8 Best Destinations For A Winter Vacation In Maryland

Winter in Maryland is a season of magic, where picturesque towns and scenic landscapes come alive with seasonal charm. Whether you’re seeking thrilling adventures, cozy getaways, or cultural explorations, a winter vacation in Maryland has something for everyone. From gliding down the snowy slopes at Wisp Resort in McHenry, surrounded by the tranquil beauty of Garrett County, or savoring the maritime charm of St. Michaels with its seasonal seafood feasts.

Maryland’s diversity means you can enjoy everything from ice fishing on Deep Creek Lake to walking through Cumberland’s Victorian streets, steeped in history. Whether it’s a family ski trip, a romantic retreat, or a quiet escape into nature, Maryland delivers unforgettable winter moments.

Chestertown

Chestertown, a charming colonial town along the Chester River, becomes a tranquil haven in winter. Downtown Chestertown is even more appealing with fewer crowds observing its beautifully preserved 18th-century buildings. Visit the Bookplate, a beloved local bookstore, or pick up handcrafted goods at Twigs and Teacups. The Garfield Center for the Arts often hosts winter performances, from plays to musical events, adding cultural warmth to chilly evenings. Afterward, you can pop into Evergrain Bread Company for artisanal pastries and a hot cup of coffee. Winter is also a great time to enjoy Chestertown’s craft breweries and wineries, such as Crow Vineyard & Winery, located just a short drive away.

The Chester River is stunning in winter, with its glassy surface reflecting the stark beauty of the season. Take a riverside walk or enjoy birdwatching at Wilmer Park, where migratory birds frequent the area. The town also hosts seasonal markets and events, such as the Farmers’ Market, where you can find fresh produce and local crafts. Meanwhile, the Brampton Inn, a charming 1860s bed-and-breakfast just outside town. Surrounded by sprawling grounds, it has fireplaces, warm décor, and gourmet breakfasts. Another excellent option is The White Swan Tavern, located in the heart of downtown. This historic inn combines colonial charm with modern comfort, making it a perfect winter retreat.

Wisp Resort- McHenry

For those seeking a winter adventure, Wisp Resort in McHenry is the perfect destination. Known for its ski slopes and snowy landscapes, it attracts both beginners and seasoned winter sports enthusiasts. The resort features over 30 ski trails, making it ideal for skiers and snowboarders. Additionally, Snow tubing down the mountain is a favorite for families and groups, and the resort’s snowshoeing and cross-country skiing trails provide a quiet way to explore the winter wonderland. For something unique, try ice skating on the resort’s outdoor rink. Lodging options at Wisp Resort include cozy cabins and slopeside rooms.

The town of McHenry has its own charm. Grab a hot Crab meal at the Pine Lodge Steakhouse or a warm drink at Moonshadow Café. For those looking for a quieter winter experience, take a stroll along Deep Creek Lake, just minutes from the resort. The lake’s still waters reflect the surrounding snow-covered scenery, creating a peaceful atmosphere.

The Inn At Huntingfield Creek - Rock Hall

Rock Hall transforms into a serene winter getaway along Maryland’s Eastern Shore. The centerpiece of this coastal gem is The Inn at Huntingfield Creek, a cozy accommodations ideal for curling up after a day of exploration. Take advantage of the inn's spa services or have a quiet evening with a book by the fire. There is also a heated saltwater pool to keep the cold at bay in the evenings. The innkeepers often organize events like wine tastings or cooking demonstrations, adding a personal touch to your stay.

The Chesapeake Bay is stunning even in colder months, with misty mornings and breathtaking sunsets. Bundle up for a peaceful stroll along the shoreline or explore the nearby Eastern Neck National Wildlife Refuge. The refuge offers winter birdwatching opportunities as migratory birds, including tundra swans and bald eagles, make their seasonal appearance. The town itself has a warm, welcoming vibe in winter. Local shops, like Java Rock, invite you to taste handmade goods and warm drinks.

St. Michaels

Another town on the eastern banks, St. Michaels is a delightful winter getaway. Winter is an ideal time to explore the Chesapeake Bay Maritime Museum, which remains open year-round. Visitors can learn about the area’s nautical heritage and enjoy views of the harbor without the summer crowds. For shopping enthusiasts, Talbot Street is the heart of the town, lined with boutique stores and local artisan shops. Don’t miss a visit to Skipjack's, which serves warm seasonal treats like warm donuts and gourmet coffee in addition to their famous sweets. You may also savor a warm bowl of soup at Ava’s Pizzeria & Wine Bar. The local wineries and breweries, such as St. Michaels Winery, offer tastings of their winter selections.

