Places JaySky Wants to Go

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

Like stepping into a spooky fairy-tale, this shop carries the dark ideas of artists and other makers.

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

Site of a famous 19th-century transcendentalist utopian community, now abandoned.

Over 50 whirling pools left behind from the glacial age.

This former Masonic hall has been turned into an art project that uses even more metaphysical iconography.

Unlike other abandoned asylums this empty institution welcomes visitors, just don't go in the buildings.

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

One of the now-less-hidden floral gems of the "Emerald Necklace."

Friction between grains of sand cause a curious "singing" sound.

19th-century operating theatre in which the use of ether was first demonstrated - plus, a skeleton and a mummy!

No one really knows how these old hobby horses got here, but the herd keeps growing.

The walkable ruins of an 19th century hotel, destroyed in a horse cremation gone wrong.

The often-overlooked ruins of one of the first buildings designed by famous landscape architect Frederick Olmsted.

One of the most scenic falls in Massachusetts has a history of death and grim legend.

Museum dedicated to awful artwork.

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

Ralph Waldo Emerson spent two years living here decades before it became a Frederick Law Olmsted-designed park.

Enjoy an overnight at an old haunted B&B site of the Borden family murders.

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

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

This abandoned bootleg attraction was built to cash in on the popularity of classic TV show, F Troop.

This curiosity shop contains a museum filled with bizarre, unique objects.

Outsider Art Community.