Explore the charming shops, galleries, and boutiques along Main Street in downtown Chatham. Visitors can browse for unique gifts, artwork, clothing, jewelry, and more.
Our second home most days and nights - The Squire is a historic tavern and restaurant located right on Main Street. Popping in for a chowder and a beer is a must. Emily highly recommends trying a cup of the 50/50.
This is our favorite restaurant in town and gets crowded quick so go to the bar and get a stool for dinner. They offer a diverse menu featuring a variety of dishes with a focus on seafood and Mediterranean-inspired cuisine. The restaurant has a stylish and modern ambiance, with indoor and outdoor seating options. For reservations call or book on their website well advance.
The Chatham Fish Pier is a historic landmark, working fishing pier, and has a stellar Lobster Roll. The Chatham Fish Pier serves as a hub for the town's commercial fishing industry. The pier is a popular spot for recreational fishing, and visitors can often observe fishermen unloading their catches or casting lines off the pier.
Lighthouse is one of the most popular beaches in Chatham, Massachusetts, known for its picturesque setting and iconic lighthouse. Walking distance from town or you can grab a ride via Chatham Valet from the parking lot at 365 Main St (Chatham, MA).
Part of the larger Cape Cod Rail Trail, a paved bike path that runs 25 miles from South Dennis to Wellfleet that is great for a long Walk / Bike / Run. The Old Colony portion runs 7 miles between Chatham and Harwich. Accessible on Crowell Road in Chatham. Bike Rentals are available at Wheelhouse Bike Co. at 48 Crowell Rd!
Hangar B is one of our all time favorites. It's located at The Chatham Municipal Airport and often voted best breakfast or brunch. No reservations and fills up quickly so expect a little bit of a wait.
About a 10 minute drive from Downtown Chatham, but has ample parking!
Best coffee on Main Street Chatham
Bluefins specializes in Japanese cuisine, particularly sushi and sake. Bluefins has a stylish and modern ambiance, with sleek decor and a lively atmosphere. Recommend sitting at the bar for a quick seating. Can make reservations on OpenTable.
Possibly the best food for lunch or dinner - large portions. Recommend getting take out sandwiches for lunch or sitting at the bar for dinner. "The Oyster" features a variety of dishes made with locally sourced ingredients, including seafood classics like clam chowder, lobster rolls, and scallop dishes, as well as land-based options like steaks and pasta.
Also located in the Chatham Bars Inn, enjoy an offshore breeze and the stunning views of the Chatham Harbor. The menus highlight familiar flavors from all areas of the Mediterranean enhanced with a Cape Cod flair. The Veranda offers the most coveted seats at Chatham Bars Inn on a first come, first served basis.
This casual bar and grill is known for its laid-back atmosphere, friendly service, and tasty pub grub. Good burgers and great beers on tap.
Casual to-go spot on Main Street to grab a coffee, breakfast, or sandwich for lunch
Breakfast sandwiches & coffee