Meet Caleb

Caleb’s life is the epitome of Catoctin’s urban east meets agricultural west. Much like Abraham Lincoln, he grew up a farm boy who moved to Loudoun and became a lawyer.

Meet Caleb

Caleb’s life is the epitome of Catoctin’s urban east meets agricultural west. Much like Abraham Lincoln, he grew up a farm boy who moved to Loudoun and became a lawyer.

Caleb’s History of Community

Caleb grew up Frederick, Maryland where he was an active 4-H kid and learned patience through the hard work of farm life: milking cows and shearing sheep.

He moved to Loudoun in 1995 where he worked for Home School Legal Defense Association in Purcellville as their Director of Federal Relations. He attended school at night and earning a Business degree in finance with honors from George Mason University in 2001 and a Juris Doctorate from George Mason University, now known as Antonin Scalia Law School in Arlington, Virginia, in 2005. 

Caleb began his legal career with Jim Plowman as an Assistant Commonwealths Attorney for the Loudoun County Commonwealths Attorney Office where he prosecuted criminal cases between 2005 and 2009. Caleb is now an equity partner with the law firm Simms Showers, LLP in Leesburg Virginia.

He attends Cornerstone Chapel in Leesburg, is an avid outdoorsman,  and lives in Hamilton with his wife, Whitney [Emblidge] Kershner, and 4 boys—Colton, Tristan, Brayden, and Weston.

  • Born and raised on a farm in Frederick, Maryland
  • Worked for HSLDA to protect the educational rights of parents and families.
  • Graduated from George Mason University in Finance (’01, B.S.) and in Law (’05, J.D.)
  • Former state prosecutor, and now an equity partner attorney at Simms Showers, LLP in Leesburg, VA
  • Husband, father, Christian, outdoorsman, community leader.

Hear My Story 

Results & Accomplishments

Protecting Property & Religious Freedom

Caleb is a Partner with the Law Firm of Simms Showers, LLP where they represents clients in a variety of areas including church and non-profit, business, employment, personal injury, estate planning, civil and criminal litigation, and family law. One of the firm’s most public cases was on behalf of Cornerstone Chapel in Leesburg, where the firm won a unanimous decision at the Virginia Supreme Court in June 2012. The Court’s landmark case declared that the church had vested rights in their property and not their neighbors, allowing the church to build on its present location in Leesburg, VA.

Fighting for the Interests of Law Enforcement

Caleb has a long history of representing the interest of law enforcement officers in Loudoun and Northern Virginia, including dozens of employment grievances and a Supreme Court victory which awarded deputies working at the Loudoun adult detention center back overtime pay (gap pay) they had been denied for years.

Serving the Agricultural Community

Caleb presently serves as an officer on the Board of Directors for the Loudoun County Fair and Associates—a nonprofit organization which hosts the Loudoun County Fair and is dedicated to promoting youth and agricultural advancement in Loudoun County. He has also been a member of the Lovettsville-Waterford Ruritans.


I’m proud to be endorsed by officials across all levels of Loudoun County government, as well as the hard-working men and women that I strive to represent

Geary Higgins,

Catoctin Supervisor

"Caleb has my strongest endorsement to serve as the next Catoctin District Supervisor. His experience growing up on a farm, background in business finance, and career as an attorney for both the county and private sector give him an impressive range of knowledge that will serve the district well. He has the passion and ability to govern in a way that will preserve the way of life in Western Loudoun we love and enjoy. He will bring balanced and practical solutions to Loudoun’s transportation and land use pressures and will work hard to preserve and grow our rural economy."

Bob Wertz,

Loudoun County Commissioner of Revenue

“Caleb will bring a fresh and balanced approach to the complex land development and financial decisions the Board faces, and I am very pleased to support his candidacy to represent the Catoctin District.”

Michael Dunlap, 

Lovettsville Town Council Member

“Loudoun needs knowledgeable and passionate defenders of our small businesses and small towns like Lovettsville. I am delighted to offer my full support for Caleb and look forward to working with him as our next representative on the Loudoun Board of Supervisors.”

Ready to get involved?

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