white paint had to be removed from the pine paneling and trim in the lobby. The present owner has furnished the lobby and the ballroom with wicker furniture, and other antiques which came with the building, as well as with pieces from his own collection of American Arts and Crafts furniture, under the direction of architect John Vinci of Chicago.

To bring life and some degree of economic solvency to the building, Bowly planned a restaurant with wine and beer available to the patrons. A group of neighbors organized against his application for a liquor license, based in part upon their belief that a good restaurant would create too much automobile traffic in the residential area where the inn is located. After more than a year of arguments, cantankerous public hearings, and threats of lawsuits, an agreement was worked out whereby the inn may have a public restaurant of modest size without liquor. Accordingly, the Lakeside Cafe opened in 1997, on the enclosed L-shaped porch surrounding the ballroom, together with a health spa on the ground floor of the building, in the same rooms where one was located in the 1920s.

To this day, the Lakeside Inn is just as popular as it was in the '20s. Now nationally known through WGN Radio and The Washington Post, the Inn is home to many frequent guests and generations of families. The Inn was also designated a State of Michigan Historic Landmark in May of 2004.

For more than a century, through various ownerships, uses, and threats, the Lakeside Inn has prevailed. Bowly says he does not think of himself so much as the owner of the property, but rather as its custodian for present and future generations.

The Lakeside Inn's state historical marker, located next to Lakeshore Road, reads:

"Known as Ames Grove, this property served as a picnic ground and recreation area beginning in the 1880s. John Aylesworth purchased the property in 1901 and opened the Lakeside Inn in this building as early as 1915. The hotel once had its own zoo and extensive gardens. During the 1930s and 1940s Chicago orchestras played at the Inn. The Lakeside Center for the Arts occupied the premises from 1968 to 1994 and hosted artists from around the world. In 1995 the inn was restored to its 1920s appearance."