America’s Best Kept Secrets: The 18 Oldest Towns That Have Stood the Test of Time

If you seek history when touring the US, these towns, steeped in history, offer a mix of culture, art, nature, and architecture for you to explore. From coastal delights to cultural nuggets, they’re a traveler’s treasure trove. So, if you’ve been looking for a less modern site to visit, why not consider one of these 18 towns when you’re planning your next road trip?

St. Augustine, Florida

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Founded by the Spanish in 1565, St. Augustine is a mesmerizing blend of old-world charm and Floridian beauty. As you explore the historic Castillo de San Marcos fort or wander through narrow streets lined with colonial-era buildings, it’s easy to forget you’re in the New World.

Jamestown, Virginia

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This English settlement, now preserved as a historic site, has a living-history museum that offers interactive experiences from pottery-making to soldier drills, painting a vivid picture of early colonial life.

Santa Fe, New Mexico

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Santa Fe is a fusion of cultures, with a history stretching back to 1610. The local markets burst with Native American crafts, and a culinary scene that blends indigenous flavors with modern twists.

Plymouth, Massachusetts

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Plymouth’s coastal beauty is accentuated by historic sites, including Plimoth Plantation, where reenactments bring important history to life. The town’s close bond with the neighboring Wampanoag tribe offers a unique lens into indigenous history and traditions.

New York, New York

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Before becoming the bustling metropolis we know today, Manhattan began as New Amsterdam in 1624, a Dutch trading post. Old streets like Stone Street still echo colonial designs, while, iconic structures from various eras, showcase the city’s journey from a small colony to a global capital.

Albany, New York

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New York’s capital, founded in 1614, wears its age proudly. While known for its political heartbeat, Albany is a canvas of architectural evolution, from Dutch colonial designs to English influences. Annual events like the Tulip Festival pay homage to its European roots.

Newport News, Virginia

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This city’s history flows as deeply as the James River it sits on. Established in the early 1600s, Newport News is a maritime delight. From historic shipyards to the Mariner’s Museum, the city boasts a naval legacy that’s intertwined with its modern enterprise.

Hampton, Virginia

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Founded in 1610, Hampton’s allure lies in its diverse tales. Native American heritage, pivotal Civil War events, and the birth of America’s space journey at NASA’s Langley Research Center—Hampton is where stories of resilience and innovation converge.

Portsmouth, New Hampshire

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A 1623 establishment, Portsmouth brims with New England character. The cobblestone streets, historic homes, and bustling docks all tell tales of its merchant and maritime past. Today, art festivals and local breweries infuse a contemporary spirit into its vintage setting.

Salem, Massachusetts

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While Salem is best known for its 1692 witch trials, it was also once a major global port, which is captured in historic buildings and museums. The waterfront is a testament to its seafaring past, while its artsy downtown gives a nod to the present.

Charleston, South Carolina

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Founded in 1670, Charleston oozes southern charm. Gas-lit streets wind through historic districts, with antebellum mansions, plantations and gardens, while its vibrant dining scene showcases the South’s culinary evolution.

Nantucket, Massachusetts

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This island, established in the mid-1600s, was once the whaling capital of the world. Today, Nantucket offers maritime museums filled with seafaring tales, historic lighthouses, and pristine beaches.

Dover, Delaware

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Dover celebrates its heritage with annual festivals, and features the Air Mobility Command Museum, which highlights the town’s role in aviation history. Its also renowned for the Dover International Speedway, attracting thousands of NASCAR fans yearly.

New Castle, Delaware

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New Castle’s 1651 foundation is evident in its preserved architecture. Streets echo tales of Revolutionary War heroes, while historic taverns serve as reminders of old-world hospitality. The Delaware River adds a scenic touch to this charming town.

East Hampton, New York

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The 1648-founded East Hampton’s heritage includes windmills from the 1700s, while its arts community, evident in local galleries and theaters, adds a contemporary pulse to this coastal gem.

Newport, Rhode Island

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Newport boasts Gilded Age mansions that once hosted America’s elite. These architectural marvels sit alongside contemporary music festivals, giving Newport a unique cultural scenery.

Kingston, New York

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Kingston, founded in 1652, showcases history with a twist of hip. Historic stone houses meet contemporary art hubs, illustrating the town’s journey from a Dutch settlement to a thriving cultural center.

Marblehead, Massachusetts

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Marblehead’s seafaring spirit remains undiminished, boasting colonial-era streets, historic yachts, and folklore of legendary sailors. Local regattas keep its maritime tradition alive, attracting sailors from across the globe.

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