Fun Weekend Trips in Maryland to Shake Off the Winter Blues
Who says you can’t visit Ocean City in the winter? My family loves to hit the beach during the off-season!
When winter feels endless and the kids are climbing the walls (or maybe you are!), it's time for a little adventure. Luckily, Maryland has plenty of driveable destinations perfect for a quick weekend getaway. Whether you’re seeking cozy family fun, a change of scenery, or something active to burn off those post-holiday calories, these spots will help you shake off the winter blues!
Deep Creek Lake, MD
Drive Time: ~3 hours from Columbia, MD
Why Go: Maryland’s winter wonderland! Deep Creek Lake offers skiing, snowboarding, and tubing at Wisp Resort, plus cozy cabin rentals where you can unwind by the fire. Families will love the chance to go snowshoeing or enjoy a scenic winter hike at Swallow Falls State Park.
St. Michaels, MD
Drive Time: ~1.5 hours from Columbia, MD
Why Go: This charming Eastern Shore town is the perfect escape for a laid-back winter weekend. Take a stroll along the waterfront, visit the Chesapeake Bay Maritime Museum, or cozy up at a B&B. Many local restaurants serve fresh oysters and crab, even in winter.
Ocean City, MD
Drive Time: ~2.5 hours from Columbia, MD
Why Go: Sure, it’s quieter in the winter, but that’s part of the charm! Take a walk on the nearly deserted boardwalk or visit the indoor amusements at Jolly Roger. Bonus: Off-season rates make this an affordable family getaway.
Annapolis, MD
Drive Time: ~40 minutes from Columbia, MD
Why Go: Maryland’s capital is great for a quick winter trip! Explore history with the kids at the U.S. Naval Academy or wander downtown’s cobblestone streets filled with shops and restaurants. For family-friendly fun, visit the indoor trampoline park at Sky Zone or check out Pirate Adventures on the Chesapeake.
Frederick, MD
Drive Time: ~1 hour from Columbia, MD
Why Go: This picturesque town blends history, shopping, and family-friendly fun. Stroll along Carroll Creek Park for some fresh air, explore the kid-friendly exhibits at the Roads and Rails Museum, or enjoy a chocolatey treat from The Perfect Truffle. Winter festivals often pop up, so check the calendar before you go!
Assateague Island
Drive Time: ~2.5 hours from Columbia, MD
Why Go: Bundle up and visit the wild ponies! This peaceful barrier island is a unique winter destination for families who enjoy nature. Take a wildlife hike or bike ride and enjoy the beauty of the Atlantic Coast without the summer crowds.
Baltimore, MD
Drive Time: ~30 minutes from Columbia, MD
Why Go: A city staycation packed with family fun! Spend the day at the National Aquarium, explore the Maryland Science Center, or lace up your skates at the Pandora Ice Rink in the Inner Harbor. For a dose of culture, check out the kid-friendly workshops at the Walters Art Museum.
Cumberland, MD
Drive Time: ~2.5 hours from Columbia, MD
Why Go: Nestled in the Appalachian Mountains, Cumberland offers stunning winter landscapes and outdoor activities. Take the kids on a scenic ride aboard the Western Maryland Scenic Railroad or stay the weekend at Rocky Gap Resort.
National Harbor
Drive Time: ~1 hour from Columbia, MD
Why Go: This destination offers a mix of outdoor and indoor activities perfect for families. Take a ride on the Capital Wheel, explore the shops, or enjoy a magical evening at ICE!, a holiday-themed ice sculpture exhibit.
Escape the Winter Rut
Maryland may be small, but it’s packed with fun destinations. So grab the kids, bundle up, and hit the road—your next adventure is just around the corner!
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