Winning Winter Events

By Heather Cisar



Featured Places

men drinking beer at bar
Photo By: Visit Baltimore
FeBREWary to celebrate Maryland Craft Beer Lovers Month

1 FeBREWary

FeBREWary 2020 (Events and dates TBD)
FeBREWary is Maryland’s official month-long celebration of craft beer, and with craft brew events on tap across the state, it’s the perfect time for a beer lover's getaway. Breweries, ale houses and brew pubs are in full swing, so head to your favorite Maryland vacation destination and expand your brew I.Q. with a new style of beer from a local craft brewer, or cozy up with a tall mug of an old favorite in a bit of Maryland you've yet to explore. From the mountains to the beach, FeBREWary in Maryland is the perfect opportunity to hoist a pint with good friends in great places.
More info...

Frederick Douglass Sign Photo By: Clark Vandergrift

2 Black History Month

February 2020 (Events and dates TBD)
The story of the African-American experience in Maryland is the story of America. From the founding of the colony, through the horrors of slavery and the heroism of the Underground Railroad, to the Jazz Age and the thriving contributions to the sciences, arts and culture of today: the Maryland African-American story is one of perseverance, courage and triumph.

More info...

A Couple Enjoy Lunch at Firestones in Frederick Photo By: Natural Artistry

3 Valentine's Day in Maryland

2020 events and dates TBD
Indulge that special someone with a little romantic Maryland magic. You’ll LOVE these ideas for celebrating the month of "amour."
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Picture of a powerboat on the water.

4 Seaside Boat Show, Ocean City

2020 dates TBD
The #1 indoor Boat Show on the Eastern Shore, featuring over 350 boats, electronics, dock builders, boat lifts, crafts, canvas, fishing rods, fishing tackle, paddle boards, artists, and food vendors.

Oakland Winterfest

5 Oakland Winter Fest

2020 dates TBD
Winterfest is always held President's Day weekend in Oakland, located in Western Maryland. Events include ice carving demonstrations, illuminated ice sculptures, interactive sculptures, store specials, vendors/crafters, carriage rides, exceptional dining and more!

Maryland Wine Month

6 Maryland Wine Month

March 2020 (Events and dates TBD)
This March, both connoisseurs and novices of wines can celebrate during Maryland Wine Month with a jam-packed calendar of events and eight wine trails.
More info....

couple dining Photo By: Petit Louis Restaurant

7 Winter Restaurant Weeks

2020 events and dates TBD
From picking crabs at a table to haute cuisine, Maryland has that and everything in between. Many communities and their local restaurants sponsor a week-long experience so that you can eat to your heart's content - at a great price.  
More info...

Related Articles & Guides


About Winter

Skiers at Wisp
Top Things to do in Winter

Fun never hibernates in Maryland! So dig out the boots, gloves and hats, and head to Western Maryland because the slopes are beckoning you to come out and play.  ...


Outdoor Ice Skating

Join Family and Friends for Outdoor Ice Skating Fun.


girl sipping cocoa
Hot Cocoa in Maryland

 A cool winter day in Maryland is perfect for enjoying a cup of hot chocolate. 



Winter sports are hot in Maryland. Try snowshoeing in the mountains out West.
Cross Country Skiing

The following Maryland State Parks offer cross country skiing ...