Chatham boasts charms aplenty, but we’d be remiss not to lead with its magnificent beaches, which are arguably the best the Cape has to offer. Lay your towel out on Chatham Lighthouse Beach (the namesake tower is open during the summer for visits), where you can gaze out at the fishing boats and seals bobbing in the water. Families will love Harding’s Beach, where the placid, warm waters and diligent lifeguards will help ensure your brood’s safety. And let’s not forget Chatham Bars Inn’s aforementioned stretch of sand, where craft beers and lobster rolls pair perfectly with your private cabana.
Speaking of lobster, no trip to Chatham is complete without indulging at Chatham Pier Fish Market, a cedar-shingled shack where local fishing boats haul in their daily catch. Have the lobster anyway you like it, on a bun, in a bisque or rolled into sushi, or opt for other favorites like scallops, clam fritters or fish and chips. Of course — this being a fish market — you can always just grab and go, but we suggest sitting outside by the weather-beaten pier, where you can be entertained by the local fishing boats and the harbor seals beckoning for your attention.
The town of Chatham bursts with historic homes. Stroll past rambling Victorians and stately Colonials and onto Main Street, where each storefront has a colorful awning. Pop into Monomoy Coffee for a freshly brewed espresso and a bagel, shop for a chic sundress at Violet’s — our favorite All American boutique — or kiss your beach body goodbye at Chatham Candy Manor, home to the freshest salt water taffy. Need a good beach read, or maybe something more of the literary variety? Swing by Yellow Umbrella Books, whose erudite staff will gladly share their latest recommendations.
With its prime location on Cape Cod’s elbow, Chatham’s seafood is — unsurprisingly — spectacular, meaning dining out is de rigueur in this culinary blessed community. Order up the best clam chowder in town at the Impudent Oyster, or nosh on fresh sashimi at Bluefins Sushi & Sake Bar. But the most inspired and progressive cuisine has to be found at Chatham Bars Inn. Not only does the resort boast four restaurants (go gourmet at Stars, or grab an artisanal burger at gastropub The Sacred Cod), it also has an 8-acre farm producing the freshest seasonal greens and vegetables for each menu. New this summer is a pop up restaurant in partnership with Jody Adams, a Boston-based, James Beard Award-winning chef who will be mixing her flair for Mediterranean cuisine with Cape Cod favorites.
You wouldn’t be on vacation without a drink in hand. Transport yourself to 1914 on The Veranda at Chatham Bars Inn, the best place for a sunset cocktail as you marvel at the sweeping views of Pleasant Bay. Feel like something a little less…sophisticated? Hey, we don’t judge. Head to the Chatham Squire, a local favorite right in town. The line to get in can be long and the DJs deafening, but the vibe is always fun and they’ve even got a “dog bar” if you’re traveling with a thirsty four-legged friend.
But for our money, the best nightlife in town happens every Friday night all summer long at Kate Gould Park when The Chatham Band hits the Whit Tileston Bandstand. Gather friends, bring some folding chairs or blankets, and arrive before 8 p.m. for a slice of old fashioned American culture. You’ll hear everything from '30s era classics to “Sweet Caroline” covers, and you might even spot Chatham Charlie, a local Golden Retriever who’s a fixture around town.