Things to do in Western Frederick County 

Between Catoctin Mountain and South Mountain lies the beautiful Middletown Valley, home to charming Main Streets, family farms, and centuries of history. A visit to western Frederick County is sure to present you with lovely views and opportunities to make life-long memories with friends and family.

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Outdoor Activities 

Hikers, rejoice! Western Frederick County is home to 40+ miles of America’s best-known hiking trail. The Appalachian Trail winds across the landscape atop South Mountain on the county’s western border. 

A view of people enjoying the Appalachian Trail hike

The trail here offers incredible views of Frederick and Washington counties, through multiple state parks, including South Mountain State Battlefield and Gathland State Park. Make it a day hike or a multi-day adventure. 

On the eastern side of the Middletown Valley is Catoctin Mountain. Much of this mountain has been preserved for use by outdoor adventurers. Beloved by mountain bikers, the Frederick Watershed (known locally simply as “The Shed,”) has dozens of miles of biking trails that also stretch into nearby Gambrill State Park. 

Mountain biking on Catoctin Mountain

Home to several races, including the Sheduro and the USA Cycling Marathon Mountain Biking National Championship, these trails aren’t for the faint of heart, but are a treasured gem for the seasoned mountain biker. 

People on their bikes at USA Cycling

Interested in a panoramic view without the hike? Check out the vistas in Gambrill State Park! Various viewing platforms provide views over the Middletown Valley and the City of Frederick. 

Hiking at Middletown Valley overlook at Gambrill State ParkThe Middletown Valley overlook at Gambrill State Park provides a majestic view with only a short walk. 



All these landscapes have played a crucial role throughout American history dating back to the years before the Revolution. European settlers began arriving in the Middletown Valley as early as the 1730s, finding rich soil for farming that remains an essential part of the region’s economy today. At the center of the Middletown Valley lies the valley’s namesake - Middletown. 

An aerial view of Main Street Middletown

This historic Maryland community dates to 1767 and has long been a stop for travelers passing through the region. Middletown became a “pike town” on the Historic National Road, a major east-west road through the Mid-Atlantic built in the earliest years of the United States. 

In 1862, the National Road brought vast armies to Middletown and western Frederick County. US and Confederate forces clashed on September 14, 1862 at the Battle of South Mountain, a victory for the US Army that set the stage for the Battle of Antietam three days later.

Battle of South Mountain - LOC

Middletown and the nearby village of Burkittsville became makeshift hospitals for thousands of wounded soldiers in the aftermath of battle.

Explore Gathland State Park and South Mountain State Battlefield to learn the full story of these battles and their impact on the local community. The National Museum of Civil War Medicine in Frederick also tells the story of how western Frederick County communities cared for the wounded during the Civil War. Discover the full story of the Civil War in the region by following numerous Civil War Trails throughout the area. 

Civil War cannon crew at Gathland State Park

In the 20th century, another transportation link connected the region. The Hagerstown and Frederick Railway was a trolley line that linked most Frederick County communities with neighboring Washington County. Operated from 1896 until the 1950s, the H&F moved passengers and goods around the region. 

Today, you can step aboard one of the surviving H&F Railway cars at the Myersville Community Library. Suburban Coach #150 rode the rails of the H&F starting in the 1920s and is now helping to educate about the golden years of public transportation in the region. 

Historic H&F Trolley at Myersville Community Library


Family Fun 

The Middletown Valley offers a wide variety of family-friendly activities to create lasting memories.

You'll find a real gem over at South Mountain Creamery, where you can indulge in the delightful experience of farm life here in Frederick County. Take a tour of the dairy farm, interact with the friendly cows, and savor fresh, creamy ice cream. South Mountain Creamery is on the Maryland Ice Cream Trail and you'll taste why! It's an educational and delicious outing for all ages.

Ice Cream from South Mountain Creamery

Nature enthusiasts will find solace at Catoctin Creek Park and Nature Center. With its tranquil trails and educational exhibits, this park is a haven for wildlife lovers. Explore the wooded trails, splash in Catoctin Creek, observe native wildlife, and discover the wonders of the local ecosystem. It's an ideal place for families to connect with nature and appreciate the beauty of Maryland's outdoors. It's a great spot to take dogs as well, one of the places that makes Frederick County a dog-friendly destination. 

Catoctin Creek Nature Center

When autumn paints the Maryland landscape with warm hues, head over to Summers Farm Fall Festival for seasonal delights. The farm transforms into a wonderland of corn mazes, pumpkin picking, hayrides, and fun activities for all ages. It's the perfect spot for families to revel in the beauty of fall and bond over shared adventures.



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Eat and Drink 

When your stomach is rumbling and you're looking for a spot to grab a bite to eat in the Middletown Valley, you've got plenty of options. 

For a cozy and charming atmosphere, look no further than The Main Cup on Main Street Middletown. This local favorite offers a diverse menu of American cuisine with dishes prepared using fresh, locally sourced ingredients. With Middletown's rich history, it shouldn't be a surprise that this restaurant has its own story. The restaurant's name comes from the building's history as local businessman C.F. Main's ice cream factory and store dating back to the early 1900s. 

View of the outside of Main Cup

Middletown is also a great place to get a taste of Italy. Two restaurants, Fratelli's and Tapia's On Main, are both serving up authentic Italian fare from pasta to pizza. 



Barbeque calling your name? Try Black Hog's Middletown location for a taste of barbeque from across the United States. Whether you are looking for St. Louis-style ribs, Carolina-style chopped pork, or Texas-style brisket, you'll find a piece of slow-cooked heaven.

Don't sleep on their wings, burgers, and salads - plenty of tasty options here. And if you happen to be traveling elsewhere in Frederick County, you can also find locations in Downtown Frederick (temporarily closed for renovations), Worman's Mill, and Urbana. 



The Middletown Valley is also home to Maryland's first meadery. Orchid Cellar Meadery can be found just north of Middletown on a farm overlooking South Mountain. This meadery specializes in crafting honey wines with a modern twist. You'll find a host of meads to try utilizing spices, chile peppers, and other ingredients that elevate Orchid Cellar's mead into works of art. Enjoy a tasting session to explore the nuances of their meads while savoring the serene vineyard views from their tasting room's stunning porch. 



Western Frederick County is a gem that beckons visitors with its diverse experiences and attractions. From thrilling outdoor adventures along South Mountain to layers of history on Main Street Middletown, this destination offers something for every traveler. Discover the rolling hills and valleys of Central Maryland, where adventure, culture, and flavors intertwine to create an unforgettable experience for all who venture here.  


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