Use Your PTO for These Irresistible Road Trips in Maryland

Whether you have a day or a week, there are plenty of places to go in our state when you have time off work. Maryland has nautical destinations, fresh farm getaways, lakeside vacations, and tasty tours. Here are four irresistible road trips in Maryland to plan your PTO around. 

Nautical Charm in Annapolis 

Maryland’s capital, Annapolis, is one of America’s prettiest and most walkable cities. It is known as a nautical destination due to its location on the Chesapeake Bay and its reputation as the “Sailing Capital of the World.”

The historic downtown area offers a great introduction to the city and provides plenty of places to eat, stay, and play on the waterfront. 

Stay

• Annapolis Waterfront Hotel is an award-winning hotel with nautical-themed rooms and stunning views of the Chesapeake Bay. Guests who arrive by water can park their boats at the hotel’s dock for an overnight stay or dinner at Pusser’s Caribbean Grille.
• 134 Prince is a luxury boutique hotel with gorgeous suites, sophisticated décor, and relaxing gardens.

Eat

• Chick & Ruth’s is a famous Annapolis deli with “colossal” food challenges, famous crab cakes, and an in-house bakery. 

• Choptank is a waterfront fish and crab house specializing in Maryland cuisine, including local seafood, steamed blue crabs, and house-battered Eastern Shore fried chicken. Grab a seat on the deck or rooftop to enjoy the view while eating.

Do

• Annapolis Sailing Cruises offers private and public cruises on 74-foot wooden schooners. Public cruises set sail from the Annapolis Waterfront dock four times per day.
• The United States Naval Academy (USNA) is an undergraduate college that trains officers for the U.S. Navy and Marine Corps. Visitors can tour the world-famous academy and learn about its history from a certified guide.

Mark Your Calendar

• Fall boat shows, including the Annapolis Powerboat Show and Annapolis Sailboat Show, come to Annapolis City Dock in October each year. 

Bikes & Brews in Frederick

Downtown Frederick is known for bikes and brews (among other things). It has a walkable downtown brewing district and is home to the only high-wheel race in the United States.

The downtown area also contains over 200 shops, restaurants, galleries, and performing arts venues.

Stay

• 10 Clarke Place is an architecturally significant Queen Anne Victorian bed and breakfast featured on HGTV’s Restore America. Guests get a three-course gourmet breakfast, evening refreshments, and bike storage, maintenance, and route recommendations.
• Hollerstown Hill Bed and Breakfast is a boutique Victorian bed and breakfast. Guests get a full country breakfast in the morning and have access to bicycle storage and rentals. 

Drink

• Gravel and Grind is an artisanal coffee shop that rents, sells, and repairs bicycles. They also have yummy toast.

• Frederick’s craft breweries and distilleries are the place to sip and sample locally-produced beers, cider, wine, and spirits.
• Non-alcoholic drinks can be found at the Pop Shop, a downtown soda shop with 400+ varieties of glass bottle soda pops.

Do

• The Covered Bridge Bicycle Route is a picturesque tour of Frederick County and three historic covered bridges. The 40-mile route was named the best bike ride in Maryland by Bicycling.com.

• The Frederick History Bicycle Loop is a 10-mile ride through Frederick’s 50-block historic district with stops at museums, local Civil War sites, a Francis Scott Key Monument, and other unique spots.

Mark Your Calendar

• The Maryland Craft Beer Festival is in May at Carroll Creek Linear Park in downtown Frederick.
• The National Clustered Spires High Wheel Race is held in July in downtown Frederick.

Outdoor Fun at Deep Creek Lake

Deep Creek Lake is a fun and scenic destination in the mountains of Western Maryland. The area is known for providing outdoor recreation and adventures in all four seasons. If you love taking road trips in Maryland, you might already be familiar with Deep Creek!

Stay

• Wisp Resort is a 4-season ski, golf, and recreational destination resort on the edges of Deep Creek Lake. They have lots of rooms to stay in, several restaurants and cafes, and a full-service ski shop.

• Meadow Mountain Campground is a 100+ site campground in Deep Creek Lake State Park with basic sites, electric sites, mini cabins, a yurt, and a three-sided Adirondack-style shelter called the Bear Den.

Eat

• Ace’s Run Restaurant & Pub is a farm-to-table restaurant that serves comfort food with a twist. It has a changing seasonal menu, balcony dining, boat docks, and lake views.
• Brenda’s is a New York-style pizzeria specializing in scratch-made pies.

Do

• Deep Creek Lake State Park is a 1,800-acre park with the largest lake in Maryland. It is a fun place for watersports, including boating, kayaking, jet skiing, water skiing, tubing, and wakeboarding. You can also hike, mountain bike, or snowshoe on the park’s many trails.

• Thayerville Fire Tower offers an unforgettable bird’s eye view of the lake. The Meadow Mountain Trail at Deep Creek Lake State Park will take you to the tower.

Mark Your Calendar

• The Art, Wine & Spirits Festival is held annually in September
• The Autumn Glory Festival is held every October

Taste the Chesapeake in Cambridge

Dorchester County is known for local crabs and oysters. It also has lots of farms with fresh produce and rolling countryside. One of the most incredible places to visit is Cambridge, an old colonial city on the banks of the Choptank River. It is beautiful, friendly, and very walkable. 

Stay

• Hyatt Regency Chesapeake Bay Resort is a 350-acre resort on the Cambridge waterfront. Amenities include a marina, spa, golf course, and nature trail.

• Cambridge House Bed & Breakfast is an 1847 sea captain’s manor on Cambridge’s historic High Street converted into a seasonal bed and breakfast.

Eat

• Dive Club is a family-friendly themed restaurant that combines dinner and a show with visual effects and a story about Captain Bernard’s ship. Highlights include small plate tapas, tropical cocktails, and a raw bar. 

• Old Salty’s Restaurant is a waterfront restaurant on Hoopers Island (about 40 minutes from Cambridge) known for fresh seafood. The drive to this destination restaurant goes through Maryland marsh and authentic watermen’s villages. 

Do

• Long Wharf is a park on the Choptank River waterfront. It is a great place to take a walk and see the Choptank River Lighthouse and Skipjack Nathan of Dorchester, an oyster-dredging wooden sailboat with public sails every Saturday in May through November.

• Emily’s Produce is a seasonal farm market with a full-service kitchen, children’s play area, and u-pick strawberries, blueberries, blackberries, pumpkins, and wildflowers.

Mark Your Calendar

• Powerboat races, including the Cambridge Classic Powerboat Regatta in May and the Thunder on the Choptank in July. 
• The Choptank Heritage Skipjack Race is held on the fourth Saturday of September. 

 

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Skipjack Race in Cambridge, MD. Photo Credit: Jill Jasuta