American barbecue and Jamaican cuisine are the Cutlass Grille’s specialties. It is a privately owned family restaurant that serves scrumptious, freshly prepared fare. The eatery has truly been a labor of love. When Shawn casually said that he would love to run a restaurant after retiring 25 years ago, Rachel and Shawn embarked on this journey.

Shawn learned to cook alongside his mother as a young child. He had a natural ability to recreate anything his mother made, in addition to a love for learning the food. Shawn realized as an adult that his love and aptitude for cooking were a blessing from God. They recognized Shawn’s Jamaican ancestry and chose the name “Cutlass Grille.” The cutlass, often known as a machete, is a common farming implement throughout the islands.

In 2005, Shawn, Rachel, and their kids began spending weekends working the concession circuit. Jerk Chicken and Jerk Pork, their specialty dishes, were offered. Shawn was anxious to prepare jerk chicken in the Jamaican style. They prayed before deciding to start a restaurant. They started a small eatery in Chesapeake’s Greenbrier neighborhood. The eatery immediately became a locals’ favorite. Every dish Shawn prepares is as though it were for his family. Aside from delectable food, Cutlass Grille serves alcoholic and non-alcoholic drinks. The N/A options are the Heineken non-alcoholic beer along with coffee, Hi-C Fruit Punch, and sweetened and unsweetened tea.