2025 Compare Cities Overview:
Chestertown, MD vs Charlestown, MD

Are people in Charlestown older or younger than people in Chestertown?
- The Median Age in Charlestown is 3.8 years younger than in Chestertown.

Are housing costs cheaper in Charlestown or Chestertown?
- Charlestown housing costs are 3.2% more expensive than Chestertown housing costs.

Which city has a longer commute, Charlestown or Chestertown?
- The average commute for residents of Charlestown is 7.1 minutes longer than it is for residents of Chestertown.

Things to do in Chestertown?
Chestertown, MD is a charming and vibrant small town nestled in the beautiful Chester River Valley. It has a rich history as one of the oldest towns in Maryland, established in 1706. With its cobblestone streets and historic buildings, it is a pleasure to explore the sights of Chestertown. The downtown area offers plenty of shops, restaurants and cultural attractions to keep you entertained. During the summer months there are an abundance of activities such as farmers markets and festivals to experience. The locals here are friendly and welcoming, making it easy to feel at home when living in Chestertown. Furthermore, with its close proximity to Washington D.C., Baltimore and Philadelphia, Chestertown is an ideal location for commuters looking for a quiet place to call home.

Things to do in Charlestown?
Charlestown is a small, peaceful town located in Maryland’s Eastern Shore region. It offers its residents a relaxed lifestyle with plenty of opportunities to enjoy nature and the outdoors. There are several parks and trails for visitors to explore, including the boardwalk that runs along Charlestown Beach. The town is also home to a wide variety of amenities such as restaurants, cafes, bars, shops, and grocery stores. Charlestown is an ideal place for those looking for a quiet place to call home or a great spot for weekend getaways. Residents enjoy all of these benefits while avoiding the hustle and bustle of larger cities.