1. Hampstead, MD
Hampstead, which was established 1888 and has a little over 6,000 residents is located 30 miles northwest of Baltimore. This quaint small town is filled with Colonial homes, Civil War markers and friendly residents.
2. Monkton, MD
Monkton is a gorgeous town not far from Baltimore made up of sprawling countryside and old historic homes and horse farms. With a population of about 4,800 people, this quiet area is the perfect place for a peaceful getaway.
3. Chestertown, MD
Chestertown dates back to the 17th century and has a rich maritime history. Explore the replica of an 18th century ship the Schooner Sultana or take part in one of their many fun events. Every year the town throws the Chestertown Tea Party Festival, which reenacts the tea throwing of 1774.
4. Millwood, VA
Millwood is about 70 miles from Washington DC but it feels like a world away. Millwood is home to many of the area’s most historic buildins and sites that date back to the late 1700s.
5. Port Tobacco, MD
Port Tobacco has a population of 16 people. The history of Port Tobacco dates back to its Native American inhabitants and it has a fascinating history. Many of the homes date back to the 1700s and was once a bustling sea port. While much quieter now, it’s not far from La Plata so it’s close enough to plenty of bars, restaurants and hotels.
6. Floyd, VA
There’s one stoplight in Floyd, VA and around 400 residents. But on Friday nights at the Floyd County Store, the locals come together for an old fashioned Friday Night Jamboree where the bluegrass music plays loudly and you can’t help but tap your feet!
7. Waterford, VA
Just 47 miles north of DC, the entire village of Waterford is a National Historic District Landmark. It was founded in 1733 and today it is still a testament to its farming roots.
8. Staunton, VA
Tucked away in the Blue Ridge Mountains, Staunton features gorgeous Victorian architecture and plenty of culture. President Woodrow Wilson was born in Staunton and its now the home of the Woodrow Wilson Presidential Library, as well as, the American Shakespeare Center.
9. Harpers Ferry, WV
Surrounded by the Potomac and Shenandoah Rivers, Harpers Ferry is a 19th century village perfect for touring, hiking and biking. The Appalachian Trail cuts right through Harpers Ferry and visitors will love the unique shops and restaurants in the area.
10. Kilmarnock, VA
Kilmarnock is a charming town a little over 100 miles outside of Washington DC. It’s a hot spot for those who are hunting for antiques but it also offers plenty of shopping and dining options while staying true to it’s small town roots.
11. Doylestown, PA
Doylestown is an artsy Pennsylvania town where visitors can enjoy an array of museums, shops, boutique cafes and eateries. The Victorian architecture and gorgeous surroundings make it an amazing weekend getaway, just there hours away from DC.
12. Occoquan, VA
Occoquan has a wonderful warm and friendly atmosphere. Their downtown is walkable and is full of charming shops and a gorgeous waterfront. With around 1,000 residents, it’s a great place to achieve the small town, hometown feel while still being commuting distance to DC.
13. Warrenton, VA
The streets of Warrenton are lined with beautiful historic homes and it’s a city that is full of historic tradition. The downtown area is walkable and you can visit many historical buildings, as well, as boutique shops.
14. Easton, MD
Ranked as the “8th Best Small Town in America,” Easton is a quaint town in a picturesque setting. Stroll through tree lined streets, stop in at local shops and enjoy a delicious meal at one of their renowned restaurants.
15. Leonardtown, MD
Leonardtown has been described as a cross between Mayberry and Annapolis. Offering 300 years of history, you can begin your visit in the charming town square is one of the few original town squares in the state. From there you can explore the welcoming town and its many restaurants, galleries and shops!
16. Ellicott City, MD
The train station in Ellicott City is the original that was part of the first 13 miles of railroad in the country. Today, Ellicott City is home to picturesque homes, unique shops and restaurants and many historic buildings and sites.