6 Serene Towns in Maryland for a Weekend Retreat
Maryland, known as the "Old Line State," borders the nation’s capital and has a diverse geography, ranging from sandy dunes on the Atlantic Ocean to mountainous regions in its western parts. The state played a pivotal role in American history, hosting key events of the Civil War and serving as the birthplace of the national anthem during the Battle of Baltimore in 1814. Maryland's smaller towns offer a quieter and more serene alternative to its larger cities like Baltimore for a weekend retreat. These towns are nestled along waterways or amidst Maryland's countryside for weekenders to enjoy outdoor activities and explore local history.
Saint Michaels
Saint Michaels, Maryland, is on the Eastern Shore of the Chesapeake Bay, with waterways and pretty coastline views. It is often referred to as "the town that fooled the British" due to its role in the War of 1812; one of the town's most celebrated tales. From shipbuilding to oystering, the town’s economy has been influenced by its proximity to the ocean. The Inn at Perry Cabin's setting here prompts calmness, where the rustling of leaves and flow of water command attention—it is the recommended spot for a serene weekend away in Saint Michaels.
The Chesapeake Bay Maritime Museum is a must-visit. Spanning over 18 acres on a waterfront property, visitors can learn about traditional boat-building techniques, the life of a lighthouse keeper, oystering, and crabbing in the bay here. For an experience on the water, board the Sail Selina II. This historic sailing vessel is a hands-on opportunity to learn about sailing, navigation, and the natural beauty of the Chesapeake Bay. In the center of the town, St. Michaels Winery explores Maryland's emerging wine scene. Visitors can sample wines made from locally grown grapes in a friendly setting.
Frostburg
Frostburg is located in the Appalachian Mountains and has a coal mining history. The geography of the town, characterized by rolling hills and forests, provided a bounty of natural resources after its founding in 1812. The architecture within Frostburg is a mix of 19th-century homes and commercial buildings, alongside remnants of the coal mining industry. The town's Hotel Gunter has been a cornerstone of hospitality for over a century. It has spacious rooms and in-house dining options in the historic center of Frostburg.
In Frostburg's historic downtown, Main Street Books is housed in a preserved building with a curated selection of books, including works by local authors and regional history titles. Meanwhile, Tracks and Yaks is an outdoor adventure. This experience involves rail biking along the scenic Great Allegheny Passage. Finally, the Western Maryland Scenic Railroad has steam and diesel-powered train rides from Frostburg to Cumberland, winding through the mountains. Along the way, passengers learn about the history of the railroad.
Berlin
Berlin, Maryland, is a short drive from the Atlantic coast and comprises farmlands, forests, and the meandering tributaries of the Chesapeake Bay. Founded in the 18th century, Berlin's architecture spans two centuries, with 47 buildings in this town on the National Register of Historic Places. On this list, The Inn Berlin Bed and Breakfast is a Victorian estate on 1.5 acres of land. It has comfortable guestrooms and amenities for visitors.
At Assateague State Park, visitors can engage in bird watching, hiking, and kayaking, exploring the unique barrier island ecosystem that supports a variety of wildlife, including the famous wild ponies known to roam the area. Berlin's Mermaid Museum is dedicated to mermaid folklore, art, and environmental conservation. It is an educational journey through the myths and legends of mermaids. The museum also emphasizes marine conservation. A stroll through downtown Berlin on a Sunday morning in May through September will bring you to the Berlin Farmer’s Market. Visitors can enjoy fresh, locally grown fruits and vegetables, handmade goods, and delicious treats while experiencing the hospitality of Berlin.
Thurmont
Thurmont is another Appalachian Mountain town off Highway 15, between Frederick and Gettysburg. The town played a notable role during the Civil War and its natural setting near the Catoctin Mountains draws nature enthusiasts for a long weekend away. While it may not boast luxury, the Super 8 Thurmont is the primary accommodation in the town; it is a convenient and safe base for discovering Thurmont.
Catoctin Mountain Park has a trail system that invites visitors to explore the Catoctin Mountains, with paths leading to vistas, waterfalls, and quiet wooded areas. The park also protects the ecosystems and wildlife of the region. The Thurmont Trolley Trail traces the former Hagerstown & Frederick Railway route with historical markers. This easy, accessible trail winds through the town and countryside for a peaceful walk or bike ride. Lastly, the Roddy Road Covered Bridge and Loy’s Station Covered Bridge are two of Thurmont's most historically significant structures. These covered bridges, dating back to the 19th century, are among the few remaining in Maryland.
Annapolis
Annapolis, Maryland, the state's capital, is known for its well-preserved 18th-century architecture, a testament to the town's significance during the Colonial and Revolutionary periods. As a long-time maritime center, the town has a network of creeks, coves, and inlets. This port town is also home to the U.S. Naval Academy. Located just steps from downtown Annapolis, 134 Prince is a high-end accommodation option with common areas, landscaped gardens, and acquainted guest rooms.
At the William Paca House & Garden, visitors can step back into the 18th century to experience the life and times of William Paca, a signer of the Declaration of Independence. This restored Georgian mansion is set amidst a two-acre pleasure garden. In the bustling waterfront, City Dock, known affectionately as "Ego Alley," has an array of boats, from sleek yachts to historic sailboats. Strolling along the dock, visitors can soak in ocean views, engage with street performers, and perhaps see the Naval Academy midshipmen in formation. Enriching Annapolis's cultural landscape, the Annapolis Symphony Orchestra brings classical music to life under the baton of conductors and features talented soloists.
Chesapeake City
Chesapeake City sits along the banks of the Chesapeake and Delaware (C&D) Canal. This waterway, connecting the Delaware River with the Chesapeake Bay, has been used for maritime navigation and trade since the 19th century, shaping Chesapeake City into a bustling port and a hub of economic activity. As the only hotel located directly on the C&D Canal, The Ship Watch Inn has ten waterfront suites, each with access to an outdoor deck and fire pit.
The C&D Canal Museum is located in the original canal pump house. Through a collection of artifacts, photographs, and models, visitors learn about the canal's construction and its role in regional commerce. For an experiential excursion, Chesapeake City Water Tours has sunset cruises for visitors to watch the sun dipping below the horizon, casting hues over the water. These cruises are an opportunity to learn about the local ecology, wildlife, and historical landmarks from knowledgeable guides. Finally, Pell Gardens is a maintained public garden with landscaped flower beds, shaded benches, and views of the canal. It is a great spot to unwind.
In Summary
Maryland is home to picturesque towns worth escaping to for a weekend. From the historic streets of Saint Michaels, nestled along the Chesapeake Bay, to the Appalachian charm of Frostburg and Thurmont, each town presents its own narrative and attractions that beckon travelers seeking solace. Berlin has historic architecture and a close-knit community feel, whereas Annapolis combines colonial heritage with naval traditions. Still, Chesapeake City, positioned along the crucial C&D Canal, connects visitors with scenic water tours and peaceful gardens. Collectively, these towns in Maryland are must-visits for those desiring a weekend retreat to relax and unwind, away from larger urban centers.
