Maryland has no shortage of charming small towns. These 10 in the Old Line State are also some of the best towns in Maryland for a weekend getaway. Filled with lovely accommodations, delicious restaurants, outdoor attractions, and more, these towns offer a local vacation that you’re sure to love. Check ’em out below, and start planning your next Maryland weekend getaways now!

1. St. Michaels
Saint Michaels, St Michaels, MD 21663, USA
John Ward / Getty Images
St. Michaels is known for its charming inns and bed and breakfasts. This area makes a lovely getaway for couples or families. Enjoy the seafood restaurants and prepare to shop 'til you drop at the numerous boutiques.
2. Havre de Grace
Havre de Grace, Havre De Grace, MD 21078, USA
Doug Kerr / Flickr
Havre de Grace has a downtown area that's full of interesting shops. You'll also want to take a stroll along the waterfront, as well as seek out Concord Point Lighthouse. Bring your camera!
3. Solomons
Solomons, MD, USA
Andrew Belair / Flickr
This little island town has sprawling water views galore. Chow down at the local eateries, hang out at the small beach, and be sure to seek out the one-of-a-kind local attractions. Calvert Marine Museum is a must when visiting the area.
4. Oakland
Oakland, MD 21550, USA
David Brossard / Flickr
Now we travel all the way west to Oakland, Maryland. This mountain town is full of historic charm and is absolutely stunning during autumn. In fact, the annual Autumn Glory Festival is a several-day event with all sorts of things to do. Don't forget to visit Swallow Falls State Park and Deep Creek Lake while you're here!
5. Chesapeake City
Chesapeake City, MD, USA
golfnride / Flickr
This charming Maryland town is nestled right next to the Chesapeake and Ohio Canal. That means that you can watch large ships pass through all day (and night). During the day you'll also want to shop, eat at the local restaurants, and just enjoy the peaceful, beautiful atmosphere.

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6. Ellicott City
Ellicott City, MD, USA
Joe Haupt / Flickr
This Maryland Main Street area is full of character, from the bold red bridge to the unique shops. When you're not shopping, you'll want to visit the local eateries, learn at the railroad museum, and take to the local trails. The Trolley Line #9 trail is a paved, easy trek that will lead to downtown Catonsville!
7. Thurmont
Thurmont, MD 21788, USA
Rain0975 / Flickr
This town of Thurmont, Maryland, is home to plenty of local businesses, but it's the surrounding outdoor attractions that will really wow you. Seek out the historic covered bridges and enjoy hikes galore at Catoctin Mountain Park and Cunningham Falls State Park. Natural beauty abounds!
8. Chestertown
Chestertown, MD 21620, USA
Michael Stokes / Flickr
Chestertown is located right along the Chester River. When you're not taking in the local water views, you'll want to head downtown to shop at all of the boutiques. The historic buildings and inns all around will transport you to the past in the best of ways.
9. Oxford
Oxford, MD 21654, USA
stephencearley / Flickr
This eastern shore town is home to Oxford Bellevue Ferry, which is the oldest privately-owned ferry in America. There's also a small beach here that's perfect for families, as well as historic bed and breakfasts that offer a charming stay. The water views can't be beat!
10. North Beach
North Beach, MD, USA
Mr.TinDC / Flickr
North Beach, Maryland, is sort of a 2-for-1 town, with the town of Chesapeake Beach being right next door. Hunt for fossils in the sand, eat and shop at the local businesses, and enjoy sunny days on the bay. This area is a popular spot for fishermen looking for a big catch.

Are there any other cute Maryland towns you’d add to the list of amazing weekend getaways? Where are your favorite spots around the Old Line State for a weekend getaway? Reach out and let us know! If you’re in search of even more Maryland charm, check out this list of even more peaceful small towns in Maryland.

 

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More to Explore

Maryland Weekend Getaways

Sarah M. | September 20, 2022

What are other cute towns in Maryland?

In terms of charming and cute towns, Maryland certainly has the market cornered! In addition to the charming towns for weekend getaways listed above, we guarantee you'll fall in love with other cute small towns in Maryland, such as:

  • Frostburg
  • McHenry
  • Cumberland
  • Hancock
  • Boonsboro
  • Walkersville

 

In fact, Walkersville takes the cute quotient to another level with the eponymous Walkersville Southern Railroad. This ride will take you along scenic routes that you won't soon forget. Here's more on this scenic train ride in Maryland that belongs on your bucket list!

What are the best small town Main Streets in Maryland?

Filled with restaurants, events, galleries, and much more, here are the Maryland towns that are home to some of the most lively Main Streets:

  • Ellicott City
  • Frederick
  • Berlin
  • Sykesville
  • Cumberland

 

So if you're looking for a charming town in Maryland to visit, clearly we’ve got plenty of those. One of our favorite Main Streets in Maryland to explore is St. Michaels. Along with a plethora of shops and eateries, St. Michaels also has a few charming bed & breakfasts if you want to stay for the weekend. The downtown area is perfect for a summer day trip, as St. Michaels, Maryland is hailed as one of the most walkable Main Streets in America!

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