Worcester Square in Boston's South End (©Henry Zbyszynski/Flickr, Creative Commons)
This enclave jumps right from the pages of a Henry James novel and is actually on the National Register of Historic Places as the country’s largest Victorian row house district. Tree-lined streets often boast their own wrought-iron-fence-bounded parks, and historians love wandering around to discover them. Food fans go wild for the sheer volume of amazing restaurants, while culture vultures devour the vibrant art scene. The South End is also widely known as an LGBT retreat.