Best of Boston

Overflowing pints of Bass and Guinness, live entertainment including Karaoke Tuesdays, the obligatory logo-embroidered polos for sal—smack in the center of Chatham, the often rowdy Squire is the quintessential Cape pub. Weekend nights host a medley of thirsty characters; stick around long enough, and you’ve got good odds of witnessing unlikely, though not altogether uncommon, end-of-the-evening trysts between local anglers and summering society types.