21 Best Road Trips for History Buffs

Ralph Waldo Emerson said that it’s the journey, not the destination. Why belittle the destination, though, for the sake of the journey? I say it’s…


Ralph Waldo Emerson said that it’s the journey, not the destination. Why belittle the destination, though, for the sake of the journey? I say it’s the entire road trip, from start to finish. Moreover, for the history buffs, it’s the little stories behind the stops and destination. 

America is packed with historical landmarks, expansive highways, and pristine beaches, making it difficult to decide where to begin exploring. To serve as your guide, here are some historical road trips that can take you on a journey to the past. 

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1. Pacific Coast Highway (California)

Traffic on Pacific Highway Coast at night in California MSN
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The Pacific Coast Highway tracks the California coast from San Francisco to San Diego. You can enjoy stress-free, traffic-free driving from north to south while taking in the ocean view for the entire trip. It offers a fun experience in California’s rich history and culture. 

Start from Seattle and cruise towards Santa Cruz, Monterey Bay, and Big Sur for a complete trip. Visit the California State Historic Park and climb Point Sur, a lighthouse with an amazing view of the mountains and the ocean. From there, visit Hearst Castle, the Danish Capital of America, Solvang, and the Malibu Pier. 

2. New Orleans (Louisiana)

Baton Rouge Bridge Over Mississippi River in Louisiana MSN
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A road trip to New Orleans, known as The Big Easy and Crescent City, screams Cajun and music. Visit Bourbon Street and Jackson Square in the French Quarter to explore the rich history of jazz and how music has shaped this city.

Immerse yourself in New Orleans during Mardi Gras (typically held in February or early March) for the ultimate experience. This world-famous celebration explodes with vibrant parades, elaborate costumes, and infectious music. Mardi Gras offers a unique window into the city’s rich cultural heritage and celebratory spirit.

3. Boston (Massachusetts)

Bunker Hill Monument MSN
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Known as the historic northeast city, Boston houses some of the first structures built in the country, including Boston Latin School, the first public school. Go on a road trip and explore different historical periods by following the Freedom Trail, a 2.5-mile road winding past 17 historical landmarks.

You can also drop by the Boston Common, see the exhibits at the JFK Presidential Library, and get a glimpse of the original chest from the 1773 Boston Tea Party.

4. Route 61

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Route 61, or Blues Highway, stretches from Nashville to New Orleans. It’s the perfect road trip for music fans. This 816-mile musical odyssey takes you from the birthplace of Rock ‘n’ Roll in Memphis to the cradle of Jazz in New Orleans.

5. Park City (Utah)

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Utah’s Park City is a paradise for skiers and snow fanatics. Get in your car to visit the Park City Mountain Resort for a comprehensive ski tour, or join a Ghost Tour for chilling stories of the past. Check out the Park City Museum, too, for an in-depth knowledge of the history of the early settlers. 

If you’re looking for a place to stay, you might like the Washington School House or the Blue Church Lodge, depending on your budget. While both are listed on the National Historic Register, their price points vary. 

6. Key West (Florida)

Duval Street on Key West, Florida MSN
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Key West takes pride in the historical sites littered all over the island. Old Town in Dixie County houses stunning 19th-century homes in complex little streets. Visit The Truman Little White House to learn the history of the 33rd President of the United States, Harry S. Truman.

For ocean tales of survival, visit the Key West Shipwreck Treasure Museum. You’ll witness salvaged treasures, including the Isaac Allerton, a merchant vessel from the late 1800s. 

7. New York to Boston

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For a complete historical travel experience, consider the New York to Boston (and vice versa) road trip, passing by I-95 and I-91, respectively. The entire trip can take as fast as 4 hours if you’re off to go straight without added stops and side trips.

Visit Rhode Island’s Providence on your way to Boston and check out the Governor Stephen Hopkins House, a museum about Stephen Hopkins, the governor who was involved in the signing of the Declaration of Independence. 

