American history is full of interesting anecdotes and historical markers that stretch from the Atlantic to the Pacific. For fans of old pastimes as well as modern history, there’s no better way to learn about the deep cultural ties and rich traditions than through a road trip. Even if you can’t carve out the time for an extended cross-country adventure, you should still visit each of these cities for a full spectrum view of country. Whether you’re a fan of more modern metropolitan history, are swept away by the Old West era, or just love classic Americana, put down the textbooks and dive feet first into the pages of history.
From the deep South to the far North and then all the way out West, here are 15 amazing American cities with rich cultural histories to share!
1. New York City, New York
While the Big Apple may be most associated with making it big in a very modern way, the city on the Hudson has always been the great machine of America, turning out geniuses and the best and the brightest of the country. That's why it's one of the most culturally rich cities on the continent. Since the Industrial Revolution, New York City has been home to oil barons, such as Rockefeller, artists who made their way to Broadway, and all manner of writers, painters and inventors who have jazzed up, shined up, and invested in this beautiful city for generations.
No visit to NYC is complete without a walk through the expansive Central Park, a trip to the top of the Empire State Building, or passage on the Hudson to visit the Statue of Liberty. For those seeking a more alternative history, check out The Cloisters, The Brooklyn Museum of Arts, and a walk across The High Line, an incorporated park and market above the city on old train tracks.
2. Savannah, Georgia
This Southern belle is one of the few cities left relatively original since the Civil War, thanks to the surrender of the city's inhabitants at the end of Sherman's March to the Sea, which burned much of the South. Now its oak-lined streets, planned by General Oglethorpe, and blooming azaleas make it the heart of the Old South.
From brilliant eats—including shrimp and grits, biscuits and fried chicken—to spectacularly haunted houses, pubs and graveyards, a trip to the Hostess City is almost like traveling back in time. Don't forget to check out a couple of the cities curiosities as well. The birthplace of the Girl Scouts resides here, as does the church where the Christmas favorite “Jingle Bells” was written.
3. Route 66
Ok, we realize that this is less of a city and more of a cultural icon, but Route 66 is the foundation of the great move out west for family summer vacations for an entire century. Now sitting in somewhat of a revival period, Route 66 is stacked with small midwestern towns peppering the plains and the desert all the way to California. While this is definitely a trip all on its own, a trek down Route 66—from Chicago to Santa Monica—is one for the history books.
Stop in St. Louis for a chance to check out the Chain of Rocks bridge between Missouri and Illinois, or Arcadia, Oklahoma for its Pops store with over a hundred different original flavors of soda. Don’t miss the Cadillac Ranch in famous Amarillo, Texas, or Tucumcari’s famous Blue Swallow Motel in the heart of New Mexico. Not only are you riding on the road of history, but many stops along the way are perfectly reserved for the vintage feel of the original Route 66.
4. Boston, Massachusetts
When it comes to early American history, you can hardly find anywhere better than Boston. It is the home of the Boston Tea Party, the beginning of the American Revolution with the ride of Paul Revere, and the birth of the Industrial Revolution with America’s first textile mill.
For modern buffs, it also has more recent historical moments, such as Babe Ruth’s placement of the Curse of the Bambino on the Boston Red Sox and the birthplace of President John F. Kennedy. Through several revivals of the city, it’s home to a bustling metropolis, a bohemian city center vibe, and ideological center (with collegiate behemoth Harvard) that hums on the edge of modern pop culture.
5. San Francisco, California
The colorful Victorian houses in San Francisco may be famous for their prominent display in the opening of Full House, but the historical depth of the city doesn’t stop - or even begin - there. The Golden Gate Bridge, a colossal monument to art deco design that was opened in 1937, and Alcatraz, historic landmark and notorious prison of Al Capone, are just a few of the great historical visits in the city.
From the incredible cable cars to walks in the world famous Chinatown for authentic dim sum, San Francisco is buzzing with great sites and landmarks for any American history lover. Try a walk along the Fisherman’s Wharf for a great day mingling with sea lions, seafood, and museums. Check out Union Square for the cultural hub and great hangout spot in the city or the Japanese Tea Garden for a cup and a great afternoon spent among inspired flora and fauna.
6. Key West, Florida
While Key West may be most famous of the Florida Keys—thanks to Hemingway and a handful of other beach-loving artists, writers and socialites—the Florida Keys provide incredible adventure for those seeking to get an alternative history. The string of islands that stretch from the Atlantic to the Gulf of Mexico are full of unique wildlife (including the Key deer), excellent coastal diving (including trips to see famous shipwrecks) and low-key beach life.
While most travelers love to visit the Southernmost Point, it’s also a safe bet to spend a day or two adventuring to the Dry Tortugas, the US’s southernmost National Park and home to a beautiful 19th century fort. You could also catch the sunset celebration at Mallory Square with a bite of famous Key Lime goodies, and make a trip to the Ernest Hemingway House for a close look at the six-toed cats and the writer’s private study (and in-ground pool!).
7. Cherokee, North Carolina
With a rich history that spans over much of early American time, the Great Smoky Mountains are a veritable hotspot for vacationers looking to get a peek at life the way it was in the 19th century, not to mention some of the best landscape views in the country. Throughout the National Park that stretches from Cherokee, North Carolina to Gatlinburg, Tennessee, there are plenty of homesteads, mills and ruins to excite lovers of early American history.
A stop at the Museum of the Cherokee Indian in Cherokee provides a deep look at the history of the natives living in the area before, during and after the settlement of Europeans in the area. A quick look at the Mingus Mill shows how early settlers adapted to both mountain life and technology, and if you take a drive along the range to Cades Cove, you will discover the rich and sometimes difficult life of Native Americans and mountain people during the 18th and 19th centuries.
