Hop on the harbor water shuttle ($10 for a day pass) to Rocky Neck Art Colony, one of the country's oldest communities for working artists. Once you arrive, you can visit more than twenty galleries and studios to see new work on display; be sure to stop into the cultural center, located in a tiny, steepled church on Wonson Street, where you can see contemporary photography as well as paintings. Afterward, pick up a map of the Rocky Neck Historic Art Trail, and embark on a walking tour of twelve historic sites, including scenes made famous in the work of Edward Hopper and Winslow Homer.
Skip the popular whale-watching excursions and head for the Cape Ann Museum ($10 admission) to see the Folly Cove Designers collection, a series of mid-century linoleum block prints made with exquisite detail by a local community of mostly female textile designers. Also on display are early Winslow Homer sketches drawn during one of two of his extended stays in Gloucester, and the largest collection of seascapes by Fitz Henry Lane, a nineteenth-century Cape Ann artist who focused on the beauty and toil of the working seaport.
Head northwest on Route 127A for a counterclockwise driving tour of Cape Ann that showcases the dramatic ocean views that have inspired poets and artists for more than a hundred years. Stop at Halibut Point State Park ($2 parking fee), the northeastern point of Cape Ann that juts into the icy Atlantic, where you can walk quiet trails, dip your toes into tide pools, and have a picnic on a rocky ledge overlooking the water.