Idlewylde began from a plantation-type summer home, called “Beulah Land”, owned by Joshua Regester. A successful entrepreneur, Regester was born of Welsh origin in 1816 on the Eastern Shore. He married Hester Jones, a native of Wales, and they had 10 children and lived at the corner of Caroline and Chase Streets in Baltimore.
At the age of 28, Regester founded Joshua Regester & Sons Bell Founders and Brass Finishers, which was located on north Holliday Street. The company’s bells were sold and placed across the country, including the Naval Academy in Annapolis (1886), St. Dominic’s Cathedral in Washington D.C., and City Hall in Baltimore (1874). This last bell was affectionately known named, “Big Sam” in honor of Regester’s uncle Samuel. It tolled the time each day and rang for presidential and gubernatorial inaugurations and, for a time, served as the city’s fire alarm.
Regester’s summer home, located on what is now Crestwood Road, sat on 400 acres that extended north to Stevenson’s Woods, south to Walker Avenue, east to Hillen Road, and west to the Birchhear Estate (Anneslie) and the Brown Estate (Stoneleigh). He named the property “Beulah Land,” possibly after the name the slaves of the Underground Railroad gave to their destination, a land of promise where they would be “safe in Beulah Land.”
Regester also owned a strip of land 60 to 80 feet wide extending nearly a mile from York Road to “the farm,” as his property was known. He has it graded with his own farm equipment and later deeded it to the county. The road, Regester Avenue, was completed sometime between 1868 and 1874. Regester died in 1906, a few short weeks of his 90th birthday, and is buried in Greenmount Cemetery in Baltimore City.
In 1914 “Beula Land” was sold to Idlewylde Realty and shortly thereafter Baltimore real estate promoter Harry Gilbert laid out street plans for the neighborhood. The name Idlewylde may have been derived from a passage in one of the Idlewylde Methodist Church’s hymn books, “There’s a little brown church in the wildwood.” The church, built over a period of several years by community volunteers with donated supplies, was dedicated in 1917.
The Idlewylde community now includes several businesses and over 700 homes ranging from the tiny Cape Cods and 1920’s bungalows to brick colonials and Frank Lloyd Wright-inspired designs.