Woodlawn is home to the Social Security Administration and the Center for Medicare and Medicaid Services, providing stable employment to many residents in the area. Although Woodlawn is so deeply associated with the government organizations that it has the nickname, Security, it also has a beautiful historic neighbor that is one of the area's best kept secrets. The small neighboring town known as Dickeyville is a former mill village located along the Gwynn's Falls. Purchased and rehabilitated in 1934, developers took special care in preserving the town's distinctive character and the 1940's era homes were designed to be indistinguishable from the original, late-Victorian style workmen's homes.
Shoppers flock to Security Square Mall, which remains one of the largest shopping centers in the Baltimore area. Retail shops including Sears, Old Navy, and the eclectic Seoul Plaza, movie theatres, and restaurants, make Security Square a popular attraction for families living Gwynn Oak, Woodlawn, and other neighborhoods close by.
Catonsville, Woodlawn's popular neighboring town also features a number of fun recreational activities. Catonsville is home to many historical sites and museums, such as the Benjamin Banneker Historical Park and Museum, The Townsend House and Pullen Museum. However, the suburban town offers up much more than a taste of Maryland history. Catonsville hosts a popular Fourth of July Parade and several Arts and Crafts Festivals. In addition, there are many shopping centers, restaurants, and movie theatres along Catonsville's heavily trafficked Route 40.