Timeless Saunter in the Eternal Black Rock Historic District, CT

This old-timer, the Black Rock Historic District, dates all the way back to 1644, even before the classy city of Bridgeport came about in 1821. By the 1760s, it was the Connecticut version of Downtown Abbey, a go-to for shipping, trading, and all-round liveliness – one of the top three hotspots during the American Revolutionary War. Its prime position kept it hopping until the 19th century, when it gave a little and started merging with Bridgeport's streets. A fair few of the original buildings are still standing tall, thanks to good ol' preservation efforts. So, let's take a nosey.

Sources: Wikipedia, OpenStreetMap, Wikidata, Wikimedia Commons