9 Best Towns In Maryland For A Winter Getaway

The holiday season is upon us, and for some, this is the best time to fulfill those travel plans you’ve had all year long. Maryland is famous for its lively beaches and sunny weather, but rarely is it associated with being a winter destination. Interestingly, this beautiful East Coast state has the potential to grant a remarkable stay during the cold season. Teeming with sprawling parklands, festive winter events, and idyllic towns, there are numerous winter wonderlands to discover in the Old Line State. 

The small towns in Maryland present the perfect setting for a snow season getaway. Shielded from the city crowds and noise, they enjoy a slow pace of life and serene natural surroundings that put you in holiday mode. They also house numerous parklands and nature spaces that turn into gorgeous wintery scenery when it starts to snow. Visitors are spoilt for choice with a long list of adventures, from snow sports and sightseeing opportunities to winter festivals, ensuring there’s never a dull time. So, if you are planning to spend the snowy months on the East Coast, here are towns in Maryland that promise an unforgettable winter getaway. 

Cumberland

Cumberland guarantees winter travelers a fantastic experience in the great outdoors! With over 70,000 acres of public land to explore, this small town transforms into a snow-covered hub for hikers, cross-country skiers, and other adventurers when it snows. There is no better way to experience the winter scenery than to hop aboard the Western Scenic Maryland Railroad. This relaxed journey takes you up the mountainous landscapes in Cumberland’s backcountry, showcasing the beauty of the snow-covered Allegheny Mountain peaks. Those who prefer a quiet spot to sit and enjoy the scenes will find the ideal atmosphere at Constitution Park, which features several pavilions. 

History buffs can spend the day browsing exhibits at the Allegany Museum. The world-class facility preserves the storied past of Allegany County, offering a unique perspective into Appalachian Maryland’s geographical, commercial, and cultural heritage. Finally, you can experience the town’s holiday spirit on the historic downtown corridor and spread some winter cheer during the City Center Tree Lighting Ceremony before spending a good night’s sleep at Hampton Inn Cumberland. 

Oakland

This small town in Garrett County has less than 2,000 residents and hosts multiple state parks and lush natural surroundings, providing winter enthusiasts with endless opportunities. At Deep Creek Lake State Park, you can choose from hiking, ice fishing, cross-country skiing, and ice skating to enjoy the over 1,000-acre park. Alternatively, you can slip into your snowshoes to explore the winter wonderland that is Swallow Falls State Park. When temperatures drop, and the snow begins to fall, the three frozen waterfalls inside the park prove to be a breathtaking scene for explorers. 

For more adventures in the town, Herrington Manor State Park boasts a chill environment with a 53-acre lake within Garrett State Forest. Meanwhile, Oakland has a rich railway heritage that you can learn about at the Oakland B & O Railroad Museum or the Garrett County Historical Museum. To ensure that you’re close to the action, you can stay at the Garrett Inn, which sits about 7 miles from Swallow Falls State Park. 

Flinstone

Home to a modest population of just over 200, Flinstone is riddled with parks, mountains, forests, and lake waters, presenting the ideal environment for a quiet, private winter escape. There is no shortage of things to do for the outdoorsy traveler; the town is home to the sprawling Green Ridge State Forest. Spanning nearly 46,000 acres, it beckons winter hikers, cross-country skiers, campers, and anglers to make the most of its recreational opportunities. Not too far away, you’ll encounter the Rocky Gap State Park, another delightful nature spot with over 3,000 acres of wilderness to discover. 

The park also features a 243-acre reservoir, Lake Habeeb, that is perfect for ice fishing and ice skating. Those who fancy a little exercise to fend off the winter chill can take on the climb to the Polish Mountains. For accommodation, you will find cozy cabins at 7 C’s Lodging, which is a short 10-minute drive from the Rocky Gap State Park. 

Rock Hall

This picturesque bayside town on the Eastern Shore harbors an abundance of winter beauty to explore. Its proximity to popular destinations like Washington D.C., Philadelphia, and Baltimore offers respite from the city noise and fracas. One of the best spots to find accommodation is Osprey Point Inn, which spoils you with gorgeous water views. Stepping outside, the open spaces don’t disappoint, especially at the Eastern Neck National Wildlife Refuge. It hosts a mix of forests, marshes, and grasslands with over 240 bird species to spot, making it a prime location for hikers, skiers, fishers, and birdwatchers. 

Tourists can enjoy local art and museum attractions during the cold season. There are several options to choose from, highlighted by the Rock Hall Museum. Here, you can browse unique artifacts and memorabilia honoring the economic, historical, and cultural heritage of the town. For culinary connoisseurs, you can sample some of the best seafood at the Waterman’s Crab House.  

