25 of the Oldest Cities in the United States

By VacationIdea Staff on April 17, 2022 - Updated

Courtesy of SeanPavonePhoto - Fotolia.com

America’s oldest cities tell the fascinating story of the historic events that shaped the nation. As you make your way through historic districts, visiting remarkable museums, sturdy fortresses and battlefields, you will learn about the people and events that determined how we all live today. But time has not stood still and these same historic old villages and trading centers are now bustling modern cities that offer visitors a wealth of attractions, great dining experiences, and much more. Feast your eyes on some of the best art on show in the nation, visit wonderful museums and science centers and delight your taste-buds with local flavors.

We recommend that you call the attractions and restaurants ahead of your visit to confirm current opening times.

1.St. Augustine, Florida

St. Augustine 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 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. 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 in Maryland was settled over 300 years ago and is today positively bristling with African American, colonial, and maritime 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 is one of America’s oldest cities, home to a wealth of historic sites and buildings. 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 the city 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 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 the city 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 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 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 Honolulu 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 to soak up the sun and enjoy a multitude of 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 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 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.

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 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, 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.

11.New Orleans, Louisiana

In 2018 New Orleans will be 300 years old and the city will be celebrating in style with over 130 festivals to mark the occasion. The city boasts several history museums where you can get a glimpse of the many factors that have contributed to the unique ambiance of the city – highlights include the National WW II Museum, the Old US Mint, Fort Pike, and the Confederate Memorial Hall Museum. You can tour several historic New Orleans Plantations, visit a unique above-ground cemetery, ride a historic street car through Downtown and the French Quarter, or stroll through the New Orleans Besthoff Sculpture Garden. No visit would be complete without listening to some New Orleans Jazz at the Preservation Hall on Bourbon Street.

12.New York City, New York

New York, the city that never sleeps, has come a long way since it was founded on the banks of the Hudson River way back in 1624. Today New York is one of the most famous and most visited cities in the world, offering visitors an endless list of activities and attractions. Start your New York adventure by visiting the art-deco Empire State Building or One World Observatory for panoramic views of the city. After a walk or jog through Central Park you can take time out for art appreciation at MOMA (Museum of Modern Art), the Met (Metropolitan Museum), or the Whitney Museum of American Art. Other prominent city highlights include the Statue of Liberty, Times Square, and Broadway.

13.Newport, Rhode Island

Founded in 1639 by English colonizers, Newport Rhode Island is older than the US itself and has a lot of stories to tell those who choose to visit. Explore the early days of Newport by taking a walking or trolley tour of the Newport Historic District – highlights include the Newport Historical Society and the Museum of Newport History. For a break from history you can take a walk along the 3.5-mile Cliff Walk, which offers excellent ocean views and the chance to admire opulent Gilded Age mansions overlooking the sea. Petrol-heads can visit the Newport Car Museum and the Audrain Automobile Museum while art lovers can tour the Anchor Bend Glassworks and several art galleries and studios.

14.Norfolk, Virginia

Norfolk was founded in 1682, which means that you can find historic sites just about everywhere. Learn about the city’s interesting past on the self-guided Cannonball Trail History Tour, which will take you past dozens of historic buildings, homes, and monuments. You can learn about maritime history by visiting the Hampton Roads Naval Museum and see how the local residents lived hundreds of years ago on a tour of the Willoughby-Baylor House and the Moses Myers House. Outdoor recreational activities include sailing lessons, canoeing and kayaking, fishing, harbor cruising, and much more. Art lovers can immerse themselves in the vibrant arts scene at the Chrysler Museum of Art and several working art studios.

15.Pensacola, Florida

Pensacola was originally established by the Spanish in 1559, which places it squarely at the top of the list of oldest cities in the US (This fact is disputed by St. Augustine, which claims that because it has been permanently settled since 1561 it should hold the honor). Whichever way you look at it, Pensacola has around 450 years of history to share. You can learn a lot about the early years by following the Colonial Archaeological Trail, which winds through downtown Pensacola, visiting various ancient ruins and fortifications. You can also walk in the footsteps of the soldiers and settlers at Fort Pickens and visit Historic Pensacola Village. Younger visitors will enjoy the Pensacola Children’s Museum and the National Naval Aviation Museum.

16.Philadelphia, Pennsylvania

Philadelphia was established in 1682 and is often referred to as the Birthplace of the Nation because this is where the famous Declaration of Independence was signed. The city bristles with interesting historic sites that attract thousands of visitors each year. You can take a guided tour of Independence National Historical Park where you can see Independence Hall and the Liberty Bell and then move on to the Valley Forge National Historical Park. For a change of pace you can make your way to Reading Terminal Market, which claims to be America’s oldest Farmer’s Market. Art lovers can spend the afternoon at the Philadelphia Museum of Art.

17.Plymouth, Massachusetts

Settled in 1620, Plymouth has nearly 400 years of history to showcase to visitors. You can learn about the history of this modern and vibrant city by joining one of the many guided tours available; visit stately historic mansions, go on a 90-minute walking tour of downtown Plymouth, or explore the paranormal on a Ghost Tour. There are several interesting museums that document the early days – try the Pilgrim Hall Museum or Plimouth Plantation (a “living” outdoor museum). Art lovers have many art centers, galleries, and studios to visit, and the city offers cranberry picking (seasonal), farmers markets, and brewery tours for all the foodies.

