15 Historic Towns In Maryland That Will Transport You To The Past
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Jamie Alvarenga
Author
One of my favorite ways to spend a day is by exploring historic towns in Maryland. They offer so much in terms of uniqueness, charm, and history. Many offer antique shops and family-owned businesses filled with knick-knacks and handmade items. If you also love old towns in Maryland, then you’ll want to check out these spots!
Saint Michaels, St Michaels, MD 21663, USA
It’s hard not to become smitten with the town of St. Michaels, one of many old towns in Maryland. This nautical spot boasts historic buildings, restaurants, and more. During the holiday season, the town transforms into a Christmas wonderland that’s like stepping into the past. Learn more about what you can expect in a visit to St Michaels.
Berlin, MD 21811, USA
Many folks make Berlin’s historic area a traditional stop along the way to Ocean City. There’s even a general store with old-fashioned necessities that will fill you with nostalgia. There’s always something going on here, so we recommend visiting this historic town in Maryland's website for a list of all the fun upcoming events. Christmas happens to be a great time to visit Berlin.
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Chestertown, MD 21620, USA
With a motto of "Historic colonial town on the Chester River," it’s obvious that Chestertown is a historic Maryland town. This spot was founded in 1706 and still has a plethora of old buildings, many of which have been transformed into charming bed and breakfasts. Be sure to also check out the local ships for a glimpse into the past. Discover more about what you can do in a visit to Chestertown.
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Boonsboro, MD 21713, USA
Founded in 1792, one of the oldest towns in Maryland is filled to the brim with historic spots, including a Civil War museum. And be sure to also check out Washington Monument State Park. Civil War reenactments aren’t uncommon around the town and seeing the authentic costumes in person is fascinating. Learn more about what Boonsboro is all about.
Saint Marys City, St Marys City, MD, USA
Maryland’s first colonial settlement is the perfect spot for a day trip filled with knowledge. See what life was like centuries ago, from farming techniques to colonial games and festivals. Visiting this old town in Maryland during Maryland Day is a must! Learn more about St. Mary's City.
Havre de Grace, Havre De Grace, MD 21078, USA
This waterside town dates back to 1785, and today, you can find local shops and restaurants that fit right in with the historic towns in Maryland vibe. Be sure to visit Concord Point Lighthouse while you’re there, as it’s the perfect spot for a bit of Maryland scenery – and photos. Check out this list of things to do in Havre de Grace.
Frederick, MD, USA
Dating back to 1785, Frederick is one of the oldest towns in Maryland, but it also offers plenty of modern amenities. The food scene here is delectably good and the restaurants are housed in old buildings full of character. This spot is great for a day trip, especially during the holiday season. Get more reasons why Frederick is worth a visit.
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Ellicott City, MD, USA
Walking through historic Main Street, you wouldn’t know that Ellicott City is so close to larger cities. The town was founded in 1772, and today, the community strives to keep this area full of historic character. Between perusing the local boutiques, be sure to also check out the Ellicott City B & O Railroad Museum and the classic red railroad bridge that proudly displays the town name. And give yourself some time to take in the Ellicott City shopping.
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Dating back to 1684, Cambridge is one of the oldest colonial cities in the state. The downtown area has a few eateries and businesses located in buildings that beckon to the past. Or head toward the waterfront and witness Victorian bed and breakfasts that are so inviting, you may be enticed to stay the weekend in this historic Maryland town. Learn more about why Cambridge is a must-visit.
Oldtown, MD 21555, USA
This old colonial town is surrounded by natural scenery, adding even more beauty to the historic sites. A day full of outdoor exploring awaits as you visit the local landmarks and stroll along the C & O Canal that runs along this old town in Maryland. Learn more about the beauty of Oldtown.
Cumberland, MD 21502, USA
One of the most historic towns in Maryland, Cumberland was founded in 1787 and still retains plenty of vintage buildings that are all unique in their own way. While in the area, be sure to visit the Embassy Theatre for a taste of old Hollywood. A steam-engine train ride on the Western Maryland Scenic Railroad is also sure to infuse your day with some hands-on history. Get all the info on the Western Maryland Scenic Railroad.
Oakland, MD 21550, USA
Some might call Oakland a railroad town, as trains are always running along the tracks behind the station. Visit this spot for perfectly aged structures paired with a beautiful mountain backdrop. We highly recommend checking out the annual Autumn Glory Festival that takes place each fall. There is also plenty of antique stores in Oakland.
Annapolis, MD, USA
The history of Maryland’s capital is impressive in more ways than one. The Maryland State House is the oldest in continuous legislative use in the entire US. The Naval Academy is also an iconic site, training some of our nation’s best for over a century. The list of historic sites here goes on and on, and we recommend visiting this historic Maryland town for yourself to see them all. Here are some awesome Annapolis day trips.
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Sykesville, MD 21784, USA
Jamie Alvarenga / Only In Your State
Perusing Sykesville’s Main Street is the perfect way to spend a few hours on a weekend. Check out the pubs and shops that line the road, housed in beautiful structures from yesteryear. Learn more about the charm of Sykesville.
Chesapeake City, MD, USA
This tiny town on the C & D Canal boasts dozens of old homes that have been converted into charming shops and bed and breakfasts. Life moves at a slower pace here, keeping your visit peaceful and quiet. Get details on planning your trip to Chesapeake City.
What are your favorite historic Maryland towns? Tell us in the comments!
For more worthwhile destinations you can visit around the state, check out Maryland road trips.
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More to Explore
Maryland Towns
Are there any beach towns in Maryland?
If historic towns in Maryland aren’t your thing, know that there are many other towns with different types of attractions. There are 3,190 miles of coastline in the state, so there are quite a few beach towns in Maryland:
- Solomons: This spot in Calvert County is a popular area for water recreation along the 110-mile-long Patuxent River. Enjoy boating and harbor cruises, or head to the shops and seafood restaurants.
- North Beach: This small town is located on the Chesapeake Bay. It features a beautiful beach, plenty of shopping, and restaurants, spas, and nightlife.
- Ocean City: Located along 10 miles of the Atlantic Coast, this town is quite well known for its beach amenities. Enjoy swimming and other beach activities as well as a variety and dining and nightlife options.
What are the best Maryland towns for dining?
Attention all foodies! Here are some of the best Maryland towns for dining:
- Baltimore: This large city has over 3,500 restaurants to choose from. Just some of the best are the Venezuelan Alma Cocina Latina, the Indian Ananda, and the Northern Italian Cinghiale.
- Columbia: Located in Howard County, Columbia is also well known for its excellent dining. Some of the best restaurants include the American Cured, Mission BBQ, and the Turkish Cazbar.
What are the smallest towns in Maryland?
While Baltimore is the biggest city in Maryland at 80,94 square miles, there are quite a few places that are much smaller. Check out some of the smallest towns in Maryland:
- St. Mary’s City: A mere 1.2 square miles, this St. Mary's County town was founded in 1634. It’s a great spot for history buffs with public living history museums and a restored original colonial settlement.
- St. Michael’s: This Talbot County town is 1.3 square miles. Its most popular places include the Chesapeake Bay Maritime Museum and all the readily available water recreation throughout.
- Oakland: This former railroad town in Garrett County is 2.7 square miles and is great spot for nature lovers with the 257-acre Swallow Falls State Park. And there is also the B&O Museum.