Chatham Travel Guide: How to Spend a Weekend in Cape Cod’s Chicest Town


Cape Cod offers something for nearly every type of summer visitor, whether you’re intrigued by the nightlife of Provincetown, the sleepy charms of Brewster, or the bustle of Hyannis Port. One town, however, stands out above all the rest—especially for the weekend traveler: Chatham, on the southeastern tip of the Cape. This historic fishing community dates back to 1664 and blends quintessential New England charm with a lively downtown and a thriving arts and culinary scene.

Though Chatham is ritzier than some of its neighboring communities, such as Brewster and Harwich, it still retains the rustic, laid-back charm that differentiates the Cape from the haughtier atmosphere of Nantucket. The walkable downtown, with its array of local boutiques, is reminiscent of Martha’s Vineyard’s Edgartown—no ferry ticket required. (Though Cape traffic can be brutal; we recommend hitting the road as early as possible to avoid a standstill on Route 6.) 

A long weekend offers plenty of time for travelers to get a taste of all Chatham has to offer, particularly in the summertime, when the Cape Hydrangea Fest is underway, and you can catch a Chatham Anglers baseball game. Summer visitors can admire the Arts in the Park pop-up downtown, which showcases local artists between June and August, though there are also art galleries open year-round.

From where to get the best lobster nachos to the most idyllic place to watch the sunset, we’re rounding up the best spots to visit for a long weekend in Chatham. Read on and get ready to book your next Cape getaway.





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