Chestertown quiets down after dark, except for the restaurants. One local hot spot offers a cozy place to meet friends, play darts, and maybe listen to some music on the weekends: Andy's, 337 1/2 High St. (tel. 410/778-6779; www.andys-ctown.com), features live bands -- everything from rock to jazz to bluegrass -- on Friday and Saturday nights starting around 9pm in a back room filled with couches and a fireplace. The bar has several local microbrews on tap. The atmosphere is low-key, with most age groups represented. Andy's is closed on Sunday; the kitchen stays open until 10pm Monday through Thursday, midnight Friday and Saturday.
The restored Prince Theatre, 210 High St. (tel. 410/810-2060; www.princetheatre.org), presents classic films, community theater, and live musical performances. Lots of children's favorites are offered on Saturday afternoons as well.