If you are thinking moving to marylandbustling cities like Baltimore and Frederick may come to mind. But this state has so much more to offer. From quaint downtowns to festivals that bring communities together, Maryland’s small towns are perfect for those who want to experience what life is like in a quiet location. This Redfin article describes 11 charming small towns in Maryland. Each has its own unique characteristics and many reasons to call it home.
1. Easton, Maryland
Median selling price: $400,000
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Located on Maryland’s Eastern Shore, Easton is known for its history, arts scene, and scenic beauty. Every November in town Waterfowl Festival. The event celebrates the region’s hunting and conservation heritage with art exhibits, dog trials and delicious local cuisine. Easton is also home to the Avalon Theater, a restored venue that hosts concerts and events year-round with national and local performers. With the River Avon nearby, locals enjoy kayaking, sailing, and spending sunny afternoons relaxing by the water.
2. Elkton, Maryland
Median selling price: $342,000
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Elkton has a unique history as the “marriage capital” of the early 20th century. This is because couples travel here to get married without any waiting time. Today, the town honors its heritage with historic sites such as Elkton Town Hall, once a popular wedding venue. The nearby Elk River offers plenty of outdoor fun, and locals enjoy boating, fishing, and picnicking by the water at Elk Neck State Park.
3. Chestertown, Maryland
Median selling price: $412,000
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Located on the Chester River, Chestertown is a picturesque town with a strong colonial history. Every Memorial Day weekend, the town comes alive with the Chestertown Tea Party Festival. The festival includes re-enactments of colonial-era protests against British taxation, with parades, boat races, and craft markets. Stroll through the historic center and explore well-preserved 18th-century houses, quaint shops, and several art galleries. The Chester River is a favorite with locals for sailing, paddleboarding, sunset cruises, and of course, fishing.
4. La Plata, Maryland
Median selling price: $420,500
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La Plata is a quiet town in southern Maryland. Every April, locals gather for the Celebrate La Plata Festival to enjoy live entertainment, crafts, and a glimpse into the town’s past. The town’s heritage is on display at the La Plata Station Museum, where you can learn about its history as a major railway stop. La Plata is also known for its scenic trails and parks, such as Tillman Lake, where people enjoy hiking, fishing, and picnicking on the weekends.
5. Denton, Maryland
Median selling price: $344,000
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Denton is located on the Choptank River on Maryland’s east coast. The town holds annual events. caroline summerfestlive music, street performers, fireworks and more. Nature lovers will enjoy kayaking along the Choptank River or exploring Martinac State Park, a tranquil spot for camping, hiking, and fishing. Downtown Denton is home to a variety of locally owned shops and cafes, including Market Street Public House, known for its friendly atmosphere and pub food.
6. Leonardtown, Maryland
Median selling price: $430,000
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The square in Leonardtown, the county seat of St. Mary’s County, is the center of local events. Popular events include the annual Earth Day Celebration and Taste of St. Mary’s Food Festival. Leonardtown Wharf Park is a local favorite for its beautiful waterfront views and kayaking and paddleboarding on Breton Bay. The town also has a great art scene, with galleries and studios showcasing local talent, especially on First Fridays, when shops and restaurants stay open until late.
7. Princess Anne, MD
Median selling price: $235,000
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Princess Anne’s downtown district features beautifully preserved 18th and 19th century buildings, including the iconic Teakle Mansion, which offers tours and seasonal events. Locals celebrate their heritage each year with events such as the Somerset County Fair, which showcases local agriculture and crafts. Residents enjoy relaxing at Jane’s Island State Park, a short drive away, where fishing, boating, and camping are popular pastimes.
8. Berlin, Maryland
Median selling price: $351,000
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Located just minutes from Ocean City, Berlin is a small town with a reputation for unique events and artistic flair. Named “coolest small town in america” In 2014, Berlin lives up to its name, with a vibrant downtown filled with art galleries, boutique shops, and beloved local eateries like Blacksmith Bar & Restaurant. Additionally, movie buffs will appreciate that Berlin was the filming location for the film. runaway bride and Tuck Everlasting.
9. Pocomoke City, Maryland
Median selling price: $235,000
Homes for sale in Pocomoke City | Apartments for rent in Pocomoke City
Known as “The Friendliest Town on the East Coast,” Pocomoke City is known for its friendly atmosphere. The Delmarva Discovery Museum is popular with visitors for its interactive aquarium featuring local wildlife, as well as exhibits that introduce the region’s ecosystem and history. Pocomoke River State Park offers plenty of outdoor fun, including beautiful trails, kayaking, fishing, and more. The downtown area is home to the Marva Theater, a beautifully restored Art Deco venue that hosts live performances and community events.
10. Manchester, Maryland
Median selling price: $517,500
Homes for sale in Manchester | Apartments for rent in Manchester
Manchester is located in northern Carroll County. Each summer, the town celebrates its German heritage with the Manchester Volunteer Fire Department Carnival, featuring rides, live music and homemade food. Manchester is also known for its scenic countryside, with rolling hills and family farms. With its close-knit community and proximity to both Baltimore and Gettysburg, Manchester has the perfect balance of country living and easy access to city amenities.
11. Hampstead, Maryland
Median selling price: $407,500
Homes for sale in Hampstead | Apartments for rent in Hampstead
One of Hampstead’s most popular events is the Hampstead Day Festival, held each spring and featuring local stalls, food trucks and live music. For history buffs, Hampstead Stationa small museum exhibiting the town’s railway history. Residents enjoy outdoor activities at Panther Park, which has walking trails, sports fields, and a playground perfect for group outings.
Methodology: Median home sales price and average monthly rent data are Redfin data center.