Trowbridge Littleton is currently serving as Mayor of Middleburg. He was elected in 2018 and has served three terms. He previously served as a Middleburg Town Council Member and Commissioner of the Middleburg Planning Commission.

Trowbridge Littleton is the President and Co-Founder of HELLEN Systems, LLC, where he has been for seven years. He previously worked as the Vice President of Membership, Business Development, SMC at Aerospace Industries Association for one year. He also worked at Exelis as the Chief Contracts Officer for two years, the Vice President of Contracts & Procurement for one year, and the Director for two years. Trowbridge also worked at General Dynamics as the Contracts Manager for Intelligence Community Business Area for two years.

Trowbridge Littleton attended Radford University where he earned his Bachelor of Science in History and Political Science, the University of Aberdeen for his Law Degree, and the University of Richmond School of Law where he earned a J.D. Additionally, Trowbridge has previously served as the Vice President of the Middleburg Museum Foundation.