The Miss Virginia's Teen competition, part of the Miss Virginia Opportunity, is the pageant that selects the representative for the Commonwealth of Virginia in the Miss America's Teen pageant.
To compete in the Miss Virginia's Teen pageant, a contestant must first win one of many local competitions. Contestants may compete at the local and state level more than once, but having won a state title may only compete in the national Miss America's Teen competition one time. The state pageant is held in Roanoke, Virginia at the Roanoke Civic Center in lateJune.
Caedyn Riddle of Rocky Mount was crowned Miss Virginia's Teen on June 27, 2026, at the Berglund Center in Roanoke, Virginia. She competed for the title of Miss America's Teen 2027 on September 5, 2026, at the Kravis Center for the Performing Arts in West Palm Beach, Florida.
Results summary
The year in parentheses indicates the year of the Miss America's Outstanding Teen competition the award/placement was garnered.
Placements Miss America's Outstanding Teens: Caitlin Brunell (2008) 2nd runners-up: Brittany Young (2007), Emily Kinsey (2019) 3rd runners-up: Casey Shepard (2015) 4th runners-up: Courtney Jamison (2011), Cassandra (Cassie) Donegan (2014) Top 10: Lexie Overholt (2009), Courtney Garrett (2010), Andolyn Medina (2013)
Awards Preliminary awards Preliminary Evening Wear/On Stage Question: Caitlin Brunell (2008), Courtney Jamison (2011), Andolyn Medina (2013) Preliminary Talent: Courtney Jamison (2011), Cassandra (Cassie) Donegan (2014)
Other awards Academic Achievement: Hayley Boland (2016) Outstanding Vocalist: Cassandra (Cassie) Donegan (2014) Outstanding Instrumentalist: Courtney Jamison (2011), Hayley Boland (2016) Teens in Action Award Winners: Andolyn Medina (2013) Teens in Action Award Finalists: Hayley Boland (2016), Morgan Rhudy (2020), Ayana Johnson (2023)
Winners Year Name Hometown Age Local title Talent Placement at MAO Teen Special scholarships at MAO Teen Notes2026Caedyn RiddleRocky Mount16Miss Commonwealth’s TeenMusical Theater Vocal2025Aryana GuestYorktown15Miss Commonwealth's TeenLyrical Dance2024Cassidy LeeWilliamsburg18Miss Hampton-Newport News' TeenBaton Dance2023Addison RhudyMidlothian16Miss Greater Richmond's TeenMusical Theater RoutineYounger sister of Miss Virginia's Outstanding Teen 2019/2020, Morgan Rhudy
Later became Miss Virgina's Teen 2023 & Miss Virginia Teen Volunteer 20262022Ayana JohnsonChesapeake15Miss Roanoke Valley's Outstanding TeenMusical Theater DanceTeens in Action Finalist2021Ella StricklandWarrenton18Miss Commonwealth's Outstanding TeenBroadway Vocal2019-20Morgan RhudyMidlothian17Miss Dominion's Outstanding TeenVocal, "My Strongest Suit"Teen in Action Award FinalistOlder sister of Miss Virginia's Outstanding Teen 2023 Addison Rhudy2018Emily KinseyRichmond 16Miss Apple Blossom Festival's Outstanding TeenPointe Dance, "Friend Like Me" 2nd runner-up2017Isabella JesseeRoanoke 17Miss Southwestern Virginia's Outstanding Teen Violin, "The Devil Went Down to Georgia" Previously Miss Teen Virginia International 20154th runner-up at Miss Teen International 2016 pageant
Miss Roanoke Valley 20222016 Emily Allara Salem 14 Miss Roanoke Valley's Outstanding Teen Dance 2015 Hayley Boland Troutville 17 Miss Roanoke Valley's Outstanding Teen Piano, "Solfeggietto" by Carl Philipp Emanuel Bach Academic Achievement AwardOutstanding Instrumental Talent AwardTeens in Action Award Finalist 2014 Casey Shepard Virginia Beach 15 Miss Apple Blossom's Outstanding Teen Ballet en Pointe 3rd runner-up 2013 Cassandra (Cassie) J. Donegan Smithfield 14 Miss Greater Springfield's Outstanding Teen Musical Theater Vocal, "The Girl in 14-G" 4th runner-up Outstanding Vocalist AwardPreliminary Talent AwardLater Miss New York Volunteer 2024, placed 2nd runner-up at Miss Volunteer America 2025
Assumed Miss New York 2025 title, and named Miss America 2026 2012 Andolyn Medina Chesapeake 16 Miss Arlington's Outstanding Teen Classical Vocal Top 10 Preliminary Evening Wear/OSQ AwardTeens in Action Award1st runner-up at Miss District of Columbia 2019 competitionLater District of Columbia Sweetheart 2019 3rd runner-up at National Sweetheart 2019
Later Miss District of Columbia 20212011 Dominick Fink Chesapeake 15 Miss Greater Richmond's Outstanding Teen DanceLater Miss District of Columbia Teen USA 2014 2010 Courtney Jamison Richmond 16 Miss Chesterfield's Outstanding Teen Piano 4th runner-up Outstanding Instrumentalist AwardPreliminary Evening Wear/OSQ Award Later National American Miss 2013-2014 1st runner-up at Miss Virginia 2015 pageant 2009 Courtney Garrett Pamplin 17 Miss Central Virginia's Outstanding Teen Vocal Top 10 Later Miss Virginia 20141st runner-up at Miss America 2015 pageant2008 Lexie Overholt Oakton Ballet en Pointe Top 10 Currently a member of corps de ballet at Miami City Ballet2007 Hilary MoylerChesapeake VocalN/A Assumed title when Brunell was named Miss America's Outstanding Teen 2008 Caitlin Brunell Great Falls 15 Miss Greater Richmond's Outstanding Teen En Pointe Dance, "Show Off" from The Drowsy Chaperone Winner Preliminary Evening Wear/OSQ Award Daughter of former New Orleans Saints quarterback, Mark Brunell Later Miss Alabama 2014Top 10 at Miss America 2015 pageant2006 Brittany Young Mechanicsville 17 Vocal 2nd runner-up Daughter of Miss Virginia 1982, Beverly Cooke4th runner-up at Miss Virginia 2011 pageant 2005 Elle Elizabeth Bunn Virginia Beach 16 Vocal 2004 Erika Uhlig Earlysville 16No national pageant Later appeared as a contestant on The Bachelor 2003 Brittany Breen Hampton 16
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