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30 Best Underrated Historic Towns East of the Mississippi


The region east of the Mississippi is where the United States was born, and as such is chock-full of historical hotspots. But while everyone knows about places like Philadelphia and Boston, who has heard of Norris or Christiana? Marblehead?

On this list are 30 of the best underrated historic towns east of the Mississippi River. Their claims to fame are varied — one of them was created to produce bombs as part of the Manhattan Project, while another boasts an ancient downtown complete with “pirate alleys” — but all of them share fascinating historical stories and significance that are sure to thrill any visitor.

Abingdon, Virginia

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From hiking to shopping, sweet Abingdon, Virginia has something to offer just about anybody. Abingdon’s Main Street is the perfect place to spend some time wandering. Window shop the many art galleries, or pop into a boutique or antique store for some unique purchasing opportunities. Historians and hikers will get a kick out of the Creeper Trail, a 34.5-mile trail that follows what was once a working train line.

Bardstown, Kentucky

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Bardstown, Kentucky is a sweet and historic little town that is listed on the National Register of Historic Places. First settled in 1780, Bardstown is most famous as the location of “My Old Kentucky Home” and a spot on the Bourbon Trail (Jim Beam and Makers Mark are both just down the road). The picture-perfect downtown area is lined with old buildings done in the Georgian and Federal styles, and gems include the Nelson County Jail, Old L & N Station, and the Talbott Tavern, the latter of which has a jaw-dropping history of its own (stop in for a bite to eat, and ask the host for a list of Talbott Tavern historical events — you won’t be disappointed!).

Bath, Maine

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Bath, located on the shores of the Kennebec River, has long been known as the “City of Ships.” Its walkable and inviting downtown is lined with historic brick buildings housing shops, restaurants, and bakeries, then ends at dry docks and shipping cranes, providing glimpses into Bath’s important shipbuilding past. While in town, be sure to stop by the Maine Maritime Museum, which offers an entertaining overview of the town’s shipbuilding history from wood to steel.

Berlin, Maryland

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Berlin, Maryland makes our list of the best underrated historic towns east of the Mississippi not because it was the locale of any major historical event (though it’s history surely isn’t anything to sneeze at), but because of its many annual traditions that celebrate the past. Berlin’s picturesque downtown, which has been a main filming location for movies like Tuck Everlasting and Runaway Bride, hosts a number of events throughout the year including bathtub races, the Fiddlers’ Convention, and the famous Victorian Christmas, during which the whole town dresses up and carries on the traditions of Christmases past.

Cherokee, North Carolina

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Cherokee, North Carolina — located a hop, skimp, and jump away from the popular Smoky Mountains — is home to the Museum of The Cherokee Indians. This fascinating place is worth a visit for anyone set on understanding the American story. The museum’s impressive collection includes hundreds of genuine artifacts, plus a 20-foot hand-carved redwood statue of Sequoyah, the Cherokee who documented the Cherokee language for future generations. Also in town is the Oconaluftee Indian Village, an authentic working village that offers hands-on activities and demonstrations to teach visitors about what life was like as a Cherokee during the 1760s.

Christiana, Pennsylvania

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Though you may have never heard of it, Christiana, Pennsylvania was a major catalyst for what would become the Civil War. In 1850, the Fugitive Slave Law made it illegal to harbor runaway slaves, and when one wealthy landowner discovered some of his slaves had escaped, he hunted and found them in the house of his neighbor, who happened to be an abolitionist. The subsequent battle between the two gained nationwide attention, and served to highlight just how divisive of an issue slavery was. Today, visitors to Christiana can visit the fascinating Underground Railroad Center to learn how local homes, hotels, the railroad depot, town post office, and even jail were used to transport slaves to freedom.

Clinton, Tennessee

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Clinton, Tennessee, located near Oak Ridge, another underrated historic town on our list, was the site of the very first integrated high school in the United States. Families, and especially children, will enjoy learning about this momentous historical event at the Green McAdoo Cultural Center, which has a fascinating exhibit that shows just how these turbulent events occurred and what the reactions were in this small town.