8. New Orleans, Louisiana
Briefly ruled by the Spanish after its founding in 1718 by French colonist Sieur de Bienville, New Orleans has a culturally diverse past that has come together to make it one of the most historically rich and culturally beautiful cities in America. Not only does it have greats like Bourbon Street, The French Quarter and all the excellent Creole food a person can eat, it is also home to the last battle in the War of 1812, where Andrew Jackson defeated British troops once and for all. Other memorable stops in The Big Easy include St. Louis Cathedral, the City Park, the Audubon Nature Institute and, at the right time of year, plenty of Mardis Gras festivities.
9. Santa Fe, New Mexico
While the city wasn't established until 1607, historical accounts date the Pueblo establishments typical for the area back as far as the 900s, providing plenty of resonating authenticity and making it one of the oldest cities in America. Check out the excellent architecture at the Palace of Governors, the famous stairs of the Loretto Chapel, the historical San Miguel Mission, and the Georgia O'Keeffe Museum, which boasts over 3,000 works in its permanent collection. Lucky visitors who time their trip accordingly can participate in the Santa Fe Fiesta, the oldest community celebration in our country, which started in 1712 to commemorate the Spanish reconquest of New Mexico.
10. Denver, Colorado
In the shadow of the Rocky Mountains, Denver has long been a hotspot for those looking to strap their skis on and hit the slopes, but it's also one of the largest metropolitan cities from the Old West. With 19th-century buildings, an expansive art museum, and the Cathedral of the Immaculate Conception, it's a beautiful place to catch up on some Western history, which must include a stop at the Molly Brown Mansion (made famous due its owner's survival of the Titanic disaster).
Head to Larimer Square for exquisite, high-end eats and a brilliant atmosphere or to the United States Mint for a close-up look at how our nation's money is made. Most of all, don't miss the opportunity to take day trips to Red Rocks Amphitheatre for an excellent show, Buffalo Bill's Museum and gravesite, and Dinosaur Ridge, where famous Jurassic dinosaur bones were found in 1877.
11. Bodie, California
This stop is for adventurers who love Route 66, but just didn’t get enough from the famed travel route. Known as one of America’s greatest ghost towns, Bodie no longer offers the comforts many people look for when they are on vacation, but it has a history that is too good to pass up for lovers of the Old West.
Bodie was once home to over 10,000 settlers during the Gold Rush, and was founded by Waterman S. Bodey, a settler who found a small amount of gold in nearby Mono Lake. Bodie didn't see the end of the city life until 1942, when the post office officially closed less than a hundred years after the town was settled.
With homes, churches, and shops still standing (and often, full of merchandise), this site is one for those who love ghost stories and something a little off the beaten path. Perfect for a day trip, adventurers can stay at the nearby Lake Tahoe, which is the closest city (full of the typical vacation comforts) at almost 75 miles away.
12. Seattle, Washington
Seattle’s claim to historical fame is in its more modern historical endeavors, but it has a rich history nonetheless. For lovers of grunge, Seattle is a great place to swing by and get acquainted with the favorites—Nirvana, Pearl Jam, Soundgarden, and Alice in Chains were all Seattle-born bands. The Space Needle has been a mainstay of the city skyline since 1961, taking tourists over 500 feet above the city.
The Pike Place Market is also a favorite hangout spot. Popping up in 1907, it’s one of the oldest continuously open markets in the United States and is a great place to get homegrown produce, favorite delicacies, and mingle with the locals. If you love great museums, check out the Museum of History and Industry, the Seattle Art Museum, and the Burke Museum of Natural History and Culture, which includes over 16 million artifacts.
13. Honolulu, Hawaii
Hawaii's heritage goes back much further than American history, and that's what makes it such a unique spot. From the ecological landmark of the dormant Diamond Head volcano to Iolani Palace and the home to Hawaii's last monarchs, the Oahu south shore city is home to a vibrant lifestyle and ever evolving cultural experience.
Visit the Makapuu Lighthouse Trail for fantastic views of the coastline and a bit of natural history, the various Pacific memorials commemorating Pearl Harbor, the Queen Emma Summer Palace for more Hawaiian heritage, and the Old Waialua Sugar Mill to sample some Hawaiian coffee brews, sweet treats (including locally made chocolate) and an excellent surf shop. Make sure you save plenty of time to catch the waves. Surfing is a traditional pastime of the area, it's an activity you don't want to miss!
14. San Antonio, Texas
While the Alamo is the glaringly obvious choice for any visit to San Antonio, the mission that was laid under siege in one of the most defining battles in American History is not the only great thing to love about the city, but it's certainly the highlight.
Take part in the natural history of the area with zip lining in the Natural Bridge Caverns, stop by for a tour of the Spanish Governor's 18th century palace, and make sure to reserve time (or a stay) at the Menger Hotel. The Menger Hotel is famous for an eclectic number of ghosts and as mainstay of Texan history and culture from its inception in 1859.
15. Chicago, Illinois
For fans of the gangster novels and tales of old, Chicago is the home base for the Roaring Twenties that swept through the US with a pop culture vengeance. From the Valentine's Day Massacre to the Navy Pier, Chicago's pastimes are embroiled with its future times, and any stop here is one filled with excellent stories.
Make sure to make a stop at Union Station, known for hosting over 300 trains and 10,000 people per day in its heyday. Don’t miss Wrigley Field, the home to the Chicago Clubs and opened in 1914, or any of the beaches along Lake Michigan’s shore. Chowing down on great eats such as the famous deep dish pizza, hot dogs, and cake shakes also qualify as historical sampling, so make sure you are extra hungry when you visit the Windy City!