49. Jimmy Haile’s Tavern & Weed’s Resort

Two grand houses, south of Douglas on the Lakeshore, are especially seeped in history.

Jimmie Haile’s Tavern in 1999.

Jimmy Haile was one of the Vermont “Green Mountain Boys” of 1812 who came to Michigan to speculate in land and lumber. With his wife, Martha, he operated a boarding house/stage stop/tavern that was the center of 1840s Lakeshore life, known for its hospitality, Saturday night suppers and dances. Conveniently located for a halfway stop when driving cattle or hauling crops between South Haven and Holland, the house had a large third floor room that was the only ballroom and meeting place for miles around. Sometime before 1890 the house was sold to the Phillips family which ran a boys school in it, and then it was owned by the Kraemer family. The house was renamed Lake Shore Manor after restoration by Gordon Aller family in 1960s. Today it is a private residence located at 2749 Lakeshore Drive.

The Weed house in 2008, prior to a major restoration by new owners in the mid-2010s. The private property is located at 2488 Lakeshore Drive.

Joshua Weed began his career as a builder. He built the mill and church at Pier Cove, a mill at Singapore and a mill at neighbor Jimmy Haile’s. He was one of the founders of the Douglas Basket factory. As a farmer he purchased 124 acres of land in 1874 that he planted as orchards. In the 1860s, Weed’s house was moved across the Lakeshore Drive to its present site and enlarged to became the family-run Fernwood Resort — complete with a pier on Lake Michigan to accept travelers and transport fruit to market. Joshua’s sons Perry Weed became an accomplished musician, George Weed became an owner of the Douglas Basket Factory, and Elmer Weed became an owner of Saugatuck’s Big Pavilion.