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Small Town Getaways in Maryland

Each region in Maryland has darling small towns to make the perfect getaway. 

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C & O Canal Lockhouse 22
@follownicksadventures-Instagram

Forget what you’re getting away from, let’s focus on what you might be getting to, with amazing small town experiences across all of Maryland. Close your eyes (after you read this, of course) and imagine checking in to a friendly B&B, dining like you’re family at main street cafes and meandering through local attractions. Here are suggestions for a few days of small town getaways in each of Maryland’s five regions.

Frederick (Capital Region)

Whether you’re more likely to spend your weekend on a hiking trail or a wine trail, Frederick is a perfect home base. Book a few nights at 10 Clarke, a Victorian-yet-modern B&B that puts you in walking distance to 50 blocks of shops and restaurants in downtown. Foodies will be in heaven at  Dutch’s Daughter and Flying Dog Brewery. Sip your way along the Frederick Wine Trail that connects eight Maryland wineries while weaving through Civil War battlefields. The Catoctin Wildlife Preserve & Zoo is another must-see attraction in Frederick with more than 500 animals that you can ogle on a guided safari-style ride.

McHenry (Western Maryland)

Find an outdoor adventurer’s paradise in McHenry, on the northern shore of Deep Creek Lake. Places to stay in McHenry range from Blue Moon Rising—an eco-friendly tiny-home village—to the newly renovated, resort-style Lodge at Wisp. Rafting, kayaking, boating, hiking, zip-lining, tubing, rock climbing, golfing, go-karting, mountain biking, birding...and the list goes on for things to do in Western Maryland. In between all those activities, the food and beer scene will satisfy your appetite. Don’t miss the local suds and wood-fired pizza at Mountain State Brewing Company. If no day is complete without something sweet, Lakeside Creamery is the place for handmade ice cream in a fresh waffle cone.

St. Michaels (Eastern Shore)

Step into a postcard setting in St. Michaels, an historic harbor village on the shore of the Chesapeake. Picture champagne cruises at sunset, shops and cafes along quaint, brick-lined streets and the immersive Chesapeake Bay Maritime Museum. Book luxurious lodging at The Inn at Perry Cabin  and take advantage of the spa and golf course. Fill up on the freshest seafood, whether you’re craving to pick crabs by hand on the deck at The Crab Claw Restaurant, or dress up for a romantic white tablecloth experience at Stars Restaurant.

Solomons Island (Southern Maryland)

You can’t get any closer to the Chesapeake Bay than Solomons Island. Wake up to waterfront views and a three-course breakfast at Solomons Victorian Inn. The walkable location is ideal for morning recreation: walking, jogging, biking or sailing—depending on your desired speed. The wooded walking path through Annmarie Sculpture Garden features pieces on loan from the Smithsonian as well as a children’s natural play space. For lunch, try The Lighthouse, a landmark that overlooks Back Creek. Don’t forget to pop in to say hello to the otters at the Calvert Marine Museum and, when you’re in the mood for the freshest local seafood dinner, check out Stoney’s Kingfishers. Stoney’s is famous for its crab cakes—a Maryland classic.

Ellicott City (Central Maryland)

You may be familiar with the bigger, bustling cities in Central Maryland, like Baltimore or Annapolis, but you don’t have to look far to find a small-town feeling. Drop your anchor in Ellicott City for a few days to enjoy diverse places to stay, unique shopping and historic sites. Indulge in the amenities at Turf Valley Resort, including two golf courses, on-site spa and pool. Or, check in to the Wayside Inn B&B where it’s rumored that General George Washington once slept. If retail therapy is your kind of relaxation, don’t miss Old Ellicott City where boutiques have everything from home furnishings to the latest fashion, plus art galleries, bars and restaurants. Continue the shopping spree at Historic Savage Mill, an historic cotton mill that’s transformed into an eclectic collection of shops, galleries and restaurants. History buffs have plenty to see around Ellicott City, including Patapsco Female Institute Historic Park and the B&O Railroad Museum.

Charming small town getaways are waiting for you all around the state of Maryland. Whether you’re looking for an escape by the water, a place to indulge in retail therapy, or just a quiet location to relax and take in some beautiful scenery—small towns in Maryland have got you covered!

Downtown Frederick's retail area
Visit Frederick
Downtown Frederick
Scenic view of Deep Creek Lake in fall
Scenic view of Deep Creek Lake in fall
Enjoy the hands-on exhibits and overnight programs at the lighthouse at this museum.
Chesapeake Bay Maritime Museum (CBMM) in St. Michaels
Enjoy breathtaking sunsets at Solomons Island. Photo by Southern Maryland Photography
Southern Maryland Photography
Bridge to Solomons Island at sunset
ice cream shop
Park Ridge Creamery in Ellicott City