Ocean City, Maryland boardwalk. Image credit Yeilyn Channell via Shutterstock

10 Most Underrated Towns In Maryland To Take A Trip To

Just off the coast of the Atlantic Ocean, you will find the beautiful state of Maryland wrapped around the Chesapeake Bay. Many things make Maryland special, most notably the seafood you can find around the coast. You can also find tons of historical places and landmarks, thanks to the fact Maryland was one of the first states to be settled. While the big cities might seem more glamorous, there are plenty of other places to visit. 

Tilghman Island

The Lee House, Tilghman Watermen's Museum, Tilghman Island, Maryland, USA. By Acroterion
The Lee House, Tilghman Watermen's Museum, Tilghman Island, Maryland, USA. By Acroterion

Tilghman Island is a beautiful island town deep inside the Chesapeake Bay. One of the best ways to explore this water around here is by renting a boat from the Tilghman Island Marina. If you're with your family or friends, you can also rent jet skis and waterskis to make the day even more memorable. The Rebecca T. Ruark Charter provides tours and guides throughout the bay. The Wylder Hotel Tilgham Island backs right up to the beach, where couples can continue their romantic getaway.

Takoma Park

The intersection of Laurel and Carroll Avenues, By Farragutful
The intersection of Laurel and Carroll Avenues, By Farragutful

If you want to be closer to Washington, D.C., then Takoma Park is where you should look. Make sure you stay around the area, as there are tons of fun things to do when you're there. The Takoma Park Farmers Market is where locals bring in the freshest produce they have. You'll want to check them out every Sunday from 10 am-2 pm. Make sure you take these foods to Belle Ziegler Park. This park has plenty of benches to sit at and tons of areas to walk around after you're done eating. You can stay in Takoma Park for only around $100 per night, making it a great weekend trip. 

Chesapeake City

Chesapeake City along the Chesapeake and Delaware Canal, via Jennifer Schmidt
Chesapeake City along the Chesapeake and Delaware Canal, via Jennifer Schmidt

Right next to the Delaware border is Chesapeake City. Here, you'll find a beautiful winery called Chateau Bu-De. This winery offers excellent homemade wine tastings and a tour that you'll have to see to believe. The Bohemia River is right next to Chesapeake City and is a great area to walk around. You'll be able to clear your head on the path next to the river when you hear the water rushing. If you're with a group of friends who like extreme sports, make sure to check out the Outdoor Xtreme Chesapeake City Paintball Park. Playing paintball indoors is fun, but having the natural elements around you brings it to a whole new level.

Cumberland

Cumberland Maryland, Church, City, town.
Cumberland, Maryland, Church, City, town.

You can't get much farther north in Maryland than Cumberland. This town is right next to Tussey Mountain. Thanks to this, one of the most talked about things to do is explore the Great Allegheny Passage. This trail lets you experience what life was like in cities like Pittsburgh before the population exploded. Rocky Gap State Park is another great place to walk around and become one with nature. If you enjoy fishing, make sure you check out Lake Habeeb, one of the beautiful lakes inside this state park. The Charis Wine & Distillery has some of the most fantastic homemade wines and liquors around. This is thanks to the fresh fruit and ingredients that are grown around. You'll be able to taste-test these drinks and see what the locals can't stop talking about. 

Annapolis

Downtown Annapolis in Maryland
Downtown Annapolis in Maryland

Anyone with an appreciation for the military will love Annapolis. This is where the United States Naval Academy is. This campus is always complimented as being one of the most beautiful you'll see. History buffs will love to visit the Annapolis Historic District. This town was first settled in back in 1649, making it one of the oldest in the United States. You can see and experience what life was like back then for those who lived here. Anyone who wants to go to Maryland to be close to the water is in luck. Quiet Waters Park is a hiking trail that leads you right up to the water. Annapolis has a little bit of something for everybody. 

Ocean City

People at Ocean City Boardwalk in Ocean City , Maryland
People at Ocean City Boardwalk in Ocean City , Maryland

During those hot summer days, especially in the Maryland area, the best way to cool off is by going to the ocean. There aren't any better ocean towns to visit than Ocean City. The Ocean City beach is constantly discussed as one of the best beaches in the United States. There's tons of room for people to lay out in their towels and under their umbrellas all day. When you're ready for food and shopping, the Ocean City Boardwalk is where your next stop should be. You can get treats like funnel cakes and purchase new sunglasses if you need them while you're here. If you find yourself here during a time when the beach sounds dreadful, the Seacrets Distilling Company is a great place to go hang out. Even though it's new, it was made to look like it's from the Prohibition Era. There are plenty of tasting sessions throughout the year and something for everyone to drink. 

St. Michaels

St. Michaels, Maryland. USA. Street scape view of shops and restaurants
St. Michaels, Maryland. Street scape view of shops and restaurants

If you're fascinated by history and how people survived hundreds of years ago, then you should visit St. Michaels. The 1879 Hooper Strait Lighthouse is now a museum where you can learn about and see how ships used to make their way to Maryland. This was one of the most important things for coastal towns. Ships needed to know where to go and how far they could come before crashing. The Chesapeake Bay Maritime Museum goes into the history of ships in the bay and what daily life here has evolved from. Those looking to have a relaxing trip need to make sure they visit the Spa at Harbour Inn. You'll be able to book massages, be in a pool, and do whatever you need to become your best self. 

Boonsboro

Aerial view of Boonsboro, Maryland.
Aerial view of Boonsboro, Maryland.

Taking tours around national parks is a normal thing to do. Taking a tour through a crystal cave is one of the rarer things you'll get to do in life. In Boonsboro, you'll be able to do that. The Crystal Grottoes Caverns have some of the freshest and most natural crystals growing from the ceilings that haven't been plucked. The tour guides who take you here know their stuff and are excited to share the information with you. Hiking to the top of Annapolis Rock provides both amazing exercise and a glorious view you won't find anywhere else. The homemade burgers and french fries at Dan's Restaurant & Tap House will have your mouth salivating just thinking about the next time you go back. 

Oxford

Harbor of Oxford, Maryland.
Harbor of Oxford, Maryland.

What's more romantic than taking a ferry with your partner on the water during a sunset in Maryland? There's not a lot, and you can do this at the Oxford-Bellevue Ferry in Oxford. This tour will take you into the Chesapeake Bay for a memory that will last a lifetime. If you like fishing, the Oxford Charters have an expedition that takes you into the bay, searching for the biggest fish you can find. You must do these during the summer months, as this is when the weather will be the best. The Treasure Chest offers local arts and crafts like paintings for sale. The locals love to draw what they see every day since they know how amazing it is. 

Thurmont

Loys Station Covered Bridge in Thurmont, Maryland.
Loys Station Covered Bridge in Thurmont, Maryland.

You are not alone if you need a weekend away from it all, enjoying as many different beverages as you can. The Westminster Region Wine Tour is the perfect way to start it off in Thurmont. Here, you'll be able to tour different local wineries and try their homemade products. Cunningham Falls State Park has different trails that lead to Hunting Creek Lake. This lake has a great beach where anyone can unwind and not be among so many other people. If you go during the springtime, the Catoctin Mountain Orchard has different lilacs and flowers that are in full bloom. You can see the beauty of Maryland in person here.

The Takeaway

Maryland is known for having some of the most beautiful towns in the United States. Each one has its charm and something that makes it special. Thanks to where Maryland is on the map, you can find beach towns and places in the middle of nowhere right next to you. These towns stand out amongst the rest in Maryland, making them all a must-visit. 

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