Town of Chatham, Massachusetts

 town (New England / New York), draw only border

Native American tribes who lived in the area before European colonization include the Nauset, specifically the Manomoy or Monomoy people. "Manamoyik" was a Nauset village located near present-day Chatham. Explorer Samuel de Champlain landed here in 1606, contacting (and skirmishing with) the Nauset. English settlers first settled in Chatham in 1665, and the town was incorporated in 1712, naming it after Chatham, Kent, England. Located at the "elbow" of Cape Cod, the community became a shipping, fishing, and whaling center. Chatham's early prosperity would leave it with a considerable number of 18th century buildings, whose charm helped it develop into a popular summer resort.

Chatham is home to the Chatham Lighthouse, which was established by President Thomas Jefferson in 1808 to protect the ships circling the Cape. Originally consisting of two lights, the pair were moved back and rebuilt in 1877. The second was moved to Eastham to become the Nauset Light in 1923, after both were upgraded to rotating lights. Today, the keeper's house is home to a Coast Guard station which tends the light.

Although urban sprawl has started to invade the country and even parts of Cape Cod, the town of Chatham still boasts a quaint and walkable Main Street. Main Street is home to numerous family-owned and -operated shops, restaurants, and businesses. The main shopping area features pedestrian-friendly crosswalks, on-street parallel parking, and some parking lots that are off Main Street. During the summer, concerts are held in a gazebo on Main Street, and not far from the shops is where the Chatham Anglers baseball team plays.