15 Best Small Towns to Visit in Maryland

Prepare to be enchanted by Maryland, a state often celebrated for its bustling cities and stunning Chesapeake Bay, but whose true heart lies within its charming small towns. Venture beyond the usual tourist trails, and you will discover a tapestry of history, natural beauty, and authentic local culture that truly captivates. From the serene mountainscapes of Western Maryland to the historic maritime villages lining the Eastern Shore, each town offers a unique slice of Americana, brimming with stories, flavors, and experiences waiting to be uncovered.

This guide invites you on an unforgettable journey through 15 of Maryland’s finest small towns, promising not just sights but genuine connections. To make the most of your adventure, consider visiting during the spring or fall when the weather is mild and the landscapes are at their most vibrant, offering perfect conditions for exploring. A car is highly recommended for navigating these diverse locales, allowing you the freedom to discover hidden gems at your own pace. Get ready to embrace the charm and quiet beauty of the Old Line State!

Thurmont, Maryland

Nestled at the foot of the Catoctin Mountains, Thurmont is a gateway to outdoor adventure and presidential history. What truly makes this town special is its proximity to Catoctin Mountain Park and Cunningham Falls State Park, offering a natural playground for hikers, campers, and nature enthusiasts. You can expect to spend your days exploring miles of scenic trails, discovering cascading waterfalls, and picnicking amidst lush forests.

Don’t miss the opportunity to visit the Catoctin Mountain Park Visitor Center to learn about the area’s rich ecology and history, including its connection to Camp David, the presidential retreat. The town itself offers a quaint main street with local shops and eateries, providing a cozy base for your explorations. Families will particularly enjoy the accessible trails and the natural beauty, while solo travelers and couples can find tranquility in the serene mountain environment. The history here is subtle but significant, tied to the natural landscape and the quiet presence of national importance.

Berlin, Maryland

Voted “America’s Coolest Small Town,” Berlin exudes a charm that feels straight out of a movie set – and indeed, it has been! This vibrant town, just a short drive from Ocean City, offers a refreshing contrast to the bustling beach scene. What makes Berlin unique is its beautifully preserved Victorian architecture, independent boutiques, art galleries, and a thriving culinary scene. You can spend hours strolling along Main Street, popping into eclectic shops, admiring the historic buildings, and perhaps catching a live music performance at one of the local venues.

The town often hosts special events, from farmers markets to holiday celebrations, adding to its lively atmosphere. History buffs will appreciate the town’s commitment to preservation, while art lovers will find inspiration around every corner. Berlin is perfect for couples seeking a romantic getaway, solo travelers looking for a quaint escape, and families who enjoy exploring charming downtowns and unique shops.

Hampstead, Maryland

Hampstead, a quintessential small town in Carroll County, offers a peaceful retreat with a strong sense of community and a rich agricultural heritage. Its uniqueness lies in its quiet, unassuming charm and its connection to the surrounding farmlands. Visitors can expect a relaxed pace, where the main attractions include exploring local parks, visiting a pick-your-own farm during harvest season, or simply enjoying the tranquility of the countryside.

The town hosts several community events throughout the year, such as farmers markets and holiday parades, which are excellent opportunities to experience local life. Hampstead is ideal for families looking for a safe, wholesome environment, and for anyone seeking a break from the hustle and bustle of city life. History here is found in the older homes and the stories of generations of farming families, providing a glimpse into Maryland’s rural past.

Crisfield, Maryland

Crisfield, known as the “Seafood Capital of the World,” is a charming, albeit rustic, waterfront town on the Eastern Shore. Its unique identity is inextricably linked to the Chesapeake Bay and its bountiful seafood industry. Here, you can expect an authentic maritime experience, from watching working watermen bring in their daily catch to savoring the freshest crabs and oysters imaginable.

A highlight is a boat trip to Tangier Island or Smith Island, two remote island communities that offer a glimpse into a unique way of life. The Crisfield Historical Society Museum provides insight into the town’s rich past. This destination is a must-visit for seafood lovers, those interested in maritime culture, and anyone looking for an unpretentious, real-deal coastal town. Families will enjoy the boat trips, while history and food enthusiasts will find plenty to explore.

Eastport, Maryland

While not a small town itself, Eastport is a distinct maritime district of Annapolis that feels like its own charming village, separated by a bridge and a world away from the bustling state capital. What makes Eastport unique is its deep nautical roots, vibrant maritime community, and stunning waterfront views. You can expect to see countless sailboats, yachts, and working boats, and immerse yourself in the sailing culture. Explore the Eastport Yacht Center, enjoy delicious seafood at waterside restaurants, or simply watch the boats go by.

