What to see: : Explore downtown and enjoy the historic architecture, specialty shopping, galleries and a waterfront promenade. Don't forget to see what Washington College has going on while you visit. The college recently launched its "History on the Waterfront" one-hour walking tour on Fridays and Saturdays. The audio-guided tour allows participants to stroll along the historic waterfront and listen to music, re-enactments and firsthand accounts of life in the Colonial port.
What to do: : Chesapeake Farms, a 3,300-acre wildlife and agricultural research and demonstration site, includes a self-guided driving tour through the landscape where visitors can discover farm ponds, sunflower fields, rabbit fields, marsh and wetlands.
Where to stay: : The town boasts many bed and breakfasts to choose from, including the White Swan Tavern, the Great Oak Manor and the Brampton Bed and Breakfast Inn.
When to go: : Chestertown will be the hot spot from Oct. 28 to Nov. 1 for the Schooner Sultana's ninth annual Downrigging Weekend. The event marks the beginning of "downrigging" for many of the region's tall ships and traditional sailing vessels. Films, demonstrations, cocktail parties and public cruises are all offered during the extended weekend.
Information: : chestertown.com
Cumberland
Small-town charm meets mountain scenery, and what better time of the year than now to enjoy both? This destination offers the state's first Certified Heritage Area near the terminus of the Chesapeake and Ohio Canal, while the town's historic district boasts an impressive collection of mid-19th century and early-20th century architecture.
What to see: : Cumberland is the western terminus of the 184.5-mile C&O Canal Towpath, a well-kept pathway for hikers, bikers and horseback riders. It also connects to the 150-mile Great Allegheny Passage, allowing ambitious bikers to travel from Pittsburgh to Washington via both trails.
What to do: : The Western Maryland Scenic Railroad leaves the depot in Cumberland and travels through the scenic countryside to Frostburg. A short layover gives you time to enjoy lunch in Frostburg before heading back to Cumberland. This fills up quickly, so make reservations in advance.
Where to stay: : The Rocky Gap Lodge and Golf Resort sits on the shores of Lake Habeeb and is offering a three-night family package for $218 through October. If you prefer to stay within walking distance to the shops and sites of downtown, try the Cumberland Holiday Inn.
