8 Best Maryland Towns For A Winter Getaway

Maryland transforms into a cozy winter wonderland each year, offering travelers a mix of snowy mountain escapes, historic small towns, and quiet coastal towns. Starting in the Appalachian foothills in the west and stretching to the quiet beaches of the Eastern Shore, these towns provide the perfect backdrop for winter activities that suit every traveler. These Maryland towns show that winter can be full of adventure, relaxation, and seasonal character waiting around every corner.

Oakland

Located near the Allegheny Mountains, Oakland has no shortage of winter weather to enjoy. Nicknamed "The Snowiest Town in Maryland," Oakland is well-positioned for your winter outdoor activities. Skiers and snowboarders are about 20 minutes away from Wisp Resort, Maryland's only four-season ski resort. Deep Creek Lake also provides an abundance of outdoor thrills with plenty of trails open for snowshoeing and cross-country skiing. For those who enjoy history, the Oakland B&O Railroad Museum takes visitors through the town's railroad past through artifacts and displays. During the winter, Oakland's main streets fill with photo ops, giving visitors the chance to snap social media photos. Visitors taking a trip during February will also get the opportunity to enjoy the town's Winter Fest, which includes horse-drawn carriages, live music, and store specials.

Rock Hall

Located along Chesapeake Bay, Rock Hall offers a quiet winter retreat with a strong coastal identity. While the summer draws sailors and kayakers, the winter reveals calm waterfront views suited to relaxation and reflection. Visitors can stroll along Rock Hall Harbor, watching migratory birds and winter sunsets reflected across the icy shoreline. The Eastern Neck National Wildlife Refuge nearby also remains open in winter, offering trails that are well-suited for spotting bald eagles and other seasonal wildlife.

Stay warm at The Rock Hall Brewing Co. during the colder months, with beers inspired by the town and live performances. Cozy bed-and-breakfasts like Inn at Huntingfield Creek and Getaway Cottages create a relaxed setting for a romantic or low-key getaway. Winter bird walks and birding events around Rock Hall and Eastern Neck give nature lovers another reason to visit during the colder months.

Snow Hill

Snow Hill lives up to its name during winter. The town sits along the Pocomoke River, surrounded by snow-dusted forests that turn the area into a quiet escape. Outdoor enthusiasts can explore Pocomoke River State Park, where winter hiking and photography are especially rewarding thanks to the park’s calm scenery and wildlife.

In town, visitors can explore cozy cafes like Fika Coffee Roasting, which offers warm and locally sourced coffee drinks. The Julia A. Purnell Museum provides a look into the area’s history through quilts and folk art, making it a great indoor stop on chilly days. Snow Hill also marks the season with festive lights and community gatherings that make it feel straight out of a holiday movie. To bring the season alive, Snow Hill also celebrates the holiday season with the Snow Hill Christmas Parade, a favorite activity for locals and visitors alike.

Frostburg

Aptly named, Frostburg turns into a lively mountain town once the snow starts to fall. Set in western Maryland, it is surrounded by Appalachian views and plenty of opportunities for winter adventure. Outdoor lovers can explore the Great Allegheny Passage, a well-known trail that remains open for winter hiking and cross-country skiing. When the temperatures drop, the crisp mountain air and snowy hills create an inviting setting for a cold-weather escape.

Downtown Frostburg offers a varied mix of locally owned locations to explore. Grab a drink and a steak at Sand Springs Saloon & Steakhouse, a laidback restaurant inspired by all things Western. It is a family-owned brewery that embodies Frostburg's spirit. The Thrasher Carriage Museum provides a cozy indoor retreat, displaying antique carriages and sleighs. Each December, the town hosts its Storybook Holiday Festival, complete with carriage rides, Christmas carols, and family-friendly activities that bring a touch of nostalgia to the frosty season.

Thurmont

Surrounded by rolling hills and forested parkland, Thurmont is one of Maryland’s best winter hideaways for nature lovers. The nearby Catoctin Mountain Park and Cunningham Falls State Park are especially eye-catching in winter, offering snow-covered trails for hiking and winter photography. Visitors can also see the frozen waterfall at Cunningham Falls, a favorite winter sight for locals.

