Posted in Maryland Attractions, Road Trips, Small Towns July 25, 2021 by

Take This Road Trip Through Maryland’s Picturesque Waterside Towns For A Charming Experience

We’ve created quite a few Maryland road trips thus far, and today we’re bringing you one of the most picturesque. If you swoon over water views (who doesn’t?) then you’ll want to check out the following 10 towns. Take a few days to complete this entire trip and you’ll realize why it’s one of the most scenic Maryland road trips.

Click here to follow along with the Google Map. Ready? Let’s go!

You're sure to see the best of Maryland on this scenic coastal road trip!
Google Maps
1. Solomons
Flickr / Harold Neal
This island town is completely surrounded by water views. Stop by to enjoy some seafood and learn about underwater life at Calvert Marine Museum. The bridge to get onto the Island is part of the adventure - but you might not want to look down!

Find more information about this island town right here
2. North Beach
Flickr / jantos
This little town has a delightful boardwalk with sprawling views of the water and some of the best ice cream in the state! You can walk the rail trail or pick up a great crab dinner - this town is truly a choose-your-own-adventure. Be sure to also visit the nearby Chesapeake Beach for even more attractions, including charming antique shops.

Learn more about these beach towns right here.
3. Annapolis
Flickr / m01229
Maryland's capital is a great place to spend a day. Visit the local shops and eat at one (or several) of the unique restaurants. Stop by the Iron Rooster near Ego Alley to watch the sailboats turn and snack on homemade pop tarts!

See why we love Annapolis here
4. Havre de Grace
Flickr / Chesapeake Bay Program
This little town is actually known as the decoy capital of the world. Visit the quirky decoy museum followed by a bite to eat, and burn off those calories with a walk along the promenade. We know you've driven through it a million times - why not stop and visit?

What a charming place for a day trip!
5. Chesapeake City
Flickr / Chesapeake Bay Program
It's easy to fall in love with Chesapeake City for its calming water views and homey local businesses. Whether you explore by foot or boat, you're sure to have a wonderful time.

Find more information here.
6. Chestertown
Flickr / Kevin Thomas
While the downtown area offers historic views full of shops, the waterfront is perfect for spending a sunny day. It's like taking a step back in time, and you'll find yourself truly stopping to smell the roses.

Learn more about this delightful small town right here.
7. Rock Hall
Jamie Alvarenga / Only In Your State
This quiet fishing town offers scrumptious spots for seafood and has a few bed & breakfasts that are sure to relax you. It's a great spot for a vacation, if you feel like ending your road trip now!

Find more information about Rock Hall and all it has to offer right here.
8. St. Michaels
Flickr / Andy Melton
St. Michaels is a state favorite for its laid back atmosphere. Be sure to also check out the many town events throughout the year.

This town is our favorite hidden gem!
9. Ocean City
Flickr / Lee Cannon
The ocean beckons when you head to Maryland's most popular beach. With the relaxing breeze and hundreds of restaurant options, you may never want to leave. There's a reason this spot is so popular!

See what's happening in OCMD right here/
10. Crisfield
Flickr / kennykunie
Experience simpler times with a trip to Crisfield. You'll want to try the seafood while you're in town, and be sure to make a stop at Smith Island Baking Company for a slice of iconic Smith Island Cake.

Find more about Crisfield right here.

 

While there are even more waterside towns in Maryland, these are among the most charming. You may also be interested in this one vacation every Marylander should take at least once.

OnlyInYourState may earn compensation through affiliate links in this article.

Address: Solomons, MD, USA
Address: North Beach, MD, USA
Address: Annapolis, MD, USA
Address: Chesapeake City, MD, USA
Address: Crisfield, MD 21817, USA
Address: Ocean City, MD, USA
Address: Saint Michaels, St Michaels, MD 21663, USA
Address: Rock Hall, MD 21661, USA
Address: Chestertown, MD 21620, USA
Address: Havre de Grace, Havre De Grace, MD 21078, USA
The OIYS Visitor Center

Scenic Road Trips In Maryland

July 29, 2021
Kim Magaraci

What are the most charming towns in Maryland?
Maryland is packed with charming towns! Whether you're looking for tiny towns like Solomons or larger historic communities like Ellicott City, you're sure to find a place that captures your heart. Head to Berlin to get a taste for quiet coastal life, or visit Crisfield to enjoy world-famous cakes in a quaint setting. Out in Western Maryland, Oakland is the best place to enjoy fall foliage in the mountains.

Where can nature lovers go for great day trips in Maryland?
If you love nature, you'll want to head west! Western Maryland's mountains are famous for their rolling and rocky trails and gorgeous natural formations. Towns like Cumberland and Walkersville will introduce you to a side of Maryland life that most visitors and locals tend to skip right over. Some of the best hikes in Maryland can be found in Patapsco Valley Park, South Mountain State Park, Swallow Falls State Park, and the Chesapeake and Ohio Canal National Historical Park.