One of the first businesses open in the now booming Greenbrier area of Chesapeake, Winston’s has been a staple in the community since 1990. Serving fresh and delicious food with emphasis on daily chalkboard lunch and dinner specials. Winston’s has also been an avid supporter of our local music scene by having live music, Karaoke and Open Mic weekly. If you’re looking for a small, locally owned, Mom and Pop place for a casual dining experience with incredible service, Winston’s Cafe is your spot!One of the first businesses open in the now booming Greenbrier area of Chesapeake, Winston’s has been a staple in the community since 1990. Serving fresh and delicious food with emphasis on daily chalkboard lunch and dinner specials. Winston’s has also been an avid supporter of our local music scene by having live music, Karaoke and Open Mic weekly. If you’re looking for a small, locally owned, Mom and Pop place for a casual dining experience with incredible service, Winston’s Cafe is your spot! .