On the southwest edge of Penobscot Bay, Rockland has long been proud of its brick-and-blue-collar waterfront reputation. Built around the fishing industry, Rockland historically dabbled in tourism on the side, but with the decline of fisheries and the rise of Maine's tourist economy, the balance has shifted. Rockland is swiftly being colonized by creative restaurateurs, innkeepers, artisans, and other folks who are transforming from fish-processing center to arts-and-crafts center.

The city's waterfront has a small park from which windjammers come and go, but even more appealing is Rockland's downtown -- basically, one long street lined with historic brick architecture. If you're seeking picturesque harbor towns, head instead for Camden, Rockport, Port Clyde, or Stonington. Rockland is best as a local base for exploring a beautiful coastal region, especially if you like your towns to be a bit rough and salty around the edges.