Admire grey-shingle houses with movie-set-pretty white porches (and rent one if they win you over) or browse crafts, antiques and ‘five-and-dime’ stores on Main Street. If you want to play hard by day and let loose by night, go on a road trip to nearby Falmouth or P’town (Provincetown).

DID YOU KNOW? It’s home to one of the best off-roading experiences a 4×4 owner could dream of. The scenic Outer Beach route winds south for five miles from Nauset Beach in Orleans to Chatham, running down the middle of sand dunes behind the beach. You’ll need a permit, and all the kit.
DIARY DATE In May or late July, visit the Monomoy Islands, a fragile nine-mile-long barrier-beach area south of Chatham, during peak migration. Even if you’re not an avid bird-watcher, the refuge provides nesting and resting grounds for an incredible 285 species. Bird-watching bingo, anyone?
WHAT TO DO Go to a summer concert every Friday night from the beginning of June at Kate Gould Park. If you’re into baseball, catch a Cape Cod Baseball League game at Veteran’s Field.
WHERE TO EAT & DRINK Head to local spot The Squire, self-proclaimed “purveyors of distinguished victuals and spirits, morn ‘til nite”, then to possibly the best-named tavern we’ve ever heard of for seafood. The Impudent Oyster is just off Main Street and we suggest trying the locals’ favourite in this dapper, cosy inn – mussels with white wine sauce.
WHERE TO STAY If you want to be immersed  in history, try the Queen Anne Inn, which was built in 1840 as a wedding present for the daughter of a clipper-ship captain; some of the larger rooms have hand-painted murals, working fireplaces, balconies and hot tubs.
FIND US 515A Main Street, Chatham, Cape Cod, Massachusetts