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!
- St. Michaels
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. Saint Michaels, St Michaels, MD 21663, USA
- Havre de Grace
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! Havre de Grace, Havre De Grace, MD 21078, USA
- Solomons
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. Solomons, MD, USA
- Oakland
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! Oakland, MD 21550, USA
- Chesapeake City
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. Chesapeake City, MD, USA
- Ellicott City
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! Ellicott City, MD, USA
- Thurmont
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! Thurmont, MD 21788, USA
- Chestertown
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. Chestertown, MD 21620, USA
- Oxford
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! Oxford, MD 21654, USA
- North Beach
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. North Beach, MD, USA
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!
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.
Saint Michaels, St Michaels, MD 21663, 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!
Havre de Grace, Havre De Grace, MD 21078, 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.
Solomons, MD, 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!
Oakland, MD 21550, 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.
Chesapeake 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!
Ellicott City, MD, 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!
Thurmont, MD 21788, 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.
Chestertown, MD 21620, 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!
Oxford, MD 21654, 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.
North Beach, MD, USA
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The OIYS Visitor Center
Maryland weekend getaways September 20, 2022 Sarah M. 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!
The OIYS Visitor Center
Maryland weekend getaways
September 20, 2022
Sarah M.
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!
The OIYS Visitor Center
The OIYS Visitor Center
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!
