10 Small Towns In Maryland That Are Full Of Charm And Perfect For A Weekend Escape

Maryland has no shortage of charming small towns. These 10 in the Old Line State are also great 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!

Are there any other 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? Let us know in the comments!

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Maryland weekend getaways

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, and 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?

If you're looking for a charming town in Maryland to visit, we’ve got plenty of those. Filled with restaurants, events, galleries, and much more, there are Maryland towns that are home to the most lively Main Streets. 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!