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The opening of Bailey Bridge Middle School completed another chapter in the story of Chesterfield County’s race to meet the educational needs of its steadily growing population. Located in one of the fastest growing counties in the state of Virginia, the school provided immediate relief to Swift Creek Middle School whose enrollment had soared to 600 students over capacity. Originally planned for 1989, Bailey Bridge’s opening was delayed two years because of the failure of the 1985 bond issue. This forced the use of trailers and the abandoned Watkins Annex building located six miles away in the town of Midlothian to handle this area’s steadily rising population.

Ground was broken for Bailey Bridge Middle School on April 24, 1990, and with almost perfect weather throughout construction, the building was ready for occupancy on June 7, 1991. Built on thirty acres and costing approximately $12,000,000.00, Bailey Bridge has approximately 127,000 square feet of space designed for an enrollment of 1,200 students. It is the first county school built around the teaming concept advocated for meeting the unique needs of middle school students. The school is organized into grade level areas, which are designed to make the school “user friendly” by eliminating many of the organizational problems experienced by students of this age group. Immediately adjacent to the school property is Manchester High School, which opened in the fall of 1992. Bailey Bridge serves an area bordered by Courthouse Road in the east, Routes 288 and 360 in the north, Amelia County in the west and Bundle Road and Pocahontas Park in the south.

The school opened with 979 students in grades six to eight. Approximately 150 fifth graders were housed at Bailey Bridge to relieve overcrowding at nearby Crenshaw Elementary School during the 1991-92 and 1992-93 school years. The school is staffed by grade level teams of teachers, Exceptional Education teachers, World Languages teachers, career and technical education and visual and performing arts teachers, librarians and school counselors. Mr. J. Michael Rose was Bailey Bridge’s first principal. Mr. Bruce Gillespie became principal on July 1, 1993, when Mr. Rose was named the planning principal of the new James River High School, which opened in September 1994. In the fall of 1998, Ms. Peggy Delbridge became the third principal of Bailey Bridge Middle School. Dr. Deborah E. Marks joined the Bailey Bridge Middle School family as its fourth principal in July of 2002 and served until 2005. Mr. Don Skeen was the fifth principal at Bailey Bridge Middle School, serving from 2005 to 2009. Dr. Mike Gill became the sixth principal on July 1, 2009. Ms. Kume Goranson served as the seventh principal from 2011 to 2017. Ms. Melanie Knowles serves as the eighth and current principal.