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Chestertown overview

Chestertown is a friendly locale distinct for its historical sites and festivals, and known for its college atmosphere and shops. You'll enjoy the ample dining choices. Visitors can plan a fun excursion to Rolphs Wharf Marina and Rock Hall Harbor. Be sure stop by Wilmer Park and River Arts Chestertown while you're here. A family-friendly area, Chestertown also has something for everyone.

Where to stay in Chestertown

Whether you're planning to stay for a night or for the week, the area around Chestertown has accommodations to fit every need. Search for hotels in Chestertown with by checking our online map. Our maps display the areas and neighborhoods around all Chestertown hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Chestertown hotel deals are here with our lowest price guarantee.

How to get to Chestertown

Fly in to Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), 30.8 mi (49.6 km) from downtown Chestertown. Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) is the next closest major airport, 67.2 mi (108.1 km) away.

What to see around Chestertown

Fun activities such as boating, horseback riding, and sporting events are at hand, along with attractions such as:
  • • Rolphs Wharf Marina
  • • Rock Hall Harbor
  • • Essex Marina
  • • Freestate Gun Range
  • • Wye Landing
A top draw is the area's festivals, as well as places like:
  • • Garfield Center for the Arts at the Prince Theater
  • • Historical Society of Kent County Maryland
  • • The Mainstay
  • • Mount Harmon Plantation
  • • Cal Ripken Museum
Take some time to explore campus or the area surrounding:
  • • River Arts Chestertown
  • • Washington College
Here are some top sights to see:
  • • Wilmer Park
  • • Cassinelli Winery and Vineyards
  • • Ferry Park
  • • Tilmon's Island Winery
  • • Queenstown Harbor Golf Club

When to visit Chestertown

Wondering when's the best time to visit? Here are seasonal norms to help you plan your trip:

Seasonal temperature averages
  • January-March: 58°F day, 25°F night
  • April-June: 85°F day, 39°F night
  • July-September: 87°F day, 53°F night
  • October-December: 73°F day, 28°F night
Seasonal rainfall averages
  • January-March: 0.31 inches
  • April-June: 0.35 inches
  • July-September: 0.43 inches
  • October-December: 0.31 inches