The “Bridge of Sighs” (the Spa Creek Bridge) connecting Eastport to downtown Annapolis is iconic. Eastport is perfect for sailing enthusiasts, foodies, and anyone who loves a picturesque waterfront setting. Couples will find it romantic, and solo travelers can enjoy the relaxed atmosphere. Its history is tied to Annapolis’s maritime heritage, offering a more laid-back, authentic naval experience.

Ocean City, Maryland

Ocean City, Maryland, is a lively resort town renowned for its expansive beaches, iconic boardwalk, and endless entertainment options. While it can be bustling, its core charm as a classic American beach town is undeniable. What makes Ocean City unique is its vibrant energy, offering something for every type of traveler.

You can expect sun-soaked days on the beach, thrilling rides at amusement parks, delicious boardwalk treats like Thrasher’s Fries and Fisher’s Popcorn, and lively nightlife. The 10-mile stretch of beach is perfect for swimming, sunbathing, and surfing. Families will find an abundance of kid-friendly activities, while groups of friends can enjoy the nightlife and water sports. Its history as a resort destination dates back to the late 19th century, evolving into the dynamic coastal hub it is today.

Havre de Grace, Maryland

Havre de Grace, nestled at the mouth of the Susquehanna River where it meets the Chesapeake Bay, is a picturesque maritime town rich in history and natural beauty. Its unique appeal lies in its strategic location, offering stunning waterfront views, a charming historic downtown, and a strong connection to lighthouses and decoys. You can expect to explore the iconic Concord Point Lighthouse, Maryland’s second oldest lighthouse, and visit the Havre de Grace Decoy Museum, showcasing the town’s heritage as a center for waterfowl hunting and decoy carving.

Stroll along the promenade, browse antique shops, and enjoy fresh seafood at local restaurants. The town’s military and maritime history is palpable. It’s a wonderful destination for history buffs, nature lovers, and anyone seeking a tranquil yet engaging waterfront experience. Families will enjoy the lighthouse and promenade, while couples can appreciate the scenic beauty and charming atmosphere.

Monkton, Maryland

Monkton, a small, unincorporated community in northern Baltimore County, epitomizes rural tranquility and equestrian charm. What makes Monkton unique is its setting along the scenic Northern Central Railroad Trail (NCR Trail), a popular rail-trail ideal for biking, walking, and horseback riding. You can expect to enjoy peaceful outdoor activities, often seeing horses grazing in nearby pastures, and experience the quiet beauty of Maryland’s countryside.

The NCR Trail itself is the main attraction, offering miles of flat, well-maintained path that follows the historic railroad line. There are a few local businesses, including a charming general store and a country pub, that embody the area’s relaxed pace. Monkton is perfect for outdoor enthusiasts, cyclists, and anyone looking for a serene escape into nature. It’s an excellent spot for families to bike together and for solo travelers to find quiet reflection.

Oakland, Maryland

Oakland, the seat of Garrett County, is a charming small town nestled in the heart of Maryland’s scenic Appalachian Mountains. Its uniqueness stems from its proximity to Deep Creek Lake and numerous state parks, making it a hub for outdoor recreation in all seasons. You can expect to explore a historic downtown with Victorian architecture, browse antique shops, and learn about the area’s railroad and logging history.

The Garrett County Historical Museum offers a fascinating glimpse into the past. Beyond the town, adventure awaits with opportunities for hiking, fishing, skiing (at nearby Wisp Resort), and water sports on Deep Creek Lake. Oakland is ideal for outdoor adventurers, families seeking mountain getaways, and history enthusiasts. Its cool mountain climate makes it a refreshing escape, especially in summer.

St Mary’s City, Maryland

St. Mary’s City holds the distinction of being Maryland’s first capital and is now a living history museum, offering a profound journey back to the 17th century. What makes it truly unique is its dedication to recreating the early colonial experience, allowing visitors to step directly into the past.

You can expect to encounter costumed interpreters who bring history to life, explore reconstructed buildings like the State House and Godiah Spray Tobacco Plantation, and even board a replica of The Dove, one of the ships that brought the first European settlers to Maryland. This site is a treasure trove for history buffs, families, and anyone curious about America’s foundational stories. It provides an immersive educational experience, showcasing the daily lives, challenges, and triumphs of early Marylanders.

