Hidden Gems: Small Towns With Deep Roots
These under-the-radar towns are full of history and charm
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Answer to last week’s quiz:
How many men under the age of 18 served in the Civil War?
Congratulations to those who guessed 251,000 to 400,00! It seems incredible, but there were an estimated 250,000 to 420,000 soldiers who were under the age of 18. AND at least 100,000 were under the age of 15!
Hello history-loving friends!
It’s summer and that means it’s road trip season! Today’s post is about small towns (that you may have never heard of ) that played a vital role in American history.
A lot of these towns are close to large historic touristy towns, so you can visit both. (But to me, exploring a small town is more interesting — and more relaxing).
If you enjoy brick-lined sidewalks, off-the-beaten-path battlefields, and one-of-a-kind museums, keep reading about these small towns with deep roots.
Note: Since 2026 marks the 250th anniversary of the Declaration of Independence, I only chose small towns for this list that have a strong connection to the Revolutionary War. I have lots of other historic small towns to share in the future that are historic for other reasons.
Without further ado, here are some intriguing small towns that should inspire you to take a Revolutionary Road Trip!
1. Georgetown, South Carolina
Population: 8,400
Georgetown, SC is often overshadowed by nearby Charleston, but it is a true American history treasure. Founded in 1729, this coastal town played a crucial role in the American Revolution.
Even if you’re not a history buff, you will be blown away by the historical homes, picturesque streets lined with Spanish-moss draped trees, and the beautiful waterfront walking area.
Places to visit: The Kaminski House Museum (you can take a virtual tour), and Georgetown County Museum, that spans almost 300 years of American life.
Pro Tip: The shopping is great too!
(Sixty miles to Charleston)
2. Paoli, Pennsylvania
Population: 6,000
Paoli, PA, is home to one of the lesser-known yet significant battles of the Revolutionary War. The Battle of Paoli, also known as the "Paoli Massacre," took place there in 1777.
Visit the Paoli Battlefield Historical Park to learn about this pivotal moment in American history. The town itself offers charming, historic architecture and a quaint, small-town atmosphere.
(Five miles from Valley Forge and 25 miles from Philadelphia)
3. Middleburg, Virginia
Population: 673
Middleburg, VA, is one of my favorite towns and it’s steeped in history. Mostly known for horses, wine and its role in the Civil War, this charming small town has deep historical roots.
Established in 1787, Middleburg will also please “foodies” and shoppers. You can spend a night or dine at the historic Red Fox Inn or the beautiful Welbourne Inn, which has been in the same family for generations.
The drive to this historic town is spectacular with well preserved scenic landscapes and historic charm.
Pro Tip: If driving from the east, you’ll pass Aldie and its famous mill that is open for tours.
4. Chester, Vermont
Population: 3,005
Chester, VT, may be small, but it’s big on history. Known for its historic Stone Village and charming colonial architecture, Chester offers a glimpse into 18th-century America.
The town’s picturesque setting and well-preserved buildings provide a perfect backdrop for exploring the nation’s early years.
5. Concord, Massachusetts
Population: 19,340
Even though this town is bigger than most of the other towns on my list, I had to include Concord, because of its historical significance.
Usually overshadowed by Boston’s Revolutionary War history, this town was the site of the famous Battle of Concord, one of the first battles of the Revolutionary War.
You can visit the Old North Bridge, where the "shot heard 'round the world" was fired, and explore the Concord Museum for a comprehensive look at the town’s rich history.
About 26 miles from Boston
6. West Point, New York
Population: 7. 340
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West Point is the oldest continuously occupied military post in the United States and is home to the United States Military Academy. Located on the Hudson River in New York, General George Washington stationed his headquarters in West Point in the summer and fall of 1779 during the American Revolutionary War, and later called it "the most important Post in America."
I highly recommend a tour of the historic West Point campus and a visit to the West Point Museum to delve into the military strategies and key figures of the era. The town itself offers stunning views of the Hudson River and a profound sense of American heritage.
Places to stay: The Thayer Hotel is adjacent to the West Point campus and has great dining opportunities.
7. Edenton, North Carolina
Population: 4,397
I did a book signing in Edenton, NC, many years ago and didn’t have time to explore as much as I would have liked.
Established in 1722, Edenton was a hotbed of revolutionary activity, including a group of women who had their own “tea party” and affixed their signatures to a document as a testament to their resolve and pursuit of independence.
You can take a guided tour of the Historic Edenton State Historic Site, which includes the 1767 Chowan County Courthouse and other significant buildings. The town’s waterfront location and historic charm make it a delightful destination.
8. Washington, Georgia
Population: 3,750
Washington, GA, boasts a rich Revolutionary War history and is often called the “Revolutionary Capital of Georgia.” The town is home to the Mary Willis Library, the oldest public library in the state, and the Washington-Wilkes Historical Museum.
Washington is close to the Kettle Creek Battlefield site, which is on my bucket list for 2025. You can also explore the town’s historic homes and churches, many of which date back to the 18th century.
9. Yorktown, Virginia
Population: 195
Everyone’s heard of Williamsburg, but nearby Yorktown, VA, is a name synonymous with American victory in the Revolutionary War.
The Siege of Yorktown in 1781 marked the end of the war and the beginning of the nation’s independence. Visitors can explore the Yorktown Battlefield, part of the Colonial National Historical Park, and the American Revolution Museum at Yorktown.
Distance to Williamsburg: 13 miles
Conclusion
These historic small towns offer more than just picturesque scenery; they provide a deep connection to America’s past.
I think you will also find they are all wonderful places to visit while offering an opportunity to experience the rich tapestry of America’s heritage.
Let me know if you’ve visited any of these — or if you have any other recommendations. I’d love to hear them!
Answer in next week’s post!