- Annapolis
Flickr / Orin Blomberg Annapolis just may be the most charming capital city in the US and it’s perfect for shopping year-round, especially during the holidays. Enjoy the greenery adorned to the storefronts, check out the twinkling boat parade, and more!
- Ellicott City
Flickr / Forsaken Fotos This Main Street has been through two massive floods in the last few years but the townsfolk remain strong, with a spirit that cannot be broken. Check out Ellicott City during the holiday season to marvel at the intricate window displays and chow down at the local eateries.
- Frederick
Facebook / Visit Frederick - Maryland Frederick is no stranger when it comes to all things Christmas. Locals and beyond head here through the month of December to shop (and eat) among this delightfully festive atmosphere.
- Berlin
Facebook / Town of Berlin Maryland Horse-drawn carriage ride, anyone? The town of Berlin is full of character and is the perfect spot for a magical day trip. Prepare for lots of unique finds that would make any gift receiver happy.
5.Cumberland
Facebook / Visit Cumberland Maryland Cumberland truly comes to life during the holiday season, starting with the massive Christmas tree lighting. Be sure to shop local at the area stores and don’t forget to grab a bite at the tiny but delectable restaurants.
- St Michaels
Facebook / Christmas in St Michaels It’s hard to find a town more merry than St Michaels. This spot even has a Christmas store that’s open year-round! Head here for a ton of holiday events or to merely shop among the whimsical atmosphere.
- Oakland
Facebook / Town of Oakland, Maryland This little mountain town is a must-visit, especially during autumn and winter. Enjoy the surrounding mountain scenery as you shop among the historic buildings. You never know what you’ll find at Englanders (pictured).
- Sykesville
Facebook / Downtown Sykesville Connection This little town was recently named America’s Coolest Small Town and from there, it’s slowly been gaining more recognition. Head here for one-of-a-kind boutiques, a train-station restaurant, and more.
- Chestertown
Facebook / Downtown Chestertown Association Chestertown is full of shops just waiting to be explored. Enjoy strolling through this area while coming across unique finds.
- Havre de Grace
Facebook / Explore Havre de Grace You’ll find most photos of Havre de Grace depicting its beautiful lighthouse, but the downtown area is where things are really lively. Check out the local stores and swoon over the sparkling decor lining the entire street.
Speaking of the holidays, did you know that Six Flags America transforms into a holiday wonderland during this time of year? Check out Holiday in the Park, a must-see Maryland event!
Flickr / Orin Blomberg
Annapolis just may be the most charming capital city in the US and it’s perfect for shopping year-round, especially during the holidays. Enjoy the greenery adorned to the storefronts, check out the twinkling boat parade, and more!
Flickr / Forsaken Fotos
This Main Street has been through two massive floods in the last few years but the townsfolk remain strong, with a spirit that cannot be broken. Check out Ellicott City during the holiday season to marvel at the intricate window displays and chow down at the local eateries.
Facebook / Visit Frederick - Maryland
Frederick is no stranger when it comes to all things Christmas. Locals and beyond head here through the month of December to shop (and eat) among this delightfully festive atmosphere.
Facebook / Town of Berlin Maryland
Horse-drawn carriage ride, anyone? The town of Berlin is full of character and is the perfect spot for a magical day trip. Prepare for lots of unique finds that would make any gift receiver happy.
Facebook / Visit Cumberland Maryland
Cumberland truly comes to life during the holiday season, starting with the massive Christmas tree lighting. Be sure to shop local at the area stores and don’t forget to grab a bite at the tiny but delectable restaurants.
Facebook / Christmas in St Michaels
It’s hard to find a town more merry than St Michaels. This spot even has a Christmas store that’s open year-round! Head here for a ton of holiday events or to merely shop among the whimsical atmosphere.
Facebook / Town of Oakland, Maryland
This little mountain town is a must-visit, especially during autumn and winter. Enjoy the surrounding mountain scenery as you shop among the historic buildings. You never know what you’ll find at Englanders (pictured).
Facebook / Downtown Sykesville Connection
This little town was recently named America’s Coolest Small Town and from there, it’s slowly been gaining more recognition. Head here for one-of-a-kind boutiques, a train-station restaurant, and more.
Facebook / Downtown Chestertown Association
Chestertown is full of shops just waiting to be explored. Enjoy strolling through this area while coming across unique finds.
Facebook / Explore Havre de Grace
You’ll find most photos of Havre de Grace depicting its beautiful lighthouse, but the downtown area is where things are really lively. Check out the local stores and swoon over the sparkling decor lining the entire street.
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Address: Ellicott City, MD, USAAddress: Frederick, MD, USAAddress: Annapolis, MD, USAAddress: Sykesville, MD 21784, USAAddress: Oakland, MD 21550, USAAddress: Cumberland, MD 21502, USAAddress: Berlin, MD 21811, USAAddress: Saint Michaels, St Michaels, MD 21663, USAAddress: Chestertown, MD 21620, USAAddress: Havre de Grace, Havre De Grace, MD 21078, USA