McHenry

Some of the best winter activities in McHenry involve laidback walks along scenic nature trails through dense woodlands with streams and waterfalls. This modest Garrett County Community packs a punch of winter delights that draw snow sports enthusiasts. Among the highlights is the famous Wisp Resort, home to 32 slopes spanning over 100 acres for snowboarders, snowtubers, and skiers. Besides pleasant accommodations, the resort also boasts the Wisp Adventure Park, where you can learn to ski and snowboard, and the sole Mountain Coaster in the region, with a 1,300-foot-long track.

Bordering Wisp Resort is the sprawling Deep Creek Lake, a prime spot for ice fishing. You can cut a hole in the ice to enjoy an angling experience or put on your ice skates to take advantage of the frozen lake. For winter hikers and snowshoers, Swallow Falls State Park is only 22 minutes away in neighboring Oakland, offering an opportunity to discover a winter wonderland with three frozen waterfalls. 

Ocean City

Most tourists head to Ocean City in the summer, but this scenic coastal town can deliver a remarkable winter vacation. Besides its small population, the crowds are thinner during the snow season, and you have the freedom to explore the beach scenery. You can do this with a lazy stroll along Ocean City Beach, where stunning vistas of the Atlantic Ocean await. If you want a little company, you can climb to the Ocean City Boardwalk, which houses a mix of businesses with street performers along the corridor. Art enthusiasts will feel at home discovering the Art League of Ocean City, a vibrant hub for local artworks. The venue houses rotating exhibits focusing on hands-on pieces by creatives from the area, including pottery and paintings. On the other hand, historians will get a sense of the town’s history at the Ocean City Life-Saving Museum.  After all that, you can relax and rejuvenate at one of the area’s numerous beachside resorts, such as Holiday Inn and Hilton Ocean City. 

Chestertown

Spending winter in one of the oldest towns in Maryland makes for a unique experience with a lot of history to explore. Exploring the historic downtown exposes you to quiet brick sidewalks lined with restaurants, antique shops, and historic structures. There are multiple historical landmarks to check out, including Sumner Hall. The old structure was built by African Americans and portrays their experiences from the Civil War era to the present day. Alternatively, you can stop by the Historical Society of Kent County to explore a collection of artifacts, photographs, and documents chronicling regional history. 

Those looking to explore the outdoor scenery can visit Wilmer Park, which has a relaxed atmosphere and borders the scenic Chester River. This is an excellent venue to unwind and admire the blanket of snow on the little park grounds. When it’s time to call it a day, you can enjoy a unique accommodation experience at the White Swan Tavern, which has a history dating back to the pre-Revolutionary War era. While there, keep the winter chill at bay with a hot cup of tea. 

Annapolis

Annapolis might be Maryland’s capital, but its modest population delights with a small-town vibe while providing experiences for all types of travelers. For visitors with a penchant for the outdoors, Sandy Point State Park offers fun opportunities to discover wintery sceneries. The crowds are conveniently thinner, and snowshoers and cross-country skiers can explore trails like the Blue Crab Trail and Symbi Trail. Alternatively, you can visit Quiet Waters Park and enjoy amenities like nature trails, picnic spaces, and playgrounds. 

As one of the oldest state capitols in the country, the Maryland State House is a popular site for newcomers in Annapolis and remains so during the cold season. Besides exploring old documents, you can admire its snow-covered façade from the surrounding grounds. While there are numerous lodging options in the town, you will wake up to some of the best views at the Annapolis Waterfront Hotel, overlooking the Annapolis Harbor. 

Snow Hill

Blending small-town charm, fun holiday events, and exciting outdoor activities, Snow Hill presents an enticing winter getaway. This quaint community on the banks of the Pocomoke River is riddled with nature spaces that turn into winter wonderlands when it snows. Pocomoke River State invites hikers, snowshoers, sightseers, and ice anglers to make the most of its recreational opportunities. Also, the Pocomoke State Forests looks stunning, with snow covering over 18,000 acres of its expanse. There is a 3.7-mile trail through the woodlands that will be perfect for winter explorers. 

If you’re not exploring the open spaces, you can enjoy a quaint journey back in time at the Furnace Town Historic Site. The site stages old-world reenactments depicting life in Snow Hill during the 19th century. For your lodging, book a stay at the River House Inn and have a comfortable night’s sleep. 

The Takeaway

When temperatures start to drop, and snow begins to fall, exploring the crowd-free small towns in Maryland is an excellent way of appreciating the state’s natural beauty. There is much to see and do, whether planning to revel in the outdoor winter fun, enjoy the beach scenery, or participate in exciting winter destinations.