A crumbling hospital from the 1850s on Roosevelt Island.

This peaceful Massachusetts graveyard was one of the first "garden-style" cemeteries in America.

The oldest playground in America.

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

Berthed at the Charlestown Navy Yard in Boston, "Old Ironsides" is the oldest commissioned warship still afloat.

An easy-to-miss garden in Boston's North End honors the mother of JFK and others who lost children in WWII.

This monument on Breed's Hill proves that one of the most famous battles of the Revolutionary War is misnamed.

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

The oldest working bell set in North America, the bells at Old North Church sat silent for their first four years in Massachusetts.

Impossibly life-like natural history models created out of glass by a father and son.

The site of one of the strangest disasters in history—a wave of deadly molasses traveling at 35 mph.

The oldest Italian café in Boston, this spot also serves as a veritable museum of vintage coffee ephemera.

Three prestigious academic collections come together to create a world-class natural history museum.

This cemetery served as the only official burial grounds in Cambridge for nearly 200 years.

This "life-size" depiction of Mickey Mouse as a half-lobster is both whimsical and a bit creepy, standing guard over the Boston waterfront.

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

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

This massive tea kettle was once a promotional stunt for the Oriental Teashop.

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

No one messes with the Massachusetts sacred cod, not this time...

A men’s restroom became a sandwich shop.

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

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

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