Our community takes pride in its local history.

Middletown, Maryland originated in 1767, boasting history older than our nation’s founding. Andrew Jackson, the nation’s seventh president, described the valley as “one of the most favored and delightful spots on earth.”

Located along Maryland’s Historic National Road, our main street made its mark as a bustling commercial center in the 19th century. Middletown’s main street felt the effects of the Revolutionary and Civil Wars firsthand, as churches and homes were transformed into headquarters and hospitals.

Our history helps tell our nation’s history and shaped our region’s personality. Though growth continues to be a part of our story, we retain our historic charm in the present day.

Middletown Heritage Gallery

Located inside of Town Hall at 31 West Main Street visitors will find historic artifacts and photos galore, engaging, and interactive exhibits, and rotating exhibits on the history of Middletown.

Middletown Heritage Park

Located across from Town Hall at 31 West Main Street is the Town’s Heritage Park. It is a place to gather, sit, relax in front of our historically inspired fountain, and learn about our history.

The Middletown Valley Historical Society

Website: https://mvhistoricalsociety.weebly.com/

The Middletown Valley Historical Society interprets the early history of the Valley in the Old Stone House at 305 West Main Street, Middletown, MD 21769. Year-round events, lectures and tours are dedicated to the valley’s special place in America’s past.

Middletown War Memorial 

Website: Middletown War Memorial

The World War II Memorial was erected and dedicated in 1947 to honor all local war veterans who served in that war. In 1999, a joint effort between Amvets Post 9 and the Town of Middletown led to the restoration of the plaques and refurbishment of the grounds of that memorial. In 2012, seven flag poles were added to recognize the five Armed Forces, POW-MIA, and the U.S. Flag.

In 2013 Amvets Post 9 and the Town of Middletown erected additional memorials on the site to honor our war veterans of all wars and conflicts in the post WWII era. Newly created monuments listing the wars: Korea, Vietnam, Operation Desert Storm/Desert Shield, Operation Iraqi Freedom, Operation Enduring Freedom, as well as, the names of those who served in each, have been installed on the site near the existing WWII Memorial. Those veterans who were killed in action have been identified for their ultimate sacrifice. The Memorial grounds have been updated to reflect the pride and reverence we have for our local veterans.

National Historic Road

170 miles of scenic byway run right through the heart of Middletown, Maryland. Our magical main street is a proud part of America’s roadway, the first federally funded highway in the United States.

The Journey Through Hallowed Ground

Website: https://www.hallowedground.org/

The Journey Through Hallowed Ground stretches along US 15 from Gettysburg, Pennsylvania to Charlottesville, Virginia. A nationally recognized area, this designated region is home to prominent historical events and spaces. Middletown is part of this journey, inviting residents and visitors to explore our piece of pivotal ground.

Heart of the Civil War Heritage Area

Website: http://www.heartofthecivilwar.org/

Middletown’s presence can be found at the Heart of the Civil War Heritage Area. This organization emphasizes places rich in history, spanning portions of Carroll, Frederick and Washington Counties. The organization serves as a resource guiding visitors to significant historical sites within the area. Visit the Heart of the Civil War Heritage Area to find out where Middletown fits into the war’s tumultuous history.



There’s 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.

Richland Golf Course

Truly a playground for all, Richland 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.   

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