Established around 1800, Waynesboro, Pennsylvania, is halfway between Hagerstown, Maryland and Chambersburg, Pennsylvania. A trip to Waynesboro is a delightful skip back through time into a historic downtown that once claimed more millionaires than any other town east of the Mississippi. Industrialization came and went, taking a toll on its popularity, but in the last 15 years or so, it’s become the undiscovered gem along the Mason-Dixon and home to nearly 11,000 residents. Homes in and around Waynesboro reflect its progress and history in a nice mix of heritage homes, bungalows and cottages, newer residences, and farms.

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greencastle pa photo

Greencastle, Pennsylvania, is a small, historic borough in south-central Pennsylvania. Its vibrant downtown has unique shops and restaurants, and hosts an annual Craft Beer & Wine Festival as well as a Seasonal Marketplace twice a year. Every three years, residents hold “Old Home Week,” a municipal reunion, in which residents and former residents celebrate the town’s history and heritage. The tradition dates back to 1902 when it was called the “Old Boys’ Reunion.” Greencastle was settled by Scots-Irish immigrants who thought the area looked so much like home back in Ireland that they stopped and built their lives here. It truly is a place to live, work, and play. If small town life appeals to you, Greencastle should be on your list.



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smithsburg md photo

Smithsburg, Maryland, came to life in the 19th century and is relatively a newbie among towns in our area, retaining both the charm of its mid-19th—early 20th century residences, while embracing road improvements and more suburban lifestyles. The town recently hired 54-years young Debra—you guessed it—Smith as their very first town manager who says Smithsburg citizens have been so welcoming. She serves alongside Mayor Mildred “Mickey” Myers to make Smithsburg a great little place to call home.

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Brunswick MD photo

Railroad town Brunswick, Maryland touts itself as a “Big Town, Small City” and is home to more than 6,000 residents. Situated by the Potomac River along the B&O Railroad, the MARC Train offers rail commuter service to points south including Rockville, Bethesda and Washington, D.C. This Frederick County town has hiking and biking opportunities along the C&O Canal and unique businesses like Beans in the Belfry, a historic church converted to a café and meeting place, and Smoketown Brewing Station, an old fire station converted to a craft brewery. The Brunswick Heritage Museum, adjacent to the C&O Canal Visitor Center, houses one of the largest model train layouts on the East Coast. Brunswick has a delightful mix of vintage homes, as well as modern estates and townhomes. It’s perfect for professionals desiring an upbeat community! Point of Rocks, Maryland; Leesburg, Virginia; and Harpers Ferry, West Virginia are all just a short drive.


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williamsport md photo

Locally known as “Waymz-port,” Williamsport, Maryland, says that “fun is our tradition” defined as music, dance, sports, and recreation activities in this popular waterfront town along the Potomac River. Just over 2,100 residents strong, this unique town hosts historic locations as well as shops, galleries, and eateries. You can also pick up the C&O Canal tow path here for a hike or bike through the Maryland countryside. Single-family homes here anchor families close to Hagerstown, Maryland, and are also convenient to Martinsburg, West Virginia.



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Emmitsburg MD photo

Just south of the Mason-Dixon Line, in Frederick County, sits the small town of Emmitsburg, Maryland. Home to just over 3,000 households, it’s a growing community with new construction that attracts families who long for quiet countryside but still want easy access to Frederick and Baltimore. The National Shrine Grotto of our Lady of Lourdes is located in Emmitsburg on the campus of Mount St. Mary’s University. Just up Route 15 is the Basilica and National Shrine of St. Elizabeth Ann Seton, the first natural born U.S. citizen to be canonized as a saint. Next door to the Seton Shrine is the National Emergency Training Center, which includes the National Fire Academy. The National Fallen Firefighters Memorial is located on the grounds as well as the 9/11 Memorial – To Lift a Nation.  This small town community offers lots of local shopping and dining as well as quiet corners for reflection.


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sharpsburg md photo

The small, historic town of Sharpsburg, Maryland, in southern Washington County, is home to just over 700 residents. Many homes on Main Street in Sharpsburg look just as they did in 1862 when the Battle of Antietam was fought. Today Antietam National Battlefield is considered one of the most well preserved Civil War battlefields and is a scenic place to walk, hike, bike, explore and learn about history. The town’s longest-standing tradition is its Memorial Day parade, a glimpse of small-town America with marching bands, school groups, athletic teams, reenactors, beauty queens and more. The Chesapeake and Ohio (C&O) Canal is also accessible from several nearby points, offering additional opportunities to enjoy the outdoors. Just remember to end your day outside with a trip to Nutter’s Ice Cream, just off the town square!

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Frederick MD photo

Frederick is the second largest incorporated city in the state of Maryland, next to Baltimore. This great American Main Street community has everything you’d expect from an urban setting, along with a rich history. Carroll Creek Park winds through the middle of walkable, dog-friendly downtown Frederick, creating residential and economic expansion, while preserving the unique “Clustered Spires” and historic buildings. Frederick boasts great restaurants, unique shops and boutiques, art galleries, theaters and museums as well as craft breweries and distilleries. Businesses of all sizes and types are attracted to the area, making it a good place for employment opportunities. Top-rated schools, health care and a vibrant arts community, all against the backdrop of the scenic Catoctin Mountains, make Frederick the urban epicenter for sophistication.

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chambersburg pa photo

Approximately 20 minutes north of the Mason-Dixon line is Chambersburg, Pennsylvania. This quintessential small town has rich agricultural roots and is home to many Amish and Mennonite residents who farm the land today. The town was completely rebuilt after being burned in 1864 by the Confederate army during the American Civil War. Today it is a large, diverse community with an active Downtown Business Council, working to improve and promote downtown Chambersburg with festivals, special events and promotions throughout the year. Surrounding colleges and universities offer a plethora of cultural events. While the town retains its historical feel, large farms pepper the countryside along with farm stands and craft shops.


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Middletown MD photo

Historic Middletown, Maryland, is another Frederick County Main Street Community nestled in the scenic valley between Braddock and South Mountains. Historic Victorian homes grace the main thoroughfare, the National Road. It’s no surprise that George Washington passed through this valley and called it one of the most beautiful places he’d ever seen. Who wouldn’t want to find themselves at home in this peaceful rural setting, just a short drive from Frederick? The area has a rich agricultural history that is still apparent today, but with a modern twist. Just at the edge of town, South Mountain Creamery offers farm fresh ice cream and the opportunity to bottle feed baby calves year round.  Jumbo’s Pumpkin Patch is a popular fall destination for family fun with hay rides, corn mazes and of course, pumpking picking. Orchid Cellar Meadery and Winery offers a brand new tasting room and award-winning honey wines as well as red and white varietals. Middletown has something for everyone!

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