Portland

Maine's largest city has come a long way since its humble origins as a fishing village in 1633. Set on a peninsula that juts out into Casco Bay, it quickly grew to be one of New England's largest ports, a heritage that is still evident to this day. The Old Port is the heart of the city, its lovingly restored brick buildings home to a plethora of shops, cafes and bars. Not too far away, the shipbuilders' Victorian mansions speak of the affluence and wherewithal of its former residents. A small city by most standards, Portland nonetheless wows with its fantastic museums, art galleries and attractions, including the Portland Museum of Art, the Portland Observatory, and the Wadsworth-Longfellow House where the poet, Henry Wadsworth Longfellow, spent his childhood. The Portland Head Light is, however, its most iconic site; dating back to 1791, it is the United States' oldest continuously operating lighthouse. With a craft brew and culinary scene that could rival that of a city twice its size, Portland is a diamond in the rough.