11 Charming Small Towns in Maryland You Must Visit

If you think about it moving to MarylandYou may be thinking of vibrant cities like Baltimore or Frederick. However, this state has much more to offer. From quaint downtowns to festivals that bring the community together, Maryland’s small towns are perfect for anyone who wants to experience what life is like in its quieter corners. In this Redfin article, we discuss 11 charming small towns in Maryland, each with their own unique character and plenty of reasons to call home.

1. Easton, MD

Median sales price: $400,000
Homes for Sale in Easton | Apartments for rent in Easton

Located on Maryland’s Eastern Shore, Easton is known for its history, art scene, and quaint charm. Every year in November the city organizes the Waterfowl festival. An event that celebrates the region’s hunting and conservation heritage with art exhibitions, dog trials and delicious local food. Easton is also home to the Avalon Theater, a restored venue that hosts national and local artists for concerts and events throughout the year. With the Tred Avon River nearby, locals enjoy kayaking, sailing or simply relaxing by the water on sunny afternoons.

2. Elkton, MD

Median sales price: $342,000
Homes for Sale in Elkton | Apartments for rent in Elkton

Elkton has a unique history as the “marriage capital” of the early 20th century. This is because couples would travel here to get married with no waiting times. Today, the city honors that legacy with historic landmarks such as the Elkton Municipal Building, which once served as a popular wedding venue. The nearby Elk River offers plenty of outdoor fun, with locals enjoying boating, fishing and picnicking by the water at Elk Neck State Park.

3. Chestertown, MD

Median sales price: $412,000
Homes for Sale in Chestertown | Apartments for rent in Chestertown

Located on the Chester River, Chestertown is a picturesque town with a strong colonial past. Every Memorial Day weekend the city comes alive with the Chestertown Tea Party Festival. This festival includes a re-enactment of the colonial protest against British taxation, complete with a parade, boat race and craft market. While strolling through the historic district, visitors can explore well-preserved 18th-century homes, quaint shops, and several art galleries. The Chester River is a favorite among locals for sailing, paddle boarding, sunset cruises and of course fishing.

4. La Plata, MD

Median sales price: $420,500
Houses for sale in La Plata | Apartments for rent in La Plata

La Plata is a quiet town in Southern Maryland. Every April, locals gather for the Vier La Plata festival, where they enjoy live entertainment, crafts and a glimpse into the city’s past. The city’s heritage can be seen at La Plata Train Station, where you can learn about the train station’s history as an important railway stop. La Plata is also known for its scenic trails and parks, such as Tilghman Lake, where people spend the weekend hiking, fishing, and picnicking.

5. Denton, MD

Median sales price: $344,000
Homes for Sale in Denton | Apartments for rent in Denton

Denton is located along the Choptank River on the Eastern Shore of Maryland. The city organizes the annual Caroline Summer Partya lively event with live music, street performers and fireworks. Nature lovers enjoy kayaking along the Choptank or exploring Martinak State Park, a serene place for camping, hiking and fishing. Downtown Denton features a variety of local shops and cafes, such as the Market Street Public House, known for its friendly atmosphere and pub fare.

6. Leonardtown, MD

Median sales price: $430,000
Homes for Sale in Leonardtown | Apartments for rent in Leonardtown

As the county seat of St. Mary’s County, Leonardtown Square is a hub for community events. Popular events including the annual Earth Day celebration and the Taste of St. Mary’s food festival. Leonardtown Wharf Park is a favorite among locals, with scenic water views and opportunities for kayaking or paddleboarding on Breton Bay. The city also has a great arts scene, with galleries and studios showcasing local talent, especially during First Friday, when shops and restaurants stay open late.

7. Princess Anne, MD

Median sales price: $235,000
Houses for sale in Princess Anne | Apartments for rent in Princess Anne

Downtown Princess Anne is home to beautifully preserved buildings from the 18th and 19th centuries, including the iconic Teackle Mansion, which hosts tours and seasonal events. Every year, local residents celebrate their heritage with events such as the Somerset County Fair, which showcases local agriculture and crafts. Residents enjoy relaxation at Janes Island State Park, a short drive away, where fishing, boating and camping are favorite pastimes.

8. Berlin, MD

Median sales price: $351,000
Houses for sale in Berlin | Apartments for rent in Berlin

Located just minutes from Ocean City, Berlin is a small town with a reputation for unique events and artistic flair. Named “America’s Coolest Small Town” in 2014, Berlin lives up to its title with a vibrant center full of art galleries, boutiques and locally beloved eateries such as the Blacksmith Bar & Restaurant. Additionally, film buffs will appreciate that Berlin served as a filming location for the films Runaway bride And Lasting forever.

9. Pocomoke City, MD

Median sales price: $235,000
Homes for Sale in Pocomoke City | Apartments for rent in Pocomoke City

Pocomoke City is known as the “friendliest city on the East Coast” and is known for its welcoming atmosphere. Visitors love the Delmarva Discovery Museum, where exhibits highlight the region’s ecology and history, along with interactive aquariums featuring local wildlife. Pocomoke River State Park offers plenty of outdoor fun, with scenic trails, kayaking, and fishing opportunities. Downtown is the Mar-Va Theater, a beautifully restored Art Deco venue that hosts live performances and community events.

10. Manchester, MD

Median sales price: $517,500
Houses for sale in Manchester | Apartments to rent in Manchester

Manchester is located in the northern part of Carroll County. The city celebrates its German heritage every summer with the Manchester Volunteer Fire Department Carnival, featuring rides, live music and home-cooked food. Manchester is also known for its picturesque countryside, with rolling hills and family farms adding to the landscape. With a close-knit community and close proximity to both Baltimore and Gettysburg, Manchester has the perfect balance of rural living and easy access to urban amenities.

11. Hampstead, MD

Median sales price: $407,500
Houses for sale in Hampstead | Apartments to rent in Hampstead

One of the most beloved events in Hampstead is the Hampstead Day Festival, held every spring, featuring local vendors, food trucks and live music. History buffs can check out the Hampstead railway stationa small museum about the city’s railway past. Residents enjoy outdoor activities at Panther Park, with walking trails, sports fields and playgrounds perfect for group outings.

Methodology: The average home sales price and average monthly rental data comes from the Redfin Data Center.