Downtown Thurmont has an inviting main street, with local diners and gift shops like Thurmont Main Street Arts & Gifts, located on Water Street, that gives you the perfect place to start your downtown adventure. Winter events like Small Town Christmas on Main Street fill the town with twinkling lights and festive spirit. The nearby Catoctin Furnace Historical Society offers tours during select weekends, giving visitors a glimpse into the area’s industrial history while staying warm indoors. With plenty of opportunities to explore the outdoors, Thurmont offers a balance for those who enjoy a more cozy winter experience.

Chestertown

Located on the banks of the Chester River, Chestertown shows off its timeless character during winter. Its cobblestone streets and colonial-era buildings look especially appealing under a dusting of snow. Visitors can enjoy quiet walks along the waterfront or admire the historic architecture of Washington College and The Custom House. For a cozy afternoon, step into one of the town’s cafés or wine bars in the historic district, like Casa Carmen, for comfort food and conversation.

The town’s arts scene continues year-round, with winter concerts and gallery openings at the Garfield Center for the Arts. Chestertown’s A&E Art Walks and winter markets showcase regional artists and makers, adding to the festive atmosphere. The slower pace of the season makes it the perfect time to enjoy this Eastern Shore town without the summer crowds or heat.

Berlin

Voted one of “America’s Coolest Small Towns,” Berlin is just as appealing in winter as it is in summer. Historic downtown turns into a festive scene, filled with twinkling lights and cozy storefronts. Visitors can browse local boutiques like Victorian Charm for unique finds, sample hot drinks at Cafe Berlin, and enjoy winter comfort food at the historic Atlantic Hotel Bistro Bar.

Nature enthusiasts can venture to nearby Assateague Island, where wild ponies roam along the snowy beaches, offering a rare winter sight. Berlin’s Ice Ice Berlin and Tree Lighting brings locals and tourists together for a cheerful celebration with carriage rides, holiday music, and a giant Christmas tree downtown. Strolling the streets or warming up in a local café gives visitors a real sense of small-town winter life.

Boonsboro

At the foot of South Mountain, Boonsboro provides a calm winter retreat steeped in history. Visitors can explore nearby Greenbrier State Park, which offers hiking trails open year-round, perfect for enjoying Maryland’s crisp winter air. The snow-dusted hills surrounding the town provide postcard-style views ideal for photography or taking some time away from the city.

Downtown Boonsboro is full of historic character, with cozy restaurants like Branded Chophouse, which offers delicious steak plates. Book lovers can visit Turn the Page Bookstore, owned by the husband of author Nora Roberts, and stop for a warm meal at Branded Chophouse. The town also embraces the holiday spirit with events like Boonsboro’s Olde Tyme Christmas, featuring tree lighting, caroling, and festive treats.

Ellicott City

Along the Patapsco River, Ellicott City offers an inviting winter setting with its historic stone buildings and hillside streets. Visitors can explore Patapsco Valley State Park, which stays open year-round for winter hiking and overlooks of frozen waterfalls and icy river views. When snow falls, Main Street’s architecture looks straight out of a storybook.

The town’s boutiques and restaurants, like Manor Hill Tavern, make it an appealing cold-weather destination. Enjoy a warm meal at The Trolley Stop or shop for finds at the Antique Depot. During the holidays, Ellicott City glows with lights and festive window displays for the Midnight Madness & Tree Lighting shopping event, where live music and hot cocoa stands add to the winter cheer.

Winter Getaways in Maryland

If you are seeking the thrill of snow sports, the quiet of a historic town, or the festive energy of holiday events, Maryland offers a variety of winter getaways. Mountain towns such as Oakland and Frostburg pair well with Eastern Shore communities like Rock Hall and Berlin, and each destination provides its own activities and cozy appeal that make cold-weather travel enjoyable. Exploring these small towns allows visitors to experience local culture, seasonal traditions, and varied landscapes while avoiding crowded tourist spots. Winter in Maryland is not just about escaping the chill but also about discovering intimate moments, noticing the details of seasonal scenery, and creating memories in towns that feel welcoming and authentic. These towns offer a mix of adventure, relaxation, and Maryland character.