Please note that location entries may feature older photos or post card views that may not represent the current appearance, features, addresses, phone numbers, or contact names of the attraction. This site is intended to be a historical as well as current record of various attractions but it is not always possible to have up-to-date information due to the vast number of locations featured here. We ask you consult the propietor for current information.
From the Website
A BRIEF HISTORY OF SLEEPY HOLLOW RESORT
The land that now houses the Sleepy Hollow Resort was farmed and purchased by R. H. Jones. Mr. Jones' peach farm encompassed 12 acres and he named it "Island Home", perhaps because a lovely ravine surrounded it.
In 1888 Joshua Smith, a professional photographer from Chicago, bought the property for $2,800 and set about creating a new house, barn and a 7,000 fish trout pond. Smith had stone brought over from Chicago and built a lovely bridge at the entrance to the estate. Smith and his wife Louisa hosted many sumptuous parties some featuring an orchestra or a special evening of poetry readings. The "Island Home" estate was extremely serene and Smith, who originally hailed from upstate New York and was a friend of the author Washington Irving, decided to name the grounds "Sleepy Hollow". He now set about building a large 300- guest hotel.
The hotel cost $30,000 and incorporated the most modern accoutrements: running water, toilets, electric lighting and interior walls from a new material called compoboard. The estate was now 30 acres and along the outer boundaries of the property people began to build small cottages. Guests from Chicago came by train and boat and were transported from town by a horse drawn colorful omnibus covered with a colorful canopy top. The ads indicated that in this "miniature canyon" one could enjoy the beach, fishing, golf and concerts performed on a special automatic organ brought from the "windy city".
The Smiths tried to make a go of the hotel and even had as many as 400 guests a week but for some reason the enterprise began to falter and a now ailing Smith sold the Hotel in 1909. The new lessees were a couple who split the duties of the hotel. Frank Winter took care of the daily operations and his partner Eleanor Paradis organized the social activities. They renamed Sleepy Hollow, 'Brighton Beach Hotel' and advertised enthusiastically. Their plans were short lived when a suspicious fire raged through the building just prior to the summer opening in May 1910. Sleepy Hollow now became desolate and deserted.
Smith's 'Island Home' was all that was left and Smith's widow Louisa lived there until she died in 1927. A number of owners and tenants are listed in the archives following the Smiths. Now in the era of the bombastic 1920's, new cottages and "swell" homes began to appear along the South Haven shore. AI Capone was purported to have invested in Sleepy Hollow but perhaps these are myths rather than hard facts. With the depression of 1929 vandals denuded the once proud home and the desolation of Sleepy Hollow became an even greater reality.
The next owner was Chicago resident F. S. Demeter but his stay was short lived and in 1937 he sold to Mr. Edward Gray, president of a construction and demolition company. Mr. Gray was a foresighted man who was influenced by the art deco architecture used in The Century of Progress 1933 Chicago fair. The geometric simple lines of the art deco 1926 style were prevalent in many of the buildings at the fair and Mr. Gray engaged architect Elmer C. Carlson to design the Resort with this style in mind.
Mr. Gray's construction started at the northern perimeter in the original Jones orchard and cornfield. His cottages offered stainless steel sinks, modern electric kitchens, full baths with showers and inner spring mattresses of a new design. In the summer of 1938 he was now ready to open a first class resort and to advertise it as "The Aristocrat of Michigan". In addition to shuffleboard, tennis, handball courts and beautiful flowerbeds he had indeed made Sleepy Hollow a 30-acre estate of quiet splendor.
Edward Gray was an amateur violinist and because of his love for classical music, he constructed a music tower that emitted daily-recorded afternoon concerts. In the early 1950's he added an Olympic style heated swimming pool, which was received with great enthusiasm.
Edward Gray died in 1962 and the property passed on to his son Richard, an art dealer who proceeded to add his own special touches. In the 1960's and '70's Sleepy Hollow Resort was now one of the premier family vacationing spots. A public restaurant opened on the grounds. Richard Gray initiated an art's festival, stocked a library, created an art studio, a theatre and made all types of music and theatre an active part of a guest's visit.
In the late 70's the Gray family gradually relinquished their complete ownership and the resort became a condominium association with all the units now privately owned. Ichabod's Restaurant and The Legend Theatre leased their operations and reported to the Association Management until the barn theatre was razed in 2002 and the restaurant ceased operating.
In 1997 the Sleepy Hollow Condominium Association met to propose an extensive four-year reconstruction project for the resort. Four years later it was completed with a new infrastructure, new homes and new landscaping.
The various Boards and the Condominium Association have worked very hard to do service to this historic and beautiful landmark property.
Written and compiled by Jeanette Stieve, and Lynn M. Lyon 2005