A nearly 100-year-old dining car in upstate New York embodies the golden age of roadside dining.

An enormous cat made of recycled wood scraps.

The schoolhouse where Jesse Merwin, the inspiration for the "The Legend of Sleepy Hollow" character, once taught.

The former residence of Elizabeth “Mumbet” Freeman, an enslaved African-American woman who successfully sued for her freedom.

Herman Melville wrote 'Moby Dick' in this landmark 18th-century house surrounded by farmland.

The mansion home of author Edith Wharton.

Eight whimsical acres of metal art.

Breathtakingly blue walls shimmer inside the "Glacier Behind the Town."

Upside-down trees serve as natural flower pots in this hanging garden of Alaska.

Maine's oldest diner also happens to win acclaim for its elevated comfort food.

Walk the same tracks that once ferried Gilded Age aristocrats to their vacation destinations.

This architectural onion has an original 1930's Jerry O'Mahony dining car at its core.

Eclectic collections, artwork, and some feline friends fill the writer's former home.

Books you don’t need in a place you can’t find.

This small shop walked so America could run on Dunkin'.

The nation's second-ever First Lady urged the founding fathers to "remember the ladies."

This art display in Dedham honors a local fish, and is dedicated to the volunteers who restored the canal.

This tower pays homage to a legendary Viking fort established in Massachusetts that never really existed.

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

The first bell ever cast in Boston was cast by Paul Revere...and sounded terrible.

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

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

One woman’s obsession gave birth to this lovely oddity at the Boston Public Library.

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