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Inspired Itineraries for Middletown, Maryland

Inspired Itineraries for Middletown, Maryland

Middletown, Maryland

Embark on a journey to Middletown, Maryland, a hidden gem in the scenic Frederick County. Despite its close proximity to bustling cities like Baltimore and Washington, D.C., Middletown is a charming step back in time. Founded in 1767, this town has a rich history, having witnessed the footsteps of Revolutionary and Civil War soldiers, as well as countless travelers on their westward journey. Begin your adventure at the Main Street Middletown Welcome Center, where friendly volunteers can help plan your exploration. Eager to explore on your own? Here are three itineraries for Middletown, Maryland:

Main Street Middletown
Photo Credit: Main Street Middletown

Family Fun

Middletown is a great place for families! Don’t miss investigating the Ice Cream Trail, where you can indulge in delicious scoops on the wraparound porch at More Ice Cream, check out LDS, a local store with the oldest Hershey’s license in the United States, or visit nearby farms like MooCow Creamery and South Mountain Creamery for fresh treats. MooCow Creamery has worked extensively with their herd to weed out the proteins that make dairy products difficult for some people to digest. Plan ahead and make a reservation at South Mountain Creamery to help feed the farm’s baby cows. Peering into those big brown eyes, holding a bottle of milk, and feeling the scratchy tongue of an eager calf is something everyone needs to experience at least once in their life!

Photo Credit: South Mountain Creamery

For a taste of farm life beyond ice cream, explore Fox Haven Farm, an herbal farm, ecological retreat, learning center, and wildlife sanctuary offering fun classes like Honey Tastings, Plant Friends and Foes, as well as a Junior Herbalist class for 3-6 year olds. Here in the fall? Check out the fun activities at Jumbo’s Pumpkin Patch and enjoy their breathtaking views of the valley.

Don’t miss out on family-friendly events like Vintage Vehicles in the Valley, inspired by all of the old cars that have traveled through Middletown on the National Road (dubbed the road that settled the West).  This event brings in a multitude of beautiful old cars, tractors, fire trucks, and inventive hot-rods.

Photo Credit: Becky Axilbund/Main Street Middletown, MD Inc.

Activities surrounding the event encourage children to investigate the different types of cars, ask questions, and listen to the old-timey-horns. Little ones can test their driving skills on a Tricycle Trek with a chance to bring home a new tricycle!

Girls’ Getaway

Gather your girlfriends for a memorable weekend in Middletown. Kickstart your day with brunch at Tapia’s on Main, followed by a leisurely stroll past lovely Victorian homes on Main Street for boutique shopping at Hello Gorgeous Boutique and antiques at Wren’s Nest.

Photo Credit: Valley Homemade and Homegrown Farm in Middletown, MD

Make a stop at Gladhill Furniture for fine American crafts before arranging a flower-picking trip at Valley Homemade and Homegrown Farm. Round off your day with wine tasting at Orchid Cellar Meadery & Winery and dinner at The Main Cup or Fratelli’s.

Photo Credit: Orchid Cellar Meadery and Winery in Middletown, MD

Guys’ Retreat

For a day out with the boys, fuel up at Dempsey’s Grille before hitting the nearby Appalachian Trailhead for a rugged adventure. Choose between hiking to the historic Washington Monument or exploring the battlefields of South Mountain.

Photo Credit: The Main Cup in Middletown, MD

Cool off with brews and burgers at The Main Cup, then delve into local history at the Moran Foundation Museum, learning about the renowned bladesmith William Moran and his legacy of Damascus Steel. Fun fact: Bill Moran knives are found in the collections of celebrities such as Sylvester Stallone and King Charles!

Whether you’re traveling solo, with family, or with friends, Middletown promises a rejuvenating getaway filled with small-town charm, boutique shopping, and the bounties of the valley.


This article is sponsored by Main Street Middletown, MD Inc., a nonprofit organization dedicated to enhancing the economic vitality of the historic downtown business district. Main Street Middletown strives to bring citizens, businesses, and local government together to revitalize, preserve, promote, and support the historic downtown area.


Feature Photo Credit: Tapia’s on Main in Middletown, MD.

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