When you think about moving to Maryland, bustling cities like Baltimore or Frederick may come to mind. However, this province has a lot to offer. From small towns to community festivals, Maryland’s small towns are perfect for anyone who wants to experience what life is like in its quiet corners. In this Redfin article, we’ll discuss 11 adorable small towns in Maryland, each with its own unique character and plenty of reasons to call it home.
1. Easton, MD
Median Auction Price: $400,000
Easton Real Estate | Real estate in Easton
Easton, located on Maryland’s Eastern Shore, is known for its history, art scene and natural beauty. Every November, the city holds a Water 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 hosts national and local performers for concerts and events throughout the year. With the Tred Avon River nearby, locals enjoy kayaking, sailing, or just relaxing on the water on sunny afternoons.
2. Elkton, MD
Median Auction Price: $342,000
Real Estate for Sale in Elkton | Real estate in Elkton
Elkton has a unique history as the “Wedding Capital” of the early 20th century. This is because couples used to go here to get married without any waiting times. Today, the town honors that legacy with historic sites like 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 seaside picnics at Elk Neck State Park.
3. Chestertown, MD
Median selling price: $412,000
Chestertown Real Estate | Apartments for rent in Chestertown
Chestertown, sitting along the River Chester, is a beautiful town with a colonial past. Every Memorial Day weekend, the town comes alive with the Chestertown Tea Party Festival. The festival includes a reenactment of colonial protests 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 fishing.
4. La Plata, MD
Median selling price: $420,500
Houses in La Plata | Real estate in La Plata
La Plata is a quiet town in Southern Maryland. Every April, locals gather to celebrate the La Plata festival, enjoying live entertainment, crafts, and views of the city’s past. The city’s heritage is on display at the La Plata Train Station Museum, where you can learn about its history as an important train stop. La Plata is also known for its scenic trails and parks, such as Tilghman Lake, where people spend their weekends hiking, fishing, and cleaning.
5. Denton, MD
Median Auction Price: $344,000
Homes in Denton | Real estate in Denton
Denton is located along the Choptank River on Maryland’s Eastern Shore. The town hosts the annual Caroline Summerfest, a fun event with live music, street performers, and fireworks. Nature lovers enjoy kayaking along the Choptank or exploring Martinak State Park, a tranquil area for camping, hiking and fishing. Downtown Denton has a variety of locally owned shops and cafes, such as the Market Street Public House, known for its friendly atmosphere and theatrical fare.
6. Leonardtown, MD
Median selling price: $430,000
Leonardtown Real Estate | Leonardtown real estate
As the county seat of St. Mary’s County, Leonardtown Square is the center of public events. Popular events include the annual Earth Day celebration and the St. Mary’s. Leonardtown Wharf Park is a favorite among locals with beautiful waterfront views and opportunities for kayaking or paddleboarding in Breton Bay. The town also has a great arts scene, with galleries and studios showcasing local talent, especially on First Fridays, when shops and restaurants stay open late.
7. Princess Anne, MD
Median Auction Price: $235,000
Princess Anne Real Estate | Apartments for rent in Princess Anne
The Princess Anne district is home to well-preserved 18th and 19th century buildings, including the iconic Teackle Mansion, which offers seasonal tours and events. Each year, locals celebrate their heritage with events like the Somerset County Fair, which showcases local agriculture and crafts. Residents enjoy relaxing at Janes Island State Park, a short drive away, where fishing, boating and camping are favorites.
8. Berlin, MD
Median selling price: $351,000
Real estate 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 art. 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 local favorites like Blacksmith Bar & Restaurant. Additionally, movie buffs will appreciate that Berlin has served as a filming location The Runaway Bride again Tuck Everlasting.
9. Pocomoke City, MD
Median selling price: $235,000
Real estate for sale in Pocomoke City | Apartments for rent in Pocomoke City
Known as the “Friendliest City on the Eastern Shore,” Pocomoke City is known for its welcoming spirit. Visitors love the Delmarva Discovery Museum, where exhibits highlight the region’s ecology and history, as well as interactive aquariums with 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 renovated art space that hosts live performances and community events.
10. Manchester, MD
Median selling price: $517,500
Real estate for sale in Manchester | Real estate 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, which includes rides, live music, and homemade food. Manchester is known for its picturesque countryside, with rolling hills and family-run farms adding to the scene. 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 selling price: $407,500
Houses in Hampstead | Houses in Hampstead
One of the most popular events in Hampstead is the Hampstead Day Festival, held every spring, featuring local vendors, food trucks, and live music. History buffs can explore Hampstead Railway Station, a small museum showcasing the town’s railway past. Residents enjoy outdoor activities at Panther Park, with walking trails, playgrounds, and playgrounds perfect for group outings.
How to do it: Median home sales price and median monthly rental data from Redfin Data Center.
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