Westport marked the southernmost reach of William Gilliland's land grants, as reflected in its early name, Bessboro, in honor of Gilliland's daughter. Its permanent name, bestowed in 1815, reflected the role the town played in connecting the Adirondack region to Lake Champlain. Travelers landing at Westport could take a coach up the tollway to Elizabethtown, though many preferred to stay at the Westport Inn, overlooking the lake.
Today, Westport still caters to vacationers with a delightful collection of bed-and-breakfast accommodations. The marina provides services for mariners, including a full-service restaurant.
When the railroad came to town in 1876, Westport developed a second center of activity around the depot, now a thriving summer theatre as well as an active station. The Essex County Fair moved to Westport a decade later. The fairground hosts a variety of special events as well as the county fair in mid-August.