Rumored to be the famed pirate's lookout tower, this historic stone structure is now just watching for tourists.

A school used as a model for public education across the country.

The tomb of Increase Mather and his son Cotton, influential colonial ministers obsessed with the occult.

This nearly 200-year-old restaurant's history includes an exiled French prince, JFK, and a very hungry Daniel Webster.

What was once a true peninsula has now been filled in, causing the water to recede and leaving many streetside "waterfronts" and landlocked "islands."

Millions of numbers carved in glass represent the tattoos forced upon victims.

A centuries-old church stands as a testament to Boston's "father of architecture."

Silverware in the sidewalk outside a grocery store cements this neighborhood’s Italian culinary history.

This historic patch of real estate offers a glimpse of colonial Boston.

An interesting decoration on this historic site, this weathervane comes with as many legends as it does questions.

This popular Boston haunt is reminiscent of a time gone by, when slow cafes and sweet-smelling smoke wafting from patios was the norm.

Statue commemorating the use of ether in anesthesia.

One of the indelible moments of the American Revolution took place at this location.

A former waterfront market is now in the center of town due to some interesting Boston engineering.

A mysterious stone embedded at the base of a historic Boston building.

Shelves covered in dozens of coffee bean varieties fill this North End institution.

Mrs. Mallard and her brood are a beloved fixture in Boston Public Garden.

The site of Paul Revere's historic two lantern warning.

The American Revolution was galvanized into serious action due to the tragic clash with British soldiers that occurred at this location.

The Boston square dedicated to the dark poet who was born nearby.

This area was once known for being a lawless haven for rough-and-tumble sailors, earning the maritime-themed nickname "the black sea."

"Mock all and sundry things, but leave the saints alone."

This ambitious father and son team reigned supreme over the North End, and witches, for many years.

Tragedy on Little Brewster Island memorialized.