Cranbury, New Jersey

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Located in central New Jersey and surrounded by big modern cities is Cranbury, an historic small town that can trace its history all the way back to 1698. At least, that’s the year Cranbury’s oldest buildings were built. To really get a feel for this cool little town, head straight to the Cranbury Museum and pick up a self-guided walking tour. You’ll walk past 31 interesting sites in all, including the Cranberry Inn (built in 1800 and the town’s oldest business), the Town Hall, and Brainerd Cemetery, the latter of which has more than 40 graves that are pre-1800, plus more than 80 Revolutionary War veterans.

Dahlonega, Georgia

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California may be the Golden State, but the first gold rush actually took place here, in Dahlonega, Georgia. Located just an hour north of Atlanta, Dahlonega is a beautifully mountainous small town complete with beautiful architecture, hikes that lead to waterfalls, dozens of wineries, and a packed calendar of fun community events.

Fredericksburg, Virginia

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Thousands of tourists flock to places like Washington, D.C., Richmond, and Charlottesville each year, but nearby is Fredericksburg, one of our 30 best underrated historic towns east of the Mississippi. Plenty of influential Revolutionary War characters spent time here. During the Civil War, the town experienced some of the bloodiest battles. Visitors should definitely make time to see these battle sites, which often feel more accessible than some of the bigger, more famous battlegrounds. Other sites that can’t be missed include the Mary Washington House, the Kenmore Plantation, and the Rising Sun Tavern, all of which belonged to relatives of George Washington; the James Monroe Museum and Memorial Library; and Chatham Manor, a former plantation and slave rebellion site turned Civil War hospital.

Galena, Illinois

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This small town in Illinois has historical significance in a range of topics. Despite being home to fewer than 4,000 people, Galena has repeatedly been called one of the best places for architecture in the entire country. That’s right, it makes the same lists as such architectural hotspots as Chicago and New York! These buildings come in varying styles from a number of different time periods, but nearly all have been carefully restored and repurposed. Fun fact: Galena was once home to a whopping nine Confederate generals.

Greenville, Pennsylvania

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Greenville, a small Pennsylvania town of about 6,400 people, might just have enough historical significance for a town ten times its size! Way back in August 1795, the Treaty of Greenville was signed by a group of local Americans and a coalition of Native American tribes. The treaty allowed settlers to populate western Pennsylvania without fear of Native American retaliation. Nearly a century and a half later, in 1942, the World War II Camp Reynolds saw about a million U.S. soldiers pass through on their way to Europe. Judy Garland even came to Greenville to entertain the troops. But the town’s historical significance doesn’t end there. Greenville is home to an extremely rare Smith Cross Truss-type covered bridge built in 1868, and is also the hometown of Stefan Banic, a Slovakian immigrant who designed the first working parachute.

Harpers Ferry, West Virginia

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While most out-of-towners find themselves in West Virginia for the national parks, we think Harpers Ferry is well worth the side trip — especially for history buffs and those hiking the Appalachian Trail. Harpers Ferry’s long history stems from the fact that it is the geographic meeting point of Virginia, West Virginia, and Maryland, and as such, it has quite the historic ambiance.Check out the town’s collection of old buildings, many of which have gone untouched for more than a century, while listening stories of local Civil War skirmishes over a pint or two of locally brewed beer.

Hartford, Connecticut

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Hartford, Connecticut’s long history includes a very important literary past. Visitors to Hartford can see the home and even step onto the porch where Mark Twain lived for many years and wrote his classic “Huckleberry Finn.” Next door to Twain’s home is that of Harriet Beecher Stowe, author of “Uncle Tom’s Cabin.” And of course, there is also an impressive collection of colonial-era sites, as well.