18.Salem, Massachusetts

Salem was founded in 1626 and is named after the Hebrew word for peace. However, the history of the city is anything but peaceful, and Salem is primarily famous for its association with witches and witchcraft. Learn all about the notorious Salem Witch Trials by watching “The True 1692” film at Cinema Salem at the Museum Place Mall and follow it up by joining one of the enormously entertaining Ghost Tours that are offered by day or night. You can visit the ghoulish Frankenstein’s Castle Wax Museum is you dare, or, on a lighter note, pay a visit to the Derby Wharf Light Station or the New England Pirate Museum.

19.San Antonio, Texas

Established as a Spanish mission in 1718, San Antonio is the oldest city in Texas and has grown into a prosperous and interesting modern city. At the San Antonio Missions National Historical Park (a UNESCO World Heritage Site) you can learn about life in the missions during the 1700s as you tour four historic Spanish Missions on a free guided tour. For some adrenalin-boosting excitement you can visit Six Flags Fiesta Texas, which combines exhilarating rides and shows, have fun at SeaWorld San Antonio, or cool off at one of several water parks. Do not leave the city without strolling along the fabulous River Walk and taking the kids to the DoSeum Children’s Museum.

20.San Francisco, California

Another of America’s oldest cities, beautiful San Francisco was established way back in 1776 and is named after St. Francis of Assisi. Today the city offers visitors a kaleidoscope of interesting attractions and activities. A good place to soak up the atmosphere (and get great views of the famous Golden Gate Bridge, Alcatraz, and the city skyline) is Pier 39 at Fisherman’s Wharf – while you are there you can visit the excellent Aquarium of the Bay. No visit would be complete without walking across the remarkable Golden Gate Bridge and touring the notorious Alcatraz prison. The San Francisco Museum of Modern Art will mesmerize art lovers, and there are many museums to suit all interests.

21.Santa Fe, New Mexico

Established by the Spanish in 1607, Santa Fe is one of the oldest cities in the US and has over 400 years of history to showcase. There are several historic districts to explore and many historic sites to visit, including several well-preserved Indian Pueblos, the Palace of Governors, and the San Miguel Mission, which is the oldest church in the US. If you are not sure where to start you can join one of the many guided tours available – choose from history tours, art and architecture tours, ghost tours, food tours, and even wine tours. There are also a host of outdoor activities to enjoy in and around the city including hiking, biking, river rafting, and much more.

22.Savannah, Georgia

Dating back to 1733, Savannah is one of the US’s oldest and loveliest cities and was once the State Capitol of Georgia. Savannah is an ideal city to explore on foot either at your own pace or by joining a guided tour of Downtown Savannah – there are several walking tours to choose from including an architectural tour. As you make your way through the city squares you will see historic mansions, opulent theaters and commanding churches as well as a good selection of museums. If you feel a little lazy you can hop aboard a bus or trolley tour instead. In addition to sight-seeing, visitors can also enjoy the beach, go kayaking at Palmetto Bluff, or enjoy a scenic riverboat cruise.

23.Albany, New York

Originally settled by the Dutch more than 400 years ago, the small settlement has grown by leaps and bounds to become the capital city of New York State. History buffs and architecture enthusiasts are in for a treat as they admire some of America’s oldest and grandest buildings, which stand shoulder to shoulder with modern monuments like the Egg (performing arts center) and the Empire State Plaza. No visit would be complete without touring the elaborate New York State Capitol Building (1867 -1899) to see the famous Million Dollar Staircase, Senate Room, and War Room. Art lovers can visit the Palace Theater, Times Union Center, and The Egg. The city also offers several excellent museums, good dining, and much more.

24.Washington DC

Washington was established as the national capital by President George Washington in 1790 and is without doubt one of the US’s most interesting and beautiful historic cities with activities and attractions for everyone. You can delve into Washington’s history and heritage as you visit the Smithsonian National Museum of American History, tour the State Capitol Building, and admire the brilliant neo-classical architecture of the Jefferson Memorial. You would need months in the city to properly explore all the world-renowned Smithsonian museums, see the 9/11 Pentagon Memorial, and visit Arlington National Cemetery, so it is important to carefully plan your visit. A guided tour of the highlights is recommended if you only have a limited amount of time in the city.

25.Williamsburg, Virginia

Founded in 1638, Williamsburg played a pivotal role in the Revolutionary War and you can learn about almost four centuries of American history as you tour the greater Williamsburg area. At Colonial Williamsburg you can watch a re-enactment of the events that led up to the Revolutionary War and then travel on to Yorktown Battlefield where you can stand on the exact spot where the British army surrendered, paving the way for American independence. Besides a host of historic sites and museums Williamsburg also has a lot of fun attractions including brilliant theme parks, scenic hiking/walking trails, art galleries, wineries, and breweries.