6 Towns in Maryland that Transport You to the Past
Maryland, as the site of pivotal battles and events from the Revolutionary War, War of 1812, and Civil War, reflects the country’s fight for identity and unity. Although the centuries have passed, battlefield memorials, maritime museums, and preserved colonial districts keep Maryland’s history alive, reminding us of its lasting significance. Curious to know what life was like for Maryland’s settlers in the 17th century, or simply want to walk among ancient caves? These six towns offer the opportunity to experience a different era.
Boonsboro
Boonsboro’s history as a settlement dates back to 1792 when two brothers, George and William Boone, founded farms on the land. To learn about the last three centuries of the town’s history, visitors can explore the Boonsborough Museum of History, considered one of the region’s best private museums with an extensive Civil War collection, including artifacts from the Antietam and Gettysburg Campaigns. William Boone was buried in town, behind the Trinity Reformed United Church of Christ, which travelers can stop by as well.
To reflect on the bloodiest one-day battle in US history, a trip to the Antietam National Battlefield is interesting, featuring an eight-and-a-half-mile driving tour that passes by historical landmarks such as Bloody Lane, Dunker Church, and Burnside Bridge. For fascinating ancient rock formations, consider a visit to Crystal Grottoes Caverns, which is home to white-colored stalagmites and stalactites, natural sculptures, and other rock formations.
Chestertown
Chestertown’s rich maritime heritage dates back to its designation by the English as a Royal Port of Entry in 1706. Visitors can explore this history at the Historical Society of Kent County, which offers a self-guided phone tour for those wanting more detailed insights. The centrally located historic district will make visitors feel as though they are walking through 18th-century colonial life, filled with brick-lined streets and homes dating back to the 1700s.
One of the town’s most cherished annual events is its annual “Dickens of a Christmas” celebration, which includes historic home tours, bonfires, Victorian tea time, book talks, live entertainment, and lots of food. Travelers can also enjoy Chestertown’s weekly farmers market, taking place on Fridays, where they can buy local produce, artisan soaps, and crafts, and get a sense of the town’s culture and community spirit.
Hagerstown
Hagerstown has a colonial history that dates back to 1739 when German immigrant Jonathan Hager purchased 200 acres of land in the region. Its strategic location played a significant role during the American Civil War, leaving a lasting legacy reflected in the town’s preserved historical landmarks. Today, Hagerstown is home to about 43,500 residents and offers attractions such as the Battle of Falling Waters 1863 Foundation and the National Museum of Civil War Medicine.
Outdoor enthusiasts can also explore the Chesapeake & Ohio Canal, a historic 184.5-mile route ideal for biking and walking. After a day of exploration, visitors can relax with a cold craft beer at Hagerstown’s first full-production brewery. The tasting room and outdoor patio provide the perfect setting to unwind, with varied events such as trivia nights and live music adding to the experience.
Cambridge
Cambridge, situated along the Choptank River, is one of the state’s oldest colonies, first settled in 1684. Much of its maritime history is preserved at the Richardson Maritime Museum and Ruark Boatworks, which showcase boat building, crab catching, sailing, and fishing traditions. The renowned Harriet Tubman, a major actor in the Underground Railroad, was born nearby, whose history visitors can celebrate at the Harriet Tubman Museum in downtown Cambridge. On Race Street, a colorful mosaic mural depicts the town’s working people throughout the centuries.
For gothic architecture, visitors can stop by the Christ Episcopal Church, which has a structure from 1884, although its roots date back as far as 1694. The Cambridge House Bed and Breakfast promises a historic stay, dating back to 1847 as a sea captain’s manor and located within walking distance to many attractions and restaurants.
Easton
Walking down Easton’s downtown and historic districts, visitors can expect to be greeted by Colonial and Victorian-style buildings, historic theatres, and art galleries. The Avalon Theatre showcases the town’s architectural diversity with its beautifully restored Art Deco design. Renowned for its exceptional acoustics, the venue hosts an eclectic lineup of performances, including bluegrass, soul, and folk music.
To take home a piece of Easton with you, stop by one of the town’s art galleries, such as The Trippe Gallery, Easton Antiques & Art Gallery, or Spiralis Gallery. To learn about Talbot County, visitors can spend an afternoon at the Talbot Historical Society, which showcases historic homes, gardens, and archives from Easton’s earlier periods. The Academy Art Museum offers an impressive collection, featuring works by artists spanning from the 17th century to contemporary figures.
Saint Michaels
Saint Michaels has been an incorporated town in Maryland since 1804 and is recognized for its role during the War of 1812, where the Battle of Saint Michaels occurred. To learn more about this wartime history as well as history related to historical figure Frederick Douglass, African American history in town, and life in the St. Michaels area in the 17th century, visitors can explore the Saint Michaels museum in St. Mary’s Square. Strolling through town, a variety of prominent historical landmarks will stick out, including the Colonel Joseph Kemp House, the Dr. Dodson House, Navy Point, and Honeymoon Bridge.
The Miles River nearby is a popular place for water activities, including kayaking, sailing, or a river cruise. To immerse themselves even further in Saint Michael’s history, travelers who will be spending the weekend can stay at The Oaks Waterfront Hotel, located on a cove off of the Chesapeake Bay on a piece of property that dates all the way back to 1680.
Final Thoughts
Maryland’s rich history endures, thanks to the efforts of historical societies, local governments, and the residents of its small towns. Visitors can explore the remnants of early settlements, historic battlefields, and key sites of social movements, bringing the past vividly to life. For those who love stepping into history, these six towns offer an experience that feels like traveling back in time.
