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11 Charming Small Towns in Maryland You Need to Visit

Maryland is a state brimming with diverse landscapes, rich history, and small-town charm waiting to be discovered. From the rolling hills of the countryside to the bustling waterfronts of its cities, this state offers a delightful array of experiences for visitors and locals alike. In this Redfin article, we’ll explore 11 small towns in Maryland, each offering its own unique blend of character, culture, and hospitality. Let’s get started.

Marina at Annapolis, Maryland

1. Easton, MD

Median Sale Price: $414,500

Homes for sale in Easton | Apartments for rent in Easton

The town of Easton is known for its historic downtown area, beautiful waterfront, and vibrant arts scene. Those visiting can spend their time exploring the local art galleries, boutique shops, and delicious seafood restaurants. The town also hosts several annual events and festivals, including the Waterfowl Festival and the Easton Plein Air Competition.

2. Elkton, MD

Median Sale Price: $325,00

Homes for sale in Elkton | Apartments for rent in Elkton

Elkton is a historic town with a rich colonial past. Visitors can explore the quaint downtown area, which is home to a variety of antique shops and local eateries. Outdoor enthusiasts will appreciate the town’s proximity to Elk Neck State Park, where they can go hiking, camping, and experience stunning views of the Chesapeake Bay.

3. Chestertown, MD

Median Sale Price: $385,000

Homes for sale in Chestertown | Apartments for rent in Chestertown

Chestertown is a picturesque waterfront town recognized for its cobblestone streets and 18th-century architecture. The town is home to Washington College, the tenth oldest college in the United States, and hosts a variety of cultural events and performances throughout the year. Visitors can also enjoy scenic river cruises and waterfront dining options.

fish on a boat with sunset in the back in maryland

4. La Plata, MD

Median Sale Price: $445,000

Homes for sale in La Plata | Apartments for rent in La Plata

Nestled in Southern Maryland, La Plata is known for its charming downtown filled with local shops and eateries. The town has a tight-knit community atmosphere, with regular events like the Farmers’ Market and outdoor concerts in the summer.

5. Denton, MD

Median Sale Price: $271,000

Homes for sale in Denton | Apartments for rent in Denton

Located on Maryland’s Eastern Shore, Denton boasts a rich history and a welcoming vibe. History buffs can spend the day at the Caroline County Historical Society Museum to learn about the town’s past, while outdoor enthusiasts can kayak on the Choptank River. With its small-town appeal and peaceful surroundings, Denton offers a tranquil retreat from the hustle and bustle of city life.

6. Leonardtown, MD

Median Sale Price: $558,000

Homes for sale in Leonardtown | Apartments for rent in Leonardtown

As the oldest municipality in Maryland’s Southern Maryland region, Leonardtown exudes historic charm and modern appeal. Stroll along the waterfront boardwalk and dine at local restaurants offering fresh seafood specialties. Locals enjoy a thriving arts scene, with galleries showcasing the work of local artists, making Leonardtown a vibrant and culturally rich community.

7. Princess Anne, MD

Median Sale Price: $140,000

Homes for sale in Princess Anne | Apartments for rent in Princess Anne

Princess Anne, MD is a historic small town in Maryland with a strong colonial heritage and a variety of cultural attractions. Be sure to visit the town’s historic district, which is home to beautifully preserved 18th-century architecture and a variety of local shops. The town also hosts regular events and festivals, including the Teackle Mansion Candlelight Tour and the Somerset Strawberry Festival.

8. Berlin, MD

Median Sale Price: $460,000

Homes for sale in Berlin | Apartments for rent in Berlin

Known as “America’s Coolest Small Town,” Berlin is a picturesque community with a vibrant Main Street filled with boutique shops and cozy cafes. The town also has regular events and festivals, including the Berlin Fiddler’s Convention and the Berlin Jazz and Blues Bash. With its inviting atmosphere and welcoming locals, Berlin provides the quintessential small-town experience.

house in maryland

9. Pocomoke City, MD

Median Sale Price: $165,000

Homes for sale in Pocomoke City | Apartments for rent in Pocomoke City

Situated on the scenic Pocomoke River, Pocomoke City is a hidden gem with plenty of outdoor activities to enjoy. While visiting, don’t miss the Delmarva Discovery Center, where you can learn about the region’s natural and cultural history.

10. Manchester, MD

Median Sale Price: $326,500

Homes for sale in Manchester | Apartments for rent in Manchester

Manchester is known for its beautiful parks and historic architecture. The town hosts regular events and festivals, including the Manchester Carnival and the Manchester Valley High School Fall Craft Show, providing plenty of entertainment for residents and visitors alike. Outdoor enthusiasts will appreciate the town’s proximity to Pine Valley Park, which offers hiking trails, picnic areas, and playgrounds.

11. Hampstead, MD

Median Sale Price: $362,500

Homes for sale in Hampstead | Apartments for rent in Hampstead

Hampstead is a charming small town in Maryland with a strong sense of community and a variety of cultural attractions. The town’s Main Street is lined with local shops and restaurants so there’s always something to do on the weekends. The town is rich in history, with landmarks like the Hampstead Train Station Museum, which showcases its railroad heritage.

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