10 Towns In Maryland With The Best, Most Lively Main Streets
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Jamie Alvarenga
Author
Looking for a charming town in Maryland to visit? We’ve got plenty of those. However, the following 10 downtown spots are sure to help you make the most of your time. Filled with restaurants, events, galleries, and much more, these 10 towns in Maryland have the best, most lively main streets.
Maryland's capital is filled to the brim with delicious eateries, shops, and waterfront views. If seafood is your pleasure, then the restaurants found in this downtown area are for you.
This cool small town has an abundance of pride. Folks are especially happy to live here because of the fun events hosted throughout the year. There's almost always something going on.
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Frederick is full of charm year-round and it especially comes to life during the holiday season. Shop til you drop at the unique boutiques and take in the views along the promenade.
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Along with a plethora of shops and eateries, St. Michaels also has a few charming bed & breakfasts if you want to stay for the weekend. The downtown area is perfect for a summer day trip.
Parts of Ellicott City's Main Street are still recovering after the recent flooding but many shops are now open and awaiting your patronage. Be sure to check out First Fridays when they return, as well as Girl's Night Out.
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A walk through this downtown area is like taking a step back in time. Be sure to also check out Chestertown in autumn, during the Harry Potter festival. It's simply put, magical.
This little town has quite a few unique shops and the promenade is perfect for a warm-weathered stroll. The downtown area also lights up during certain holidays and occasions.
The most recent winner of America's coolest small town title, Sykesville is growing to be one of the best new spots to visit and live. You're sure to find something at the farmers market before chowing down at a local eatery.
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This western Maryland town has a unique look, and the events bring the locals in droves. History is abundant here and you'll love seeing the old buildings and railroad up close.
Moving even further west, we come to Oakland. The downtown area is lined with quaint businesses while the events are worth visiting. Be sure to especially checkout the Autumn Glory Festival and Winterfest.
Better get started on visiting these lovable main streets. For a charming town bucket list, click here! 🙂
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