Chesapeake City Turns Into A Winter Wonderland Each Year In Maryland

During the holidays, there are a multitude of small towns in Maryland that go all out for the season. And while places like St. Michaels and Berlin get a lot of attention, the following underrated spot is worth exploring. This little canal-side town is truly the best winter town in Maryland, and though it’s charming year-round, it takes on a special tinge of merry during the month of December.

Visit Chesapeake City’s website for more information on all Winterfest of Lights events, which makes this the best winter town in Maryland.

Have you visited this charming waterside town in Maryland? Be sure to also check out these 12 main streets in Maryland that are pure magic during Christmastime.

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Address: Chesapeake City, MD, USA
The OIYS Visitor Center

Best Winter Town In Maryland

October 19, 2019

What other places are the most festive towns in Maryland?

There's a long, long list of Christmas and festive towns in Maryland, each one seemingly more magical than the last. If you're looking for a community that truly indulges in the holiday spirit, then you'll want to head to North Beach or Baltimore, each coastal city adding a beachy breeze to the beauty of the season. Tilghman Island is famous for its annual crab pot tree, and the town of Bethseda has some of the most beautiful garlands and lights on display in the state. Head to Oxon Hill for stunning Christmas lights, or check out the holiday illuminations in Annapolis or Frederick.

What are the best things to do for Christmas in Maryland?

The Winterfest of Lights in Ocean City just might be one of the most popular holiday light displays in Maryland, but we'd also recommend the Sailing Through Winter Solstice event in Frederick or the Brookside Garden of Lights in Wheaton. The Miracle on 34th Street in Baltimore is always worth a visit, and the Lights on the Bay in Annapolis just might make for one of the most magical visuals in the state. These are some of the best places to visit in winter in Maryland.

What kinds of activities can I do in winter in Maryland?

Maryland has some of the best wintertime activities in the nation! Whether you're riding the Western Maryland Scenic Railroad through the snow-covered mountains or viewing more than 600 beautifully decorated Christmas trees at the Festival of Trees, there's truly no end to the fun and excitement. Go ice skating at Quiet Waters Park in Annapolis, or fill up on Baltimore Restaurant Week, where you can indulge in some of the best restaurants in the city for much, much less. Sandy Point State Park makes all sorts of holiday day out of the stunning park, and ice fishing in Deep Creek Lake? A true bucket list experience.