Chestertown

O'Conner's Pub and Restaurant
844 High St

844 high street the only irish pub, owned by an original dubliner couple. family friendly non-smoking facility with pub fare and rotating specials, guinness on tap and a courtyard for outdoor seating during good weather. indoor side bar available for private parties.

Play it Again Sam's
108 S. Cross St.

108 south cross st the towns only coffee shop offering fresh brewed coffee, tea, delicious espresso drinks, sandwiches all day long, homemade pastries, bottled beer and hand selected wine for sale by the case, bottle or glass if seated. you're likely to be in line next to some washington college students, local business owners, professors or the regulars around town. on a hot day or if you are in need of a pick-me up the signature frozen drink, the alaskan, is a tasty espresso/chocolate fusion and the most popular. free wifi to customers and outdoor seating in front of the shop and in a small courtyard in back.

Andys

337 high street lounge-style bar. individuals must be 21 years or older to enter. it is a non-smoking restaurant and bar that offers music as well as weekly specials such as "tapas tuesday" and "meatloaf monday". the food menu and drink menu change seasonally. the variety of entertainment includes a front side room with comfortable couches, a game room, the bar for sitting, eating and drinking as well as tables as you proceed to the back entertainment room. live entertainment is likely friday and saturday. be prepared to pay a small cover fee after 8pm $5 or less.