If you’re thinking about moving to Maryland, bustling cities like Baltimore or Frederick might come to mind. 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 looking to experience what life is like in its quieter corners. In this Redfin article, we’ll discuss 11 charming small towns in Maryland, each with their own unique character and plenty of reasons to call home.
1. Easton, MD
Median Sale Price: $400,000
Homes for sale in Easton | Apartments for rent in Easton
Easton, located on Maryland’s Eastern Shore, is known for its history, arts scene, and scenic charm. Every November, the town hosts the Waterfowl Festival. An event that celebrates the region’s hunting and conservation heritage with art exhibits, dog trials, and delicious local food. Easton is also home to the Avalon Theatre, a restored venue that has national and local performers 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 Sale Price: $342,000
Homes for sale in Elkton | Apartments for rent in Elkton
Elkton has a unique history as the “Marriage Capital” during the early 20th century. This is because couples would travel here to get married without waiting periods. Today, the town honors that legacy with historical sites like the Elkton Municipal Building, which once served as the popular wedding venue. The nearby Elk River offers plenty of outdoor fun, with locals enjoying boating, fishing, and waterfront picnics at Elk Neck State Park.
3. Chestertown, MD
Median Sale Price: $412,000
Homes for sale in Chestertown | Apartments for rent in Chestertown
Chestertown, sitting along the Chester River, is a picturesque town with a strong colonial past. Every Memorial Day weekend, the town comes alive with the Chestertown Tea Party Festival. This festival includes a reenactment of its colonial protest against British taxation, complete with a parade, boat race, and craft market. 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, paddleboarding, sunset cruises, and of course, fishing.
4. La Plata, MD
Median Sale Price: $420,500
Homes for sale in La Plata | Apartments for rent in La Plata
La Plata is a quiet town in Southern Maryland. Each April, locals come together for the Celebrate La Plata festival, enjoying live entertainment, crafts, and a glimpse into the town’s past. The town’s heritage is on display at the La Plata Train Station Museum, where you can learn about its history as a key rail stop. La Plata is also known for scenic trails and parks, such as Tilghman Lake, where people spend weekends hiking, fishing, and picnicking.
5. Denton, MD
Median Sale Price: $344,000
Homes for sale in Denton | Apartments for rent in Denton
Denton is located along the Choptank River on Maryland’s Eastern Shore. The town hosts the annual Caroline Summerfest, a lively event featuring live music, street performers, and fireworks. Nature enthusiasts enjoy kayaking along the Choptank or exploring Martinak State Park, a serene spot for camping, hiking, and fishing. Downtown Denton features a variety of locally owned shops and cafes, like the Market Street Public House, known for its friendly atmosphere and pub fare.
6. Leonardtown, MD
Median Sale Price: $430,000
Homes for sale in Leonardtown | Apartments for rent in Leonardtown
As the county seat of St. Mary’s County, Leonardtown’s square is a hub for community events. Popular events including the annual Earth Day celebration and Taste of St. Mary’s food festival. Leonardtown Wharf Park is a favorite among locals with scenic waterfront views and opportunities for kayaking or paddleboarding on Breton Bay. The town also has a great arts scene, with galleries and studios showcasing local talent, especially during First Fridays, when shops and restaurants stay open late.
7. Princess Anne, MD
Median Sale Price: $235,000
Homes for sale in Princess Anne | Apartments for rent in Princess Anne
Princess Anne’s downtown district is home to beautifully preserved 18th- and 19th-century buildings, including the iconic Teackle Mansion, which offers tours and seasonal events. Each year, locals celebrate their heritage with events like the Somerset County Fair, showcasing local agriculture and crafts. Residents enjoy relaxing at the Janes Island State Park, a short drive away, where fishing, boating, and camping are favorite pastimes.
8. Berlin, MD
Median Sale Price: $351,000
Homes for sale in Berlin | Apartments for rent in Berlin
Berlin, located just minutes from Ocean City, 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 lively downtown filled with art galleries, boutique shops, and locally loved eateries like the Blacksmith Bar & Restaurant. Additionally, movie buffs will appreciate that Berlin served as the filming location for the films Runaway Bride and Tuck Everlasting.
9. Pocomoke City, MD
Median Sale Price: $235,000
Homes for sale in Pocomoke City | Apartments for rent in Pocomoke City
Known as the “Friendliest Town on the Eastern Shore,” Pocomoke City is known for its welcoming atmosphere. Visitors love the Delmarva Discovery Museum, where exhibits highlight the ecology and history of the region, along with interactive aquariums featuring local wildlife. Pocomoke River State Park offers plenty of outdoor fun, with scenic trails, kayaking, and fishing opportunities. The downtown area is home to the Mar-Va Theater, a beautifully restored art deco venue that hosts live performances and community events.
10. Manchester, MD
Median Sale Price: $517,500
Homes for sale in Manchester | Apartments for rent in Manchester
Manchester is located in the northern part of Carroll County. The town celebrates its German heritage every summer 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-owned farms adding to the landscape. With a tight-knit community and proximity to both Baltimore and Gettysburg, Manchester has the perfect balance of rural living and easy access to urban amenities.
11. Hampstead, MD
Median Sale Price: $407,500
Homes for sale in Hampstead | Apartments for rent in Hampstead
One of the Hampstead’s most beloved events is the Hampstead Day Festival, held every spring, featuring local vendors, food trucks, and live music. History buffs can explore the Hampstead Train Station, a small museum showcasing the town’s railroad past. Residents enjoy outdoor activities at Panther Park, with walking trails, sports fields, and playgrounds perfect for group outings.
Methodology: The median home sale price and average monthly rental data is from the Redfin Data Center.
