Why not expand your visit to more than just Main Street Middletown?  There is a whole valley waiting to be discovered!  Add one of these close-by destinations for a full day of family fun, recreation, and learning.

Antietam National Battlefield

This nearby National Battlefield commemorates the bloodiest one-day battle in American history. The ultimate regional stop for history lovers, Antietam’s legacy lives on as more than just lives lost. This battle directly led to President Abraham Lincoln’s issuance of the preliminary Emancipation Proclamation, transforming the fight into a battle for human freedom. 

Appalachian Trail

Middletown residents are fortunate to have access to the Appalachian Trail just outside of town. The southern part of the trail leads to Reno monument and the northern path leads its visitors to Annapolis Rocks in Myersville, Maryland. No matter which way you choose, fabulous views are in your future.

Bill van Gilder Pottery

Tap into creativity in our backyard. Bill van Gilder’s Maryland Gallery is host to a collection of artists’ work including everything from photographic art to woodwork. Ceramic enthusiasts can learn from one of the best, as Bill van Gilder has lead workshops nationally and internationally pertaining to pottery forming, decorating, and firing techniques, as well as kiln building. Guests are welcome to visit and tour the art space when it’s open each weekend or during any of its special events.

Dahlgren Chapel

Sitting atop South Mountain between Middletown and Boonsboro, this historic chapel full of local history, is now making its mark on modern life. Constructed by the influential Dahlgren family in the 1880s, the chapel is open for weddings and private services.

Distillery Lane Ciderworks (DLC)

Visit these apple-picking neighbors. This family owned and operated 95-acre farm specializes in providing the region with award-winning fresh apple cider and hard apple cider beverages.  Offering self-guided tours, group tours and tastings is regular business for DLC. Guests are welcome to partake in cider making classes in the spring and summer.

Fox’s Gap

Fox’s Gap is a beautiful hallowed valley that commemorates where General Reno was killed during the Civil War. Reno’s soldiers commemorated his death by erecting the monument in 1889.

Gambrill State Park

Plan a picnic or plan your escape. Over 16 miles of hiking, biking and horseback riding trails await any adventurer looking for a day in the mountains at Gambrill State Park.

Hollow Creek Golf Course

Truly a playground for all, Hollow Creek is a place for golfers and their families. A favorite for those who want to take on the toughest shots, this beautiful club is also host to a local family-friendly hideaway, Valley Grill Sports Bar.

Jumbo’s Pumpkin Patch

Sometimes a name says it all.  Come fall, kids of all ages can find jumbo-sized fun picking out a pumpkin, catching a seat on a hayride, paling around with ponies and partaking in the Jumbo’s petting zoo.

Maryland National Golf Club

Designed by world-renowned architect Arthur Hills and seated in the spectacular surroundings of the Middletown Valley area, this 18 hole, par 71- course offers a world-class golfing experience for players at every level. 

Monocacy National Battlefield

When the Confederate Army threatened to capture Washington D.C. during the Civil War, Union troops engaged the Confederates along the Monocacy River banks. Not far from Middletown, the Monocacy Battlefield is just another important historical landmark our region offers.

Orchid Cellar Meadery & Winery

This meadery and winery boasts an international clientele but exhibits the local charm you’d only find in the Middletown Valley. Products crafted right from our fertile valley, Orchid Cellar, a leader in boutique alcoholic beverages, adds distinct appeal to our valley.

South Mountain Battlefield

Preserving the past, this national historic place tells the story of Maryland’s first Civil War battle as Lee’s army entered its Maryland campaign and mounted resistance against an ultimately victorious Union Army.

South Mountain Creamery

Truly a one-of-a-kind experience right in Middletown, guests come to the South Mountain Creamery to meet the men, women and animals that provide delicious dairy products to loyal customers all over the region.

Surreybrooke Gardens & Nursery

Winding paths overflowing with foliage greet guests at this center for award-winning horticulture. Explore the greenhouses and take something home or simply breathe in the botanical beauty of this unique destination.

Washington Monument State Park

Come visit the first completed monument dedicated to the memory of George Washington. After hearing the news of Washington’s death, Boonsboro’s citizens constructed the 30-foot high memorial that was completed in 1827.   

Meet Us on Main Street!

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Main Street Maryland

Upcoming Events

Sat 27

Green Expo

April 27
Sat 27

Coloring the Street Chalk Art

April 27 @ 8:00 am - 5:00 pm
Sat 18

Walking Tour

May 18
Sat 25