The high ground at the eastern end of the Portland peninsula. Long the city's working-class neighbourhood, in the last decade it has gentrified hard — but the steep cross streets, clapboard triple-deckers, and views over both Casco Bay and Back Cove are unchanged. The Portland Observatory crowns the top of the hill.
Walk up Congress Street from the Old Port for the easiest grade. Side streets like Vesper, Atlantic, and St. Lawrence are worth a wander for the architecture. End at the Eastern Promenade for the view.