If you’re considering relocating to Maryland, bustling cities like Baltimore or Frederick may immediately come to mind. However, Maryland has a lot more to offer. From charming downtowns to community festivals, the small towns of Maryland provide a unique experience of the state’s quieter side. In this Redfin blog post, we’ll explore 11 delightful small towns in Maryland, each with its own distinct 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
Easton, situated on Maryland’s Eastern Shore, is renowned for its history, arts scene, and picturesque charm. The town hosts the annual Waterfowl Festival every November, a celebration of the region’s hunting and conservation heritage with art displays, dog trials, and delicious local cuisine. With the Tred Avon River nearby, residents can enjoy activities like kayaking, sailing, or simply relaxing by the water on sunny days.
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 would come to get married without waiting periods. Today, the town commemorates this legacy with historical sites like the Elkton Municipal Building. The nearby Elk River offers plenty of outdoor activities, with boating, fishing, and waterfront picnics at Elk Neck State Park being popular among locals.
3. Chestertown, MD
Median Sale Price: $412,000
Homes for sale in Chestertown | Apartments for rent in Chestertown
Chestertown, located along the Chester River, is a picturesque town with a rich colonial history. The annual Chestertown Tea Party Festival on Memorial Day weekend brings the town to life with a reenactment of its colonial protest against British taxation. The town’s historic district features well-preserved 18th-century homes, charming shops, and art galleries. Residents enjoy various activities on the Chester River, such as 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, a serene town in Southern Maryland, hosts the annual Celebrate La Plata festival every April, featuring live entertainment and a glimpse into the town’s history. The La Plata Train Station Museum showcases the town’s railroad past. Scenic trails and parks like Tilghman Lake offer opportunities for hiking, fishing, and picnicking.
5. Denton, MD
Median Sale Price: $344,000
Homes for sale in Denton | Apartments for rent in Denton
Denton, situated along the Choptank River on Maryland’s Eastern Shore, hosts the annual Caroline Summerfest, a vibrant event with live music, street performers, and fireworks. Nature lovers can enjoy kayaking on the Choptank River or exploring Martinak State Park for camping, hiking, and fishing. Downtown Denton offers a range of locally owned shops and cafes, including the Market Street Public House known for its friendly ambiance 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 focal point for community events. The town hosts popular events like the annual Earth Day celebration and Taste of St. Mary’s food festival. Leonardtown Wharf Park offers scenic waterfront views and activities like kayaking and paddleboarding on Breton Bay. The town’s arts scene thrives with galleries and studios showcasing local talent, especially during First Fridays when shops and restaurants extend their hours.
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 boasts well-preserved 18th- and 19th-century buildings, including the iconic Teackle Mansion with tours and seasonal events. The town celebrates its heritage with events like the Somerset County Fair, highlighting local agriculture and crafts. Janes Island State Park offers residents a relaxing retreat for fishing, boating, and camping.
8. Berlin, MD
Median Sale Price: $351,000
Homes for sale in Berlin | Apartments for rent in Berlin
Berlin, just minutes from Ocean City, is a small town known for unique events and artistic charm. Voted “America’s Coolest Small Town” in 2014, Berlin’s lively downtown features art galleries, boutique shops, and popular eateries like the Blacksmith Bar & Restaurant. Movie enthusiasts will appreciate that Berlin 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
Known as the “Friendliest Town on the Eastern Shore,” Pocomoke City welcomes visitors with attractions like the Delmarva Discovery Museum showcasing the region’s ecology and history. Pocomoke River State Park offers outdoor enthusiasts opportunities for kayaking and fishing. The Mar-Va Theater in downtown 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 northern Carroll County, Manchester celebrates its German heritage with the annual Manchester Volunteer Fire Department Carnival, offering rides, music, and homemade food. The town’s scenic countryside with rolling hills and family-owned farms provides a tranquil setting. With a close-knit community and easy access to Baltimore and Gettysburg, Manchester offers a perfect blend of rural living and urban amenities.
11. Hampstead, MD
Median Sale Price: $407,500
Homes for sale in Hampstead | Apartments for rent in Hampstead
One of Hampstead’s standout events is the Hampstead Day Festival held each spring, featuring local vendors, food trucks, and live music. History enthusiasts can explore the Hampstead Train Station, a museum showcasing the town’s railroad history. Panther Park offers outdoor activities like walking trails, sports fields, and playgrounds for community gatherings.
Methodology: The median home sale price and average monthly rental data are sourced from the Redfin Data Center.