St. Michaels also hosts seasonal events like the annual “Christmas in St. Michaels,” featuring festive parades and holiday markets. Accommodations in town enhance the winter vibe. The Inn at Perry Cabin is a luxurious option, known for its elegant rooms, fireplaces, and views of the bay. Another cozy choice is the St. Michaels Harbour Inn, Marina & Spa, with comfortable rooms and spa services to help you relax.

Gaylord National Resort & Convention Center - Oxon Hill

Oxon Hill, 21 minutes from Washington DC on the Potomac River, is a vibrant winter getaway centered around the Gaylord National Resort & Convention Center. This sprawling resort becomes a winter wonderland, attracting families, couples, and solo travelers alike. During the holiday season, the resort hosts its iconic ICE! Exhibit, featuring intricately carved ice sculptures and interactive experiences. Guests can enjoy ice slides, themed displays, and the magical feeling of walking through a frozen world. For more family-friendly fun, the resort presents activities like gingerbread decorating, scavenger hunts, and nightly light shows in the atrium.

Beyond the resort, Oxon Hill’s National Harbor area buzzes with winter activities. The Capital Wheel provides stunning views of the Potomac and nearby landmarks, especially when the winter skies are clear. The MGM National Harbor adds an extra layer of excitement. This entertainment complex features live performances, fine dining, and a luxurious casino.

Oakland

Oakland is a place where winter feels magical in the Allegheny Mountains. Oakland’s winter magic begins at Swallow Falls State Park, where icy cascades create a breathtaking sight. A brisk hike to Muddy Creek Falls rewards visitors with stunning frozen waterfalls surrounded by snow-covered hemlocks. The nearby Deep Creek Lake area provides opportunities for snowshoeing, cross-country skiing, and scenic drives along the frosty shoreline.

Downtown Oakland is a cozy retreat after outdoor excursions. Wintertime events like the Winter Fest bring the community together with ice sculpting, local crafts, and horse-drawn sleigh rides through the town’s historic streets. Meanwhile, Haley Farm Inn and Retreat Center provides a 65-acre escape with a focus on relaxation and wellness, making it ideal for couples or solo travelers seeking peace.

Cumberland

Cumberland, "Queen City," brings to spend winter on the western edge of Maryland. Begin your winter visit with a ride on the Western Maryland Scenic Railroad. The train winds through snow-blanketed landscapes, creating a postcard-worthy experience. Furthermore, Rocky Gap State Park provides trails for snowshoeing and winter hiking. The calm of Lake Habeeb, framed by frosted trees, is ideal for nature photography or quiet reflection.

Downtown Cumberland is a lively hub of local culture and history. Winter events, such as the Cumberland Ice Festival, feature intricate ice sculptures and family-friendly activities. Local eateries add warmth to your visit. Crabby Pig serves hearty Maryland-style seafood, while Ristorante Ottaviani is a favorite for authentic Italian dishes in a cozy setting. Stay at Fairfield Inn & Suites which delivers modern amenities and easy access to nearby attractions, ensuring a comfortable stay.

Annapolis

Annapolis, Maryland’s capital, converts into a charming winter retreat with its waterfront views and historic streets along the Chesapeake Bay. The Maryland State House, the oldest state capitol still in use, is a must-see. Winter brings fewer crowds, making it an ideal time to explore landmarks like the William Paca House and Garden. For those drawn to the water, take a winter boat tour on the Chesapeake Bay. While the air may be crisp, the stunning views of the harbor and iconic Naval Academy are worth it. Speaking of the U.S. Naval Academy, a drop-by to its museum provides insight into the town’s maritime history.

Annapolis’ local dining scene is buzzing even in winter. Warm up with fresh seafood like oysters and crabs at Carrol’s Creek Café or savor local flavors at Galway Bay Irish Pub. Winter extravaganzas like the Midnight Madness shopping events fill the air with excitement. Visitors can enjoy light displays, live music, and local artisans showcasing their work.For a cozy stay, consider the Historic Inns of Annapolis, where colonial houses welcome visitors to spend their vacation amid period-style furnishings, decorative fireplaces, and 4-poster beds.

Final Thoughts

Envision yourself wandering the festive streets of Annapolis, where colonial architecture and waterfront views create a magical winter backdrop. Or imagine gliding down the slopes at Wisp Resort in McHenry, surrounded by frosted pines. History enthusiasts can stroll through Cumberland’s canal trails and admire its Victorian charm while Oxon Hill’s Gaylord National Resort dazzles with its holiday lights and indoor winter wonderland. Every corner of Maryland shines in its way, whether through vibrant festivals, charming local shops, or breathtaking natural beauty. Winter vacation in Maryland is an experience to have in the United States.