Macabre headstones carved with winged skulls, dancing skeletons, and pithy reminders of impending death.

The remnants of a Gilded Age elegance preserved in the middle of a stark modern tower.

The history of the tea trade is told in bas-relief on this historic pair of Boston doors.

American revolutionaries and British soldiers alike are buried here in the fourth-ever cemetery in Boston.

One of the oldest used bookstores in the U.S. has been selling antiquarian treasures since 1825.

The former site of an all-but-forgotten colonial landmark is now remembered by an often overlooked bas relief.

Museum dedicated to awful artwork.

Rising 30 feet in the air atop Quarry Hill, the Old Powder House is the oldest stone building in the state of Massachusetts.

An alley way dedicated to graffiti and street art is a constantly changing street gallery.

This upscale streetwear store is hidden behind a fake Snapple machine in the back of a deli.

A beautiful Victorian-era cemetery, complete with a miniature village.

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

The celebrated eyesore created by starry-eyed sweethearts.

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

A men’s restroom became a sandwich shop.

Ice cream stand, snack bar, and time capsule of milk conveyance.

On a former island, this old fortification once used to protect the Boston Area and started Edgar Allan Poe in his military career.

This popular tourist cave was ignored for almost 200 years before being mined into an attraction.

The vast, legendary catacombs hold secrets much stranger than stacked bones.

An eccentric inventor's castle home with its own indoor weather system.