8. Gateway (Colorado)

Palisade at Gateway Colorado MSN
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Gateway in Colorado is the perfect road trip destination for geology experts and rock fanatics. In the west, enjoy the sight of the desert and the scattered rock formations, as well as preserved dinosaur tracks to marvel at. 

Join the hikes in the red-rock canyons, which are already 300 years old. You can also cruise through the bike trails that stretch 26 miles across the town. 

9. Nashville (Tennessee)

Belle Mead Plantation in Nashville MSN
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Nashville offers some of the most bitter remembrances of the dark times in American history it will make an interesting road trip to take. Belle Meade Plantation, an 1853 Greek-style mansion, was known to benefit from enslaved labor. Today, it’s a historical attraction widely known for its onsite restaurant and winery. 

The city also features the Tennessee State Capitol and the monuments of Andrew Jackson and Andrew Johnson, the 7th and 17th presidents of the United States, respectively. Designed by popular architect William Strickland, these structures boast a Greek Revival style that’s amazing to look at. 

10. Route 66

Route 66 in New Mexico, USA MSN
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Route 66 stretches 2,500 miles in Midwest America, making it a legendary road from Chicago to Los Angeles. It passes through several American states, including Arizona, New Mexico, Missouri, and Illinois. 

With so many states to pass through, you’ll notice abandoned establishments, from motels to diners, on this road trip. The view of this route seems to be lost in time, along with multiple abandoned towns like Calico, Hackberry, and Glenrio.  

11. Rochester (New York)

Rochester New York at night MSN
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Rochester is the home of Women’s Rights history and registers the success of establishing women’s rights over a century ago. Go on a road trip all over the city to dive deeper into this part of the country’s history. The city even facilitates early women’s rights gatherings and seminars you can explore. 

The home to activist Susan B. Anthony, Rochester also houses the National Museum and House that carries her name. It was the center of the civil rights movement in 1872, and you’ll see the stories buried and displayed on this historical site. 

12. San Antonio (Texas)

Cityscape of downtown San Antonio in Texas MSN
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For a road trip to San Antonio, Texas, expect a rollercoaster of stories buried in the past. Learn more about the Battle of the Alamo and how this event affected the conclusion of the Texas Revolution. 

The then-fortress witnessed the 13-day siege of the Texian soldiers against a much bigger Mexican army in 1836. Before it was a fortress, though, it served as a colonial outpost for the Spanish empire in 1718. 

13. Blue Ridge Parkway (Virginia)

Mabry Mill in Blue Ridge Parkway MSN
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The Blue Ridge Parkway in Virginia stretches 469 miles from Virginia to North Carolina. The road trip will include 29 counties in total from both of these states. 

The road passes through several American national parks, including the Great Smoky Mountains National Park and the Shenandoah National Park. Enjoy the view of the mountains at these sites and the history behind them. You can also drop by Asheville’s city center. 

14. Healdsburg (California)

Vineyard in Sonoma California MSN
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California’s Healdsburg has a fascinating history connected to the 1920 prune farming and winemaking. It takes pride in its magnificent vineyards, which produce delicious wines. If you’re fond of grapes and wine, go on a road trip to this city for a unique experience.

Visit the Harmon Guest House, a 39-room structure that promotes Sonoma County Hills. You may also consider Hotel Healdsburg if you like hiking and trails. 

15. Savannah (Georgia)

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Savannah features the first-ever African Baptist Church, also considered North America’s oldest operating African-American congregation. When on your road trip to this city, drop by the Davenport House Museum to look at the Renaissance architectural style. 

To enjoy history in nature’s setting, consider checking out Wormsloe State Historic Site and Forsyth Park. The former houses a tabby ruin where the first group of English settlers stayed, while the latter offers a stunning aesthetic through the 1850 structures. 

16. Outer Banks (North Carolina)

The Bodie Lighthouse MSN
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Outer Banks offers a 138-mile road trip with scenic views. The Wright Brothers National Memorial provides details on the popular brothers and innovators.

