A tiny little town located on the Chesapeake and Delaware Canal, Chesapeake is an idyllic little section of Maryland filled with history and charm. The town lies right on the edge of the waterfront, and is bordered by trees and fields. These turn a lush green or a beautifully burnished bronze and orange according to the season and fill the town with color and warmth. Chesapeake itself is largely unspoiled, having retained an incredible proportion of its 19th-century buildings and houses which have been converted into inns and restaurants. The local museum is perfect for experiencing the town’s heritage and culture.
Voted American’s Coolest Small Town in 2014 by Budget Travel, Berlin is one of Maryland’s most charming and vibrant towns. Famous for depicting the fictional town of Hale in the 1999 film Runaway Bride, Berlin is just as quaint in reality as it is on the screen. The entire downtown area is a National Register Historic District, with numerous antique-looking buildings and traditional houses dating from the Federal, Victorian and early 20th-century periods. They are interspersed with sycamores, poplars and bountiful flowers, lending the area a beautiful and distinctive aesthetic.
Founded in 1792 by George and William Boone, cousins of Daniel Boone, Boonsboro is an important center for Colonial and Civil War history in the area, and is filled with historical culture. The town has six sites on the National Register of Historic Places, including the whole of the center around Main Street, and Bowman House, a gorgeous log house typical of 19th-century architecture. Boonsboro’s local surroundings are equally beautiful, with the South Mountain rising in the distance. The Antietam National Battlefield nearby provides a sombre yet striking landscape.
Located on the Chester River, Chestertown is an attractive town that is fiercely proud of it maritime heritage. The port is still in operation, with numerous sailing ships and boats coming and going throughout the day, creating a lively atmosphere. The river also features the Schooner Sultana, a beautiful replica of an 18th-century British Navy ship, which is based in the town and lends the port an impressive historical edge. The rest of Chestertown too has an incredible history, with buildings dating back to the town’s Colonial heritage, and numerous museums and galleries exploring the town’s rich past and culture.
Termed locally as ‘Where the South Begins’, Cumberland became a major player in the Civil War and its aftermath thanks to its strategic location. The town has retained much of its historic vibe from this period, with the downtown area featuring numerous beautiful historic buildings built around this period. Some of the town’s most striking architecture is found in the Washington Street Historic District. It is filled with numerous attractive public buildings and some of the state’s best preserved examples of Gothic Revival architecture. The town’s surroundings are equally as beautiful, with the Appalachian mountains rising in the distance.
Founded in 1772, Ellicott City is one of the most historic towns in the state. The town is home to the oldest surviving railway station in the country. In being made from blocks of locally quarried granite and having a gabled roof, the station exudes an old world charm, and is now used as a museum. The entire main historic district is listed on the National Register of Historic Places, and has more than 200 18th- and 19th-century buildings. There is also the largely unspoiled Main Street, which is home to numerous local shops and picturesque houses.
One of the state’s largest towns, Frederick is the ideal blend of historic and contemporary, with something remarkable to be found around every corner. The historic downtown area is notable for the ‘clustered spires’ of its numerous historic churches, which dominate the skyline and lend the area its character. Meanwhile, the two Civil War battlefields and National Museum of Civil War Medicine make this town a must-visit for any history buff. For those searching for more natural beauty, head to one of the town’s peaceful parks for an abundance of unspoiled meadows and creeks.
Known as the ‘pearl of the Chesapeake’, Rock Hall is a quaint seashore town with a thriving fishing and boating community. The harbor is filled with crab and oyster boats which leave the town every morning, returning with heaving baskets of shellfish for the town’s fresh seafood restaurants. The main town is equally lovely, with two large 18th-century mansions on the National Register of Historic Places, three museums which discuss the town’s local heritage and the maritime industry, and many picturesque board houses. The town is particularly stunning at sunset, when the warm light envelops the town and harbor in an intense glow.
The motto of St Michaels is ‘Historic Charm, Nautical Adventure, Romantic Spaces’, and this small town delivers on its promise. The downtown area is lined with quaint, old-fashioned houses, boutiques and restaurants, while the harbor is a perfect spot for all sea lovers to stroll and relax while taking in the beautiful views across the boats to the ocean. All three of the motto’s promises are rolled in the historic lighthouse, the Hooper Straight Light. This is one of only four Chesapeake Bay lighthouses built in the iconic screw-pile design, and remains one of St Michaels’ best attractions.
Located on the edges of two state parks, Thurmont is ideally placed in terms of abundant natural beauty, and is locally known as the ‘gateway to the mountains’. Cunningham Falls State Park is home to the largest cascading waterfall in Maryland, and is a site of awe-inspiring beauty. Additionally, the Catoctin Mountain Park features the edge of the Appalachian mountains, hardwood forests and winding streams just a stone’s throw from Thurmont. The main town is quaint, with charming red brick buildings and local independent shops aplenty. It also plays host to the Catoctin Colorfest, a yearly arts and crafts festival.