Hudson, New York

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Those who love historic architecture are sure to get a kick out of Hudson, New York. Houses, hotels, and businesses — Hudson is full of architectural styles that were popular from the 1700s through the 1900s. And despite intense renewal efforts in surrounding communities, Hudson’s buildings have remained protected. Specific architectural gems include the Hudson Opera House, Columbia County Courthouse, Hudson Area Association Library, and the First Presbyterian Church.

Lexington, Virginia

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Lexington, Virginia is perhaps most famous as the home of the prestigious Washington & Lee University, but this small town is also well known for its dedication to preserving its historic past. Downtown Lexington is lined with Victorian buildings turned into shops and restaurants, and has been so carefully preserved that the entire main street is listed on both the State and National Registers of Historic Places.

Mackinac Island, Michigan

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A visit to Michigan’s Mackinac Island is like stepping back in time to the golden Victorian age. Cars aren’t allowed on Mackinac, so horse-drawn carriages and bicycles tend to be the preferred forms of transportation. Speaking of bicycles, we suggest renting one to cycle around the island. Over the course of eight miles, cyclists will pass old fur traders’ forts, lots of lovely turn-of-the-century vacation homes, and pebbled beaches with stunning views of Lake Michigan. Mackinac’s downtown area is lined with charming old-fashioned stores selling everything from homemade fudge to antiques.

Marblehead, Massachusetts

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Marblehead may not make many guidebooks, but this charming small town, located about 17 miles from Boston, packs a big punch historically speaking. Marblehead’s “old town” is made up of crooked streets and the largest collection of pre-Revolutionary homes anywhere in the United States. Blink and you’ll miss a colonial fort, a powder house, various burial grounds, pirate alleys (!), and the country’s oldest Episcopal Church, built in 1714.

Murphy, North Carolina

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Murphy, North Carolina is one of the many sites you can visit along the Trail of Tears, the trail used by the U.S. Government to forcibly remove thousands of Cherokee Indians from their homelands. Visitors to Murphy can learn more about the Trail at the Cherokee County Historical Museum, where tons of interesting exhibits and Native American artifacts are on display. At nearby Fort Butler, visitors can read the names of the more than 3,000 Cherokee prisoners engraved on a commemorative wall.

Nags Head, North Carolina

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When in search for that perfect summer beach destination, drive right on past Hilton Head and travel to Nags Head, an 11-mile stretch of beach complete with secluded and relaxing beaches, wild ponies, and the tallest lighthouse in the United States. While we admit most of Nags Head’s appeal comes in the form of water and recreation, this tiny corner of the world has an interesting history as well. Its most famous site? That would be Roanoke Island, where The Lost Colony settlers arrived in America a whole 30 years before the pilgrims landed at Plymouth Rock.

Nantucket, Massachusetts

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While Nantucket can hardly be considered underrated in terms of appealing places and popular vacation spots, as an historical destination, Nantucket may come as a big surprise. This small island off the coast of Massachusetts was once one of the most important whaling centers in the U.S. Today, visitors can learn all about Nantucket’s important past at the Whaling Museum. Housed in a restored 1840s candle factory, the museum features a number of interesting artifacts, including a 46-foot skeleton of a sperm whale, and lots of information about the Essex, the ship that was destroyed by a sperm whale in 1820 and provided the inspiration for the novel Moby Dick. Of the Essex, only two items remain: a piece of twine and a sketch done by a survivor.

New Castle, Delaware

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Located just south of Wilmington, New Castle, Delaware is a blink-and-you-miss-it small town with tons of history. Though founded in 1651 as an outpost of the Dutch West India Company, New Castle was a Native American village long before that. Today, the town is full of cool historic features like cobblestone streets, a medieval-style town green, and stunning architecture like that of the Old New Castle Courthouse, which once served as the capitol for Delaware Colony.

