Chatham Squire Restaurant & Tavern — in Chatham, MA

One side of this landmark is an old-fashioned restaurant complete with high-backed booths and red carpeting. The other side features a huge bar and room to mingle. The food is good in either venue. Steak, seafood and chowder are staples in the dining room, while lighter fare is the norm at the bar, where the focus is more on drinking. Cape Cod restaurants come and go, but this popular spot, especially at night, remains a fun place to grab a bite or share a drink with friends.