The beginnings of the Oak Street Cottages can be traced back to the last decades of the 19th century with the discovery of gold deposits in the southern end of the Rogue River Valley. The Oregon and California Railroad Company built a line into Ashland, bringing the first train in 1884 loaded with supplies, materials, and new families. The area south of the new railroad track, north of present day downtown Ashland, began blooming with stores, saloons, lodging houses, a library, and even an opera house. Growth slowed during the Panic of 1893, but began again in 1898. The Ashland Railroad District is now on the National Registry of Historic Places.
On Oak Street, just north of Lithia Way, John McCall and his wife Lizzie had built the McCall house in 1883. In the 1890s, their daughter married Eugene A. Sherwin, founder of the Ashland Drug Company and one of the original developers of the First National Bank. The McCalls decided to build their new son-in-law a home across the driveway from their house. The Eugene A. Sherwin house was finished circa 1900 as a one story wooden structure in vernacular style, across the shared driveway from the McCall house in its italianate style. Eugene Sherwin became the regional manager of the Pacific Telephone and Telegraph Company, but passed away in 1914. The Sherwin House stayed in family ownership until the 1930s.
In 1991, George and Patty Walker had an unexpected stay in Ashland when their car broke down on the drive South to their home in Carmel, California. Immediately falling in love with Ashland’s beautiful scenery, amazing culture, and renowned arts scene, the Walkers began looking for property to purchase. They ran across the Sherwin House for sale, noticing its historic value, cozy architecture, and prime location. They purchased the property with two partners, Jim and Jane Hibbert and Jack Swisher. Over the next few years, a massive renovation and reconstruction project ensued with the vision of creating Ashland’s very first vacation house rental property, while retaining the original style and facia of the E.A. Sherwin house. The business plan for the new property developed around the common love of Rotary between the new owners, with the main purpose to support the well-being of others through development of business relationships and friendship.
After many months of work, performed primarily by owners Jim and Jack, led and financed by the Walkers, the renovation of the Sherwin House (Sherwin and Oak Lawn Cottages) and construction of the back building (Oak Hideaway and Oak Tower above, Oak Street Studio below) was complete and the Oak Street Cottages were up and running in 1992. After nearly 30 years of ownership and operation, two of the original purchasers in 1991 have passed away, including Jim Hibbert and George Walker. However, the Oak Street Cottages have become a family run property once again, with George and Patty Walker’s son, Jeff Walker, and grandson, Reid, now managing the property and reservations. With long-time housekeeper Bekki Ellis, bookkeeper Donna Thomas, and several other family members and friends helping where needed, the focus of the Oak Street Cottages has remained the well-being of others and providing the absolute best vacation home rental in Ashland.