Winter Harbor preserves traces of its past in architecture shaped by seafaring fishermen and traders, nineteenth century summer rusticators, grand public buildings, and adaptation to new opportunities. Channing Chapel, built in 1888 as a Unitarian chapel and now serving as the Public Library, blends Craftsman and Shingle-Style design with stained glass windows; in the winter of 1887, townspeople volunteered to carry field and beach stones across frozen ground so construction could begin more easily in June. The Eureka House, built in 1876 as the town's first summer hotel for the tourist trade, was remodeled and renamed Hotel Hanover in 1888, and after the 1922 Main Street fire it was converted to apartments. Other buildings include a Shingle-Style house at 358 Main Street, a Victorian building from 1888 with Second Empire storefront details and decorative wooden brackets, the First Baptist Church of 1880 with a codfish weather vane and Carpenter Gothic windows at 308 Main Street, the 1877 Old Schoolhouse that now serves as the Winter Harbor Historical Society and combines Queen Anne and Stick styles, Hammond Hall built in 1904 as the Town Hall on land donated by E. J. Hammond and now used for arts performances, the former Baptist Parsonage of 1854 with elaborate Queen Anne carved window details, and the A.B. Whitehouse Store of 1923 with cornice detail and large square dentils along the roofline.