Deal Island to Crisfield

Trip dates: 
Monday, September 7, 2026
Trip length: 
1 day
Type of watercraft: 
Sail
  • Boat yard at breakfast; a curious feline gazes in over our transom.
  • Miss, Little Miss, and Master Skipjack 2026
  • The Washington High School Marching Jaguars
  • The Skipjack Heritage Museum float
  • Somerset and Nathan of Dorchester
  • Community beach at Deal Island Harbor
  • View from the bridge between Chance and Deal Island
  • Eldon Willing's (owner of Scott's Cove Marina) deadrise April Star
  • Unstaged Eastern Shore still life
  • "Peaceful Surrender"
  • 67th Annual Skipjack Races
  • Arriving in Crisfield

Dobbs and I celebrated Labor Day weekend in Deal Island.  Festivities commenced with a parade Sunday afternoon, followed by a car show and skipjack viewing with food and craft vendors.  From the beach, we watched Kathryn set sail and two others arrive under sail.

The 67th Annual Skipjack Race was held on Monday.  For us, it was a "lifetime" event, with about 15 skipjacks racing.  Watching the start, mark rounding, and the handling of well-sailed boats was exciting.  Ida May led the fleet, with Messenger close behind, then Somerset and Rebecca T. Ruark.  These last two had a neck-and-neck finish, with Somerset pulling ahead in the final minutes of the race.  Racing wrapped up around noon and we sailed the 16nm to Crisfield.