New Market, Maryland

New Market, proudly known as “The Antiques Capital of Maryland,” is a charming historic town that lives up to its name. Its unique appeal lies in its concentration of antique shops, housed within beautifully preserved 18th and 19th-century buildings that line its main street. You can expect to spend hours browsing through a treasure trove of vintage finds, from furniture and collectibles to unique decorative items.

Beyond the antiques, the town boasts a rich history, evident in its architecture and the stories of its past. New Market is perfect for antique collectors, history lovers, and anyone who enjoys a leisurely stroll through a picturesque town. Couples looking for a unique shopping experience and solo travelers seeking a quiet escape will find it particularly appealing.

Vienna, Maryland

Vienna, a tiny, historic town on the Nanticoke River, offers a glimpse into Maryland’s colonial past and its enduring connection to the waterways. What makes Vienna unique is its remarkably preserved 18th-century architecture and its tranquil, off-the-beaten-path feel. You can expect to find a serene atmosphere, explore historic homes like the Nanticoke River Lighthouse (a replica, but charming), and enjoy views of the river.

The town’s history as a bustling port in colonial times is fascinating, and its quiet streets now invite peaceful reflection. It’s ideal for history buffs, photographers, and those seeking a quiet escape where time seems to slow down. The beauty of the river and the historic architecture provide a sense of timelessness.

Emmitsburg, Maryland

Emmitsburg, nestled in the Catoctin Mountains near the Pennsylvania border, is a town deeply rooted in religious history and educational heritage. What makes Emmitsburg unique is its profound connection to St. Elizabeth Ann Seton, America’s first native-born saint, and the home of Mount St. Mary’s University.

You can expect to visit the National Shrine of Saint Elizabeth Ann Seton, a pilgrimage site that offers a peaceful and contemplative experience, including her historic home and basilica. The town also serves as a gateway to beautiful mountain scenery and is home to the National Fire Academy. It’s an ideal destination for those interested in religious history, quiet contemplation, and a glimpse into higher education in a scenic setting. Families might find the Shrine interesting for historical context, and solo travelers seeking reflection will appreciate the tranquility.

Leonardtown, Maryland

Leonardtown, the county seat of St. Mary’s County, is a charming and historic waterfront town on Breton Bay. Its unique blend of history, arts, and a laid-back Southern Maryland vibe makes it a delightful stop. You can expect to explore a vibrant arts and entertainment district, browse local boutiques and art galleries, and enjoy waterfront views.

The Old Jail Museum offers a peek into the town’s past, while the Leonardtown Wharf provides opportunities for kayaking, paddleboarding, or simply relaxing by the water. The town hosts numerous community events and festivals, showcasing local talent and produce. Leonardtown is perfect for those who appreciate small-town charm, local arts, and a connection to the water. Families will enjoy the wharf activities, while couples can find a relaxed, romantic atmosphere.

St. Michaels, Maryland

St. Michaels, often called “The Town That Fooled the British,” is a picturesque waterfront gem on Maryland’s Eastern Shore, renowned for its maritime history, beautiful harbor, and upscale charm. What makes St. Michaels truly unique is its perfectly preserved historic district, vibrant Main Street, and the world-class Chesapeake Bay Maritime Museum.

You can expect to immerse yourself in nautical history, explore historic homes, browse boutique shops, and dine at exquisite waterfront restaurants. A cruise on a historic skipjack or paddle-boarding in the harbor are popular activities. It’s an ideal destination for couples seeking a romantic getaway, maritime enthusiasts, and anyone who appreciates fine dining and charming small-town ambiance. Its role in the War of 1812 adds a fascinating historical layer.

Plan Your Visit

Maryland’s small towns are truly a revelation, offering an incredible diversity of experiences that cater to every interest. From the rugged mountain trails of Thurmont and Oakland to the tranquil waterfronts of Crisfield and Vienna, and the historic charm of Berlin and St. Michaels, you’ll discover hidden gems that capture the essence of the Old Line State.

This journey through lesser-known locales promises not just picturesque scenery but also deep dives into history, vibrant local cultures, and genuine hospitality. Whether you’re a budget traveler seeking free outdoor adventures or looking to splurge on a luxurious maritime escape, Maryland’s small towns offer flexible options. So, pack your bags, choose your adventure, and prepare to be utterly charmed. These towns are waiting to share their unique stories and create unforgettable memories for you.