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Use Your PTO for These Irresistible Road Trips in Maryland

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.”

Aerial of Annapolis
Photo Credit: Visuals by Marcus

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

  • 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.
  • Chick & Ruth’s is a famous Annapolis deli with “colossal” food challenges, famous crab cakes, and an in-house bakery. 
Photo Credit: The Choptank
  • 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.
  • 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
Sunset over harbor in Annapolis with a ton of boats docked
Photo Credit: Annapolis Boat Shows
  • 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.

National Clustered Spires High Wheel Race
Photo Credit: André Chung

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

  • 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. 
  • Gravel and Grind is an artisanal coffee shop that rents, sells, and repairs bicycles. They also have yummy toast.
Gravel and Grind in Frederick, MD. Photo Credit: Gravel and Grind
  • 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.
Burger, fries, and beer at a brewery
Fifty Fifty burgers at Olde Mother Brewing. Photo Credit: Glenn VanLandingham
Roddy Road Covered Bridge
Roddy Road Covered Bridge. Photo Credit: C. Kurt Holter
  • 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

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!

Family having fun on Deep Creek Lake with a boat
Photo Credit: Deep Creek Lake & Garrett County, Maryland
  • 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.
Wisp Resort in the snow
Wisp Resort in Maryland. Photo Credit: Jessica Fike Photography
  • 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.
  • 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.
  • 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.
Deep Creek Lake State Park in Maryland. Photo Credit: Jess Daddio/ Maryland Department of Natural Resource
  • 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.
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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. 

Hyatt Chesapeake in MD. Photo Credit: Hyatt Chesapeake
  • 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. 
Dive Club in Cambridge, MD. Photo Credit: Jill Jasuta
  • 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. 
  • 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.
The Choptank River Lighthouse in Cambridge, MD. Photo Credit: Jill Jasuta
  • 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.
Road Trips in Maryland
Emily’s Produce in Cambridge, MD. Photo Credit: Jill Jasuta
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. 


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

About the Author

Anna Champagne is an outdoor writer, photographer, and traveler. She can often be found gardening and birdwatching in her backyard and exploring creeks, trails, marshes, and parks with her husband. Anna lives in Frederick County, Maryland. You can learn more about her on her website

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