If you’re an ocean lover, visit the Bodie Island Lighthouse. The 156-foot structure is the third successful lighthouse construction after being destroyed during the 1861 Civil War. 

17. Baltimore (Maryland)

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Baltimore is the center of American literature, featuring the homes of literary geniuses like Gertrude Stein and Frederick Douglas. If you’re a fan of Edgar Allan Poe, go on a road trip and visit the Edgar Allan Poe House and Museum for a more in-depth look at his life.

Walk through the Waterfront Promenade, a seven-mile road from Fort McHenry to Canton Waterfront Park. Fort McHenry played a huge role in the War of 1812 when soldiers successfully defended it from the British Navy in 1814.

18. San Diego (California)

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California’s San Diego offers a remembrance of the Mexican-American War in the 1850s and the Gold Rush that followed. The city is also known for its innovation, with technology labs and developers at the forefront.

In your San Diego road trip, include a visit to Old Town San Diego State Park, a state-protected historical park in the city featuring historical buildings dating from 1820 to 1870. For a sign of Spanish influence in the city, visit the Mission Basilica San Diego de Alcala, a Franciscan mission founded in 1769. 

19. US Route 101 (Oregon)

Yaquina Bay Bridge in Newport Oregon, along US Highway 101 MSN
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Also known as the Oregon Coast Highway, US Route 101 displays a stunning view of the Pacific shoreline. The 363-mile road stretches from northern Oregon to the South in only 8 hours of driving. 

Stop by Fort Astoria and learn the history behind John Jacob Astor’s Pacific Fur Company and its production of beaver pelts. On your way to the fort, admire the rustic charm of the Victorian homes along the road. 

20. St. Augustine (Florida)

St. Augustine Shopping Street MSN
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Considered the oldest city in the country, St. Augustine also holds the oldest fort and schoolhouse, which is the Castillo de San Marcos. It acts as a protection for the Atlantic trade route and a proof of the Spanish occupation in Florida. Going on a road trip to this city gives you a stunning visual of the remembrance of this city under Spain.

The Augustine Lighthouse and Maritime Museum, with its 165-foot height above sea level, offers a stunning view of the water. This 1500-made structure started as the first wooden watch tower before its restoration in 1871. 

21. Newport (Rhode Island)

Historic District in Ocean Drive Newport MSN
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Explore Rhode Island’s Newport in just ten miles as you cruise through the coast of Aquidneck Island. Known as the “Ten-Mile Drive,” this road trip takes you to iconic historical landmarks, including Ocean Drive, Fort Adams State Park, and Gilded Age manors like The Breakers, Chateau-sur-Mer, and The Elms. 

These mansions offer a peek at the Gilded Age, which lasted from the 1870s to the 1890s. During this time, wealth inequality and corruption reigned supreme. Each mansion bears witness to the dark tales behind its luxurious walls and pillars.

Mysteries, Mountains, and Mouthwatering Delights: The Unbelievable Cameron Highlands Resort Getaway

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Cameron Highlands is known as a little piece of England in Asia. It has a cool climate with beautiful green hills and tea plantations, perfect for relaxing walks, golfing, and relaxing afternoon tea. 

The rooms at the Cameron Highlands Resort are spacious and have a classic colonial design that feels elegant and welcoming. There are 56 well-appointed rooms and suites, all with a fantastic view of the golf course and the beautiful hills and green forest in the background. It’s a wonderful place to stay and enjoy the natural beauty of Cameron Highlands.

15 Road Trip Hacks You Need, According to Seasoned Travelers

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Looking for the best road trip hacks for your upcoming adventure? Road trips are immensely enjoyable, but they can quickly turn into a drag if you don’t get enough sleep, fail to pack the right snacks, encounter dirty restrooms, or lose network coverage. Proper planning and preparation are key to ensuring a successful journey. Check out these awesome hacks:

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