View historical destinations, outdoor attractions WHERE CHARM AND HISTORY MEET Explore main street middle town dining Visit one of our various restaurants for breakfast, lunch, or dinner FRESH AMERICAN FARE restaurants Delightful Family Fun VINTAGE VEHICLES IN THE VALLEY Learn More

CHARMING, PEACEFUL, AND WELCOMING

Main Street Middletown is where breathtaking views and historic landmarks greet you as you make your way down the mountain to fresh American fare, just churned ice cream, one of a kind shops, wineries and one of Maryland’s only meaderies. Beyond offering live entertainment, fine art, shopping and dining Main Street Middletown offers events for your family’s next adventure and is located just miles from the Appalachian Trail head. Whether you are seeking a relaxing day surrounded by spectacular scenery, a walk in the footsteps of George Washington, or for a farm-fresh dining experience, Main Street Middletown welcomes you to the valley.

ENRICHING THE LIVES OF OUR SMALL BUSINESSES

For a small town, we offer more than graceful historic buildings! We offer a variety of delicious restaurants to tempt and treat, from comfort food to farm-to-table freshness, but be sure to save room for dessert! Our friendly services offer incredible and convenient options for residents, employees and visitors alike – state of the art salons, beautiful spas, fitness studios and more – all within our walkable downtown. Many of our businesses have dedicated generations to their professions. Our retail stores offer tailored shopping experiences and each customer is treated like family.

WHAT'S NEW

WHAT'S NEW

See what’s new on the blog.

RESOURCES

RESOURCES

Opportunities for Main Street businesses.

BUSINESS DIRECTORY

BUSINESS DIRECTORY

Find all of our great businesses.

AVAILABLE PROPERTIES

AVAILABLE PROPERTIES

Looking to purchase a property in town?

MIDDLETOWN

MIDDLETOWN

Find out what makes downtown special.

SUPPORT
MAIN STREET
MIDDLETOWN

Main Street Middletown works to enhance the quality of life, promote the economic vitality and preserve the historic character of the historic downtown community. As a designated National Main Street community, our volunteer committees work to develop and carry out vital initiatives geared towards supporting Main Street businesses, employees and residents alike. Main Street Middletown hosts an exciting series of events and is committed to continuing to strengthen downtown Middletown. As a 501(c)3 nonprofit organization Main Street Middletown relies on you and the generous support of the community it serves.