The Oldest Cities in the United States

1. St. Augustine, Florida

St. Augustine, Florida was established in 1561 and because it has been permanently inhabited since that date is has the distinction of being considered the oldest city in the United States.

Visitors can learn about over 450 years of history as they explore a plethora of historic sites, including Fort Matanzas, Castillo de San Marcos (the oldest masonry fort in the US), the Colonial Quarter, and a long list of other fascinating historic buildings and museums. There are many great places to stay in St. Augustine. You can see many of the sights on an Old Town Trolley Tour or a Ripley’s Red Train Tour. For a change from history you can go on a scenic schooner cruise, visit the Marineland Dolphin Adventure, or take a ride on a bi-plane.

2. Annapolis, Maryland

The delightful coastal town of Annapolis, Maryland was settled over 300 years ago and is today positively bristling with history. To get a glimpse of the pioneer days in Annapolis you can visit the Maryland State House, the Bannekar-Douglass Museum of African American Heritage, and the Annapolis Maritime Museum.

If you love historic houses you should not miss the well-preserved William Packer House and Gardens and the Charles Carroll House and Gardens.

For an unusual perspective of the city you can take a Chesapeake Bay Cruise and pay a visit to the Thomas Point Shoal Lighthouse. The city is very easily explored on foot via either a guided or self-guided walking tour.

3. Boston, Massachusetts

Founded back in 1630 by Puritan colonists from England, Boston, Massachusetts is one of America’s oldest cities, home to a wealth of historic sites and buildings the whole family will enjoy. Boston played a vital role in the American Revolution, and history buffs can follow in the footsteps of early revolutionaries as you walk the famous Freedom Trail, which will take you to see 16 historic sites.

You can join a guided tour, or follow the interpretive trail at your own pace. Other must-see attractions in Boston include the Kennedy Presidential Museum, the Boston Tea Party Ships and several historic districts packed with wonderful old buildings.

For a break from history you can take a stroll through some beautiful gardens, enjoy great shopping, and round off your day with a wonderful fresh lobster dinner.

4. Charleston, South Carolina

The glorious modern city of Charleston, South Carolina was originally settled by British colonists in 1670 and was a leading center for agriculture and economy until the start of the Civil War in 1861. Today Charleston contains a treasure trove of important historic buildings that date back to pre-Civil War times – history buffs will need to prioritize their time to explore all 24 historic sites in the city. You can explore on foot by joining a walking tour or do it the easier way on a horse-drawn carriage tour.

Besides visiting the exact spot where the Civil War broke out at Fort Sumter, you can visit numerous excellent museums that showcase the varied history of this fascinating city.

5. Detroit, Michigan

Another of the US’s oldest cities, Detroit, Michigan was founded in 1701 by the French colonist Antoine de la Mothe Cadillac. From humble beginnings as a fur trading post, Detroit grew by leaps and bounds to become the fourth-largest city in the US by 1920. Much of the city’s growth was due to the automotive industry, and today you can visit several interesting museums and historic sites in Detroit that pay homage to the city’s past. Highlights include the Automotive Hall of Fame, the Ford Piquette Avenue Plant, the Edsel and Eleanor Ford House, and the Henry Ford Museum. When you need a break from historic automobiles you can visit the Detroit Institute of Arts and MOCAD (Museum of Contemporary Art Detroit).

6. Honolulu, Hawaii

Although the island of Oahu in Hawaii has been populated for many hundreds of years it only became a US colony when it was annexed by the US in 1898. Originally a modest village, the city became a prosperous trading center and later a vital US military post.

Today most visitors come to Honolulu, Hawaii to soak up the sun and enjoy scenic beaches, adventure sports, but if you are interested in learning more about the often-turbulent history of the island you can visit several historic sites including Pearl Harbor, Iolani Palace, and Kilohana Plantation Estate. Other interesting historic sites include Hulihee Summer Palace and Puuhonua o Honaunau National Historic Park.

7. Jersey City, New Jersey

Jersey City, New Jersey dates back to the 1630s, which firmly places it on the list of contenders for the oldest cities in the US.

Originally a fur-trading settlement on the Hudson River, the city played a vital role in welcoming thousands of immigrants to the US during the nineteenth century when all new arrivals were processed through near-by Ellis Island.

Today you can visit Liberty Park for wonderful views of the Manhattan Skyline, the Statue of Liberty, and Ellis Island. There are also several historic sites to visit including the 1917 William Trent House Museum, the American Labor Museum, and the Battleship New Jersey from WW II. Children will love the fascinating Liberty Science Center.

8. Lexington, Kentucky

Lexington, Kentucky was established in 1775 in the fertile Bluegrass Region that provided a rich hunting ground for Native American Tribes. By 1820 Lexington was the wealthiest and most prominent city in the state, and today visitors can look forward to an enriching vacation in one of America’s oldest cities. Also known as the horse capital of the world, Lexington is an exciting destination for horse lovers – you can see over 50 breeds of horses at the Kentucky Horse Park or join a Horse Park Tour.

History lovers will want to head to the Shaker Village of Pleasant Hill to see a reconstructed Shaker settlement, while gourmands can visit several wineries, explore the Brewgrass Trail of breweries, and sample delectable cuisine in the city’s vibrant Downtown. Map

9. Memphis, Tennessee

World famous as the Home of Rock ‘n Roll and the Birthplace of the Blues, it may surprise you to know that Memphis, Tennessee is also one of America’s oldest cities, founded in 1819.

There are several historic districts where you can see some of the original buildings, but most people visit Memphis on a musical pilgrimage to see the actual recording studio at Sun Studios (1950) where Elvis started his epic musical career.

Besides a nostalgic studio tour, music lovers can also tour his elegant Graceland Mansion. Other music-related attractions include the Memphis Rock and Soul Museum and the Blues Hall of Fame. To experience the essence of the city you can visit some of the blues clubs on Beale Street or attend an outdoor concert.

10. Mobile, Alabama

Founded in 1702, Mobile is the oldest city in Alabama and one of the oldest in the US. Everywhere you turn you are surrounded by history; a good place to start your tour of the city would be the History Museum of Mobile, which will give you a great introduction to the other historic attractions.

You can explore the famous African American Heritage Trail (which includes no less than 40 historic sites), get a glimpse of even earlier times at the University of South Alabama Archaeology Museum, stroll through historic downtown Mobile, or tour the Phoenix Fire Museum and the Mobile Medical Museum. For a break from history you can spend a few fascinating hours at the Gulf Coast Exploreum Science Center.