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Captain Tommy Eskridge: A man on a mission

"Captain Tommy first entered the boat docking scene in 1989."

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Get to know Tommy

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Boat

42-foot vessel powered by a 1150-horsepower C-18 Caterpillar engine

Location

Taylors Island, MD

Years

Extreme Boat Docking since 1989

Captain Tommy Eskridge:
A man on a mission

Captain Tommy helms the Thomas Reed, a 42-foot, 13-foot-wide vessel named after his first-born son, with the names of his three other sons displayed on the boat but not at the bow. Built by Provincial Boat and Marine Limited in Prince Edward Island, Canada, the Thomas Reed is powered by a 1150-horsepower C-18 Caterpillar engine, upgraded three years ago. This powerhouse of a boat can reach speeds of over 30 knots.

Captain Tommy first entered the boat docking scene in 1989, taking first place at the Crab Derby in Crisfield, Maryland. Known for his daring spirit and competitive nature, he traces his passion for boat docking back to childhood, inspired by watching events that captured his imagination. His love for adrenaline now extends to boat racing, where he continues to push boundaries.

 

Beyond boat docking, Captain Tommy is widely recognized for his work with NASA, where he has conducted ocean surveillance and recovered rockets off the coast of Virginia for nearly 25 years. His expertise has also been sought by the Navy, Air Force, Coast Guard, and other agencies, including participation in testing the parachute that landed the Mars Rover. This vital work is a family affair, with all four of his sons—Thomas Reed (28), Jordon Ray (24), Benjamin (20), and Will (18)—as well as his father, William (77), joining him in recovery missions.

Captain Tommy and his wife also run Four Brothers, a restaurant named after their sons. They manage a gift shop on Tangier Island, an Airbnb, and are currently renovating their dock to open a seafood market next summer, offering steamed crabs, shrimp, oysters, and clams. Their ventures reflect a shared commitment to family, community, and the waters they call home.

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