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Maryland Small Towns


Sykesville:. This little town is an easy get away from Baltimore at a 40 minute drive and Washington D.C. at just over an hour. Voted the coolest small town in America 2016 by Budget Travel, Sykesville is a great place to stroll Main Street. This town's Main Street is a classic with boutique stores to get syke'd about. The 1.58 square mile town also packs in plenty of choices for dining, including sushi, grilled cheese or E.W. Beck's Pub on Main Street with all kinds of small town comfort food. There are many festivals, such as the newish Annual Ice Festival in February or the Art & Wine Festival in early May. Warmer weather brings a great farmer's market to town every Sunday and there are some interesting historical spots, including a restored one room schoolhouse that was for black children and a few nods at the railroad that was an important building block of this town. There are train cars filled with model trains, as well as old depots transformed into the town's post office and Baldwin's Station restaurant. The outdoors is not lacking either with free movies and concerts in the park during the summer months and fishing and floating on the Patapsco River. Sykesville is a perfect place to enjoy a slow paced Saturday or Sunday.

Chestertown: Small town charm is alive and well in Maryland and if you head over the river and past the bay there is another town to satisfy your travel "bug". Sykesville celebrates its railroad history, while Chestertown celebrates its maritime history with sailing ships still arriving in the port on the Chester River. The Schooner Sultana is an exact replica of a British Navy, 18th century ship that offers education programs but also becomes part of The Chestertown Tea Party Festival every Memorial Day when this towns tea party revolt is reenacted with "tea and British Soldiers" being thrown overboard. The festival also includes a grand parade, craft fair, old homes tours, a cocktail party and food vendors. Chestertown's historic district includes restored 18th century homes, beautiful churches, many art galleries, the county courthouse and, of course, shops and restaurants. High Street and Cross Street are the main streets of this town and with brick sidewalks, classic architectural details and summer gardens, the warmth and long history of this town draw you in. The Lemon Leaf Cafe seems to be a great stop for lunch and, if you are a fellow book lover stop by The Book Plate-a used book store. Chestertown is just around an hour and a half from Baltimore, Washington D.C. or Philadelphia and is another spot for weekend wanderings.

Havre de Grace: This small town also resides on the water, back across the bay (on the Sykesville side), and is less than an hour from Baltimore and a bit more from Philly. Havre de Grace lost the vote to become the nation's capital by one vote in 1789 and has, therefore, kept its small town appeal. The oldest building in town, The Roger's House was built around 1788 and is still standing after a British burning of town in 1813. The shopping district is located along Washington and St. John Streets with some more along Franklin. Antique stores and restaurants line these streets and offer up a feeling of older days. JoRetro Vintage Market is one place I want to be- I can feel the Pyrex in my hands! Lyons Pharmacy also seems to be a classic to enjoy. After getting my shop on, I would grab a bite at The Promenade Grill before strolling along the promenade itself to the Havre de Grace Decoy Museum and the Concord Point Lighthouse. If shopping isn't your thing, nearby Susquehanna State Park has easy hiking trails with beautiful views and plenty of history. The Union Hotel Restaurant & Tavern is a trip worth taking for dinner or just the ambiance of an 18th century restaurant. The final takeaway for this trip should be some pastries from Les Petits Bisous.

Berlin: One of the best and most charming has been saved for last. This town, Berlin, near Ocean City and Assateague Island, has so much to see and do. The town is such a beauty that it served as the backdrop for 2 movies- Runaway Bride and Tuck Everlasting. There are more than a handful of restaurants with high scoring reviews. The Globe is an old theater turned into a restaurant offering live music and an art gallery, on top of yummy food. The Blacksmith is a gastropub with a hipster vibe and eclectic menu and if you like to try some local liquid flavor be sure to check out events at Burley Oak Brewing Company or check the menus at local restaurants. Drummer's Cafe, inside the Atlantic Hotel, has been attracting tourists and locals for over 100 years with dining classics. There is a great little shopping district full of boutiques and antiques, and art galleries. The town is the host to many events, such as movies, live music and the annual Berlin Bathtub Races. The Atlantic Hotel is a choice for staying overnight and, nearby, Ocean City has hotels and rentals for every budget and taste. Berlin is a small town with big appeal!

If you are looking for getaway ideas and need some suggestions, or you are ready to book your next vacation, please contact us at Stowaway Travels.


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