Newport, Rhode Island

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Newport, Rhode Island may be best known as a cool summer beach destination, but it turns out this small town has quite a history, too. Newport was founded in 1639 by a splinter group of religious dissenters. It’s home to a number of unique historic sites, including: Touro Synagogue, the oldest synagogue in the U.S.; the Mystery Tower, which may or may not be a Norse settlement; and the Old Colony House, a fine Georgian-style government building that dates back to the 1740s.

Norris, Tennessee

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In the 1960s, Norris resident John Rice Irwin began his collection of random, everyday items that he thought were important and worth keeping. When his collection outgrew his garage, he built a cabin on his property to house all of his treasures. Today, Irwin’s modest collection takes up 63 acres, 35 historic structures, and even includes a restaurant and gift shop. It is associated with the Smithsonian Institution as the Museum of Appalachia, and its quarter-of-a-million artifacts (many of which include handwritten index cards to describe their history) has been called one of the best amateur preservation collections in the world.

Norwalk, Connecticut

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History is trendy in Norwalk! At least, the South Norwalk Historic District, or SoNo, is one of the most popular hangouts in town. Here, visitors and locals can visit top-notch restaurants, stores, and other sightseeing attractions housed in old buildings that have been carefully restored and repurposed. One such historical sightseeing attraction is the Lockwood-Mathews Mansion Museum, a second empire-style home built in the 1860s. Walking the nearby Sheffield Island Lighthouse and Nature Trail is a great way to learn about the surrounding area’s maritime history while also getting some exercise amongst beautiful scenery.

Oak Ridge, Tennessee

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After the attack on Pearl Harbor, a new city was created to produce the world’s first atomic weapons. This city, Oak Ridge, Tennessee, was built on 59,000 acres of rural farmland and had a population of 75,000 people in fewer than three years. Today, the eeriness remains in this “Manhattan Project” town meant to create bombs. Visitors can see some of the original buildings that housed the majority of the work, plus get an in-depth look at Oak Ridge history at the interesting museum and its exhibit “Oak Ridge: World War II’s Secret City.”

Portsmouth, New Hampshire

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Portsmouth, New Hampshire is the second oldest town in the state. Originally settled in 1623, Portsmouth is full of exciting historic architecture that reflects the various periods of Portsmouth’s past. Dating back to 1695 is the Strawbery Banke (sic), a 10-acre settlement and one of the oldest historic homes in town. Other impressive old houses and buildings include the Georgian-style Warner House (1716), the Moffatt-Ladd House (1716), the Wentworth-Gardner House (1760), and the John Paul Jones House. For history buffs, the nearby Portsmouth Naval Base is where the Russo-Japanese War was ended in 1905 with the Treaty of Portsmouth.

Saluda, North Carolina

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Most people who know where to find Saluda, North Carolina (for the record, it’s located “where the Foothills end and the Blue Ridge begins” about 30 miles from Asheville) come for the top-notch selection of outdoor recreation. Thanks to the Greenville Watershed and the Green River Game Lands — more than 18,000 acres of protected lands — hiking, mountain biking, fishing, and tubing down the river are all popular pastimes. The whole town is listed on the National Register of Historic Places and has a charming historical vibe for history buffs, with cozy old buildings, narrow streets, and lots of festivals to celebrate its past.

Thomasville, Georgia

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Despite being founded in 1825, it wasn’t until the arrival of the railroad nearly 40 years later that Thomasville was given a place on the map. Most of the town’s history has to do with the Civil War, during which it was a supply point for Confederate soldiers. Today, the town is full of interesting historic markers, plus dozens of grand Victorian mansions and big old plantation homes.

Williamsburg, Virginia

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There’s no place quite like Williamsburg, Virginia, a living museum where visitors can see first-hand what life was like when the town was still the capital of Virginia Colony. Many of the buildings and historical sites have been lovingly restored or left completely intact over the years, despite taking an especially rough beating during the Civil War. Wander through and learn such things as how meals were prepared (and enjoyed!), how horse shoes were made and placed on horses, and so much more.