 Dr.
Robert P. Grimesey
Superintendent of Schools
rgrimesey@ocss-va.org
540-661-4550
Extension 1519
Robert P. “Bob” Grimesey, Jr. assumed his
responsibilities as Superintendent of Orange County
Public Schools on July 1, 2009. He brings a
commitment to ensuring that Orange County schools
continue to meet the challenges of the 21st century.
He has been honored twice as a regional
superintendent of the year by the Virginia
Association of School Superintendents. With Orange
County in 2012, he was recognized as superintendent
of the year in Region 4, which includes 19 northern
Virginia school divisions. With Alleghany County in
2007, he was superintendent of the year in Region 6,
which includes 15 school divisions in western
Virginia.
Dr. Grimesey served as a chairman of the VASS
Legislative Committee from 2010 to 2013. In May,
2013, he received the Association’s first-ever
“Director’s Award” for “outstanding service as an
advocate for Virginia public education in the
federal and state policy areas.” In November, 2010,
he was named “Virginia Child Advocate of the Year”
by the Virginia Parent-Teacher Association.
In October, 2012, Dr. Grimesey was selected from a
pool of national nominees to receive the 2012
“Outstanding Superintendent Award,” sponsored by the
Curry School of Education Foundation. The award is
presented annually to a graduate of the University
of Virginia’s Curry School of Education.
Prior to coming to Orange County, Dr. Grimesey
served as Superintendent of Alleghany County Public
Schools from July, 2001 through June, 2009. In
November, 2004, Dr. Grimesey was named “State
Administrator of the Year” by the Virginia Music
Educators Association. In February, 2005, he
received the “Curriculum and Instructional
Leadership Award” from the Virginia Technology
Education Association.
Prior to his tenure in Alleghany County, Dr.
Grimesey served from 1987 to 2001 in Rockingham
County Public Schools as assistant principal of John
C. Myers Middle School (1987-1991), principal of
Ottobine Elementary School (1991-1994), principal of
Spotswood High School (1994-1998), and director of
grants and partnerships (1998-2001). He began his
administrative career as assistant principal at King
George Middle School (1986-87). Prior to becoming an
administrator, Dr. Grimesey taught social studies
and coached football and wrestling at Harrisonburg
High School (1982-1984), and at Osbourn High School
in Manassas City (1985-86). He also served as a
graduate assistant at James Madison University
during 1984-85 while he completed work on his master
of education degree in school administration.
He graduated from Fairfax County’s Annandale High
School in 1974, where he played football under
legendary coach Bob Hardage. Dr. Grimesey received
his Bachelor of Science degree in communication arts
from James Madison University in 1978. He served
stints as a staff writer and sports writer for the
Harrisonburg Daily News-Record between 1977 and
1984. In 1978, Dr. Grimesey earned first-place
awards from the Virginia Press Association for “Best
Sports Feature Article” and “Best Series of
Stories.” He worked as an agricultural volunteer in
Israel during 1979-1980. Dr. Grimesey completed his
master’s degree in 1985 and he received his Doctor
of Education degree in leadership and policy studies
from the University of Virginia’s Curry School of
Education in May, 1991.
He married his wife, the former Carol Y. Martin, in
1982 and they reside in the Locust Grove area of
Orange County. Their oldest child, John, serves in
the United States Air Force. They also have two
daughters: Sarah, who teaches English at the
American College of Sophia, Bulgaria; and Hannah,
who resides at home.
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