This is a short drive from the resort and at the end of Main Street. Worth checking out in the day time and evening! The neighborhood nearby is also a great place for a morning walk as it's lined with historical homes.
Regardless of temperature, Cape Cod beaches are stunning all year round! Chatham Bars Inn has it's own private beach guests can enjoy, or you can explore the popular beach across from the Chatham Lighthouse. Our family's favorite surf side beach is Nauset Beach, about a 20 min drive north of Chatham outside the town of Orleans. The water will probably be too chilly, but be careful as September is peak great white shark season on the Cape!
An iconic restaurant and bar on main street in Chatham. Sit at the bar, order a Harpoon, a bowl of their famous clam chowder or lobster bisque! You can't go wrong with any menu items here as there is something for everyone, even if you are not a seafood lover. This is also a great late night spot!
If you have the time and want to see another side of the Cape, then we highly recommend checking out Provincetown. About an hours drive from Chatham, P-Town is diverse, chock full of art galleries, eclectic shops, and restaurants. The fishing pier is a cool place to walk around as well as the Pilgrim Monument and Museum. Fun fact: P-Town is where the Pilgrims first landed (they actually tried to make landfall in Chatham but the current was too rough) before they decided to move on to Plymouth where conditions were more habitable. P-Town can be visited in a day and we used to love going each year as a family.
Some of our favorite places to eat: -Chatham Bars Inn (can't go wrong at any of the restaurants) -Chatham Squire -Impudent Oyster (our favorite restaurant of ALL time!) -Viera on Main (great raw bar) -Bluefins (if you're in the mood for sushi) -Macs Chatham Fish and Lobster -Chatham Pier Fish Market (a fish market and casual place to grab a bite) -Cuvee at Chatham Inn -Land Ho! (located in Orleans but had to include it as they have incredible clam chowder)