If you’re considering relocating to Maryland, you might immediately think of bustling cities like Baltimore or Frederick. However, Maryland has a lot more to offer, especially in its charming small towns. These towns are perfect for those looking to experience a quieter and more community-focused way of life. In this article from Redfin, we’ll explore 11 delightful small towns in Maryland, each with its own unique character and plenty of reasons to make it your home.
1. Easton, MD
Median Sale 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, arts scene, and scenic beauty. The town hosts the annual Waterfowl Festival in November, celebrating the region’s hunting and conservation heritage with art exhibits, dog trials, and local food. Easton also boasts the Avalon Theatre, a restored venue that hosts various concerts and events. With the Tred Avon River nearby, residents can enjoy activities like kayaking, sailing, and relaxing by the water.
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” in the early 20th century, where couples could get married without waiting periods. The town honors this legacy with historical sites like the Elkton Municipal Building. The Elk River offers plenty of outdoor recreation opportunities, including boating, fishing, and picnicking at Elk Neck State Park.
3. Chestertown, MD
Median Sale Price: $412,000
Homes for sale in Chestertown | Apartments for rent in Chestertown
Situated along the Chester River, Chestertown is a picturesque town with a rich colonial history. The annual Chestertown Tea Party Festival celebrates the town’s colonial protest against British taxation with a parade, boat race, and craft market. Residents can explore historic homes, shops, and art galleries in the charming downtown area. The Chester River offers opportunities for sailing, paddleboarding, and 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 peaceful town in Southern Maryland known for its Celebrate La Plata festival held every April. The town’s heritage is showcased at the La Plata Train Station Museum, highlighting its history as a key rail stop. Nature enthusiasts can enjoy Tilghman Lake for hiking, fishing, and picnicking.
5. Denton, MD
Median Sale Price: $344,000
Homes for sale in Denton | Apartments for rent in Denton
Located along the Choptank River, Denton hosts the annual Caroline Summerfest with live music and street performers. Outdoor enthusiasts can kayak on the river or explore Martinak State Park for camping, hiking, and fishing. The downtown area offers a variety of locally owned shops and cafes.
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 hosts community events like the Earth Day celebration and Taste of St. Mary’s food festival. Leonardtown Wharf Park offers scenic waterfront views and recreational activities like kayaking and paddleboarding. The town’s arts scene shines during First Fridays with galleries and studios showcasing local talent.
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 features well-preserved historic buildings, including the iconic Teackle Mansion. The town celebrates its heritage with events like the Somerset County Fair. Residents enjoy outdoor activities at Janes Island State Park.
8. Berlin, MD
Median Sale Price: $351,000
Homes for sale in Berlin | Apartments for rent in Berlin
Just minutes from Ocean City, Berlin was named “America’s Coolest Small Town” in 2014. The downtown area is filled with art galleries, boutique shops, and eateries like the Blacksmith Bar & Restaurant. Berlin has a vibrant arts scene and served as a filming location for movies like 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
Dubbed the “Friendliest Town on the Eastern Shore,” Pocomoke City offers a welcoming atmosphere. Visitors can explore the Delmarva Discovery Museum and enjoy outdoor activities at Pocomoke River State Park. The Mar-Va Theater hosts live performances and community events.
10. Manchester, MD
Median Sale Price: $517,500
Homes for sale in Manchester | Apartments for rent in Manchester
Located in Carroll County, Manchester celebrates its German heritage with the Manchester Volunteer Fire Department Carnival. The town’s countryside offers rolling hills and family-owned farms. With a close-knit community and easy access to urban amenities, Manchester provides a perfect balance of rural living and urban convenience.
11. Hampstead, MD
Median Sale Price: $407,500
Homes for sale in Hampstead | Apartments for rent in Hampstead
Hampstead’s beloved Hampstead Day Festival features local vendors, food trucks, and live music. History enthusiasts can visit the Hampstead Train Station museum. Panther Park offers outdoor activities like walking trails, sports fields, and playgrounds.
Methodology: The median home sale price and average monthly rental data are sourced from the Redfin Data Center.