With gorgeous Victorian-style buildings, Portland has been rebuilt three times and has a long, transformative history through various conflicts in America’s past.

Portland, Maine

The Portland Observatory is a tower fitted with a telescope that used to alert the town when ships were approaching. It is the country's only known remaining building of its kind.

Try aligning your trip with one of the events by the Old Souls, an association of history lovers with a passion for preservation, to connect to knowledgeable locals.

This resort town boasts a 100-year-old amusement park on the beach and a late 19th-century pier with seafood restaurants, bars, and a carousel.

Old Orchard Beach, Maine

Montpelier's Vermont State House is a Greek-inspired, gold-domed building filled with history, art, and interior-preserved architecture.

Montpelier, Vermont

Stop by the Vermont Historical Society Museum, as it has historical artifacts and covers every significant happening in the state's history since being settled by colonizers.

Portsmouth is a city well-balanced in culture, history, and beauty. The brick streets lead you to historic mansions, churches, and a submarine-turned-maritime museum.

Portsmouth, New Hampshire

Visit 18th-century Georgian mansions like the Wentworth-Gardner House or Moffatt-Ladd House. The town’s St. John's Episcopal Church has the country's oldest playable pipe organ.

Thanks to Yale University, New Haven is one of New England's most prestigious and historically significant cities with landmarks, libraries, and museums.

New Haven, Connecticut

Learn about world history at Yale Peabody Museum. The Yale Art Gallery and the Morris Steinert Collection of Musical Instruments both focus on art history.

Check out the Divinity Library, Cushing/Whitney Medical Library, or the Beinecke Library for an intriguing knowledge overload with rotating exhibits and niche topics.