Michigan has a good handful of “Sleepy Hollow”s throughout the state including a pet cemetery. This particular 'Sleepy Hollow' has a particularly interesting backstory.

Located in South Haven near Lake Michigan, the land that is now Sleepy Hollow Resort was purchased in the early/mid 1800s by R.H. Jones. He turned this twelve acres into a peach farm and named his property “Island Home”.

According to SleepyHollowBeach.com, in 1888, Jones sold his property to Joshua Smith. Smith proceeded to construct a barn, stone bridge, a new house, and a trout pond, stocked with seven thousand fish. Smith had been a friend of the author Washington Irving, and because of their friendship, Smith honored his late friend (who died in 1859) by naming the grounds “Sleepy Hollow” after Irving's story, The Legend of Sleepy Hollow (also known as The Headless Horseman).

It's also been speculated (not proven) that Smith built the stone bridge based on the bridge in Irving's story - Ichabod Crane can cross the bridge, but the Headless Horseman cannot. I wonder if Smith had been friends with some other author like, oh, Mark Twain for example, would he have named the place “Hannibal” or “King Arthur's Court”. Who knows?

97.5 NOW FM logo
Get our free mobile app

Smith wasn't done yet. Soon he added a hotel that accommodated 300-400 guests with just about all amenities: electricity, running water, and toilets.  The property had bloomed to 30 acres and nearby landowners began constructing cottages near Sleepy Hollow.

Smith's health began to deteriorate and he ended up selling out in 1909.

New owners re-named the property 'Brighton Beach Hotel' but in May 1910 before they had the chance to have a Grand Opening, a fire ruined the hotel. With that, the hotel was deserted, leaving Smith's old “Island House” the only thing left. Rumors abounded that even Al Capone invested in Sleepy Hollow, but so far there is no proof.

More owners came and left and by the summer of 1938 it re-opened, advertised as "The Aristocrat of Michigan". Many activities were added including concerts, handball, shuffleboard, swimming pool, and tennis. In the 60s and 70s, additions included an art studio, library, restaurant, and theater.

In the 2000s it is now a condominium with privately owned homes and cottages. It remains a popular getaway for many Michiganders...the gallery below shows the old Sleepy Hollow Resort from the early 1900s!

Sleepy Hollow, South Haven


Inside An Amish Michigan Farmhouse

Magicians in Michigan

Bear Cave: Buchanan, Michigan

More From 97.5 NOW FM