2025 Compare Cities Overview:
Chestertown, MD vs Chesapeake City, MD

Are people in Chesapeake City older or younger than people in Chestertown?
- The Median Age in Chesapeake City is 17.5 years older than in Chestertown.

Are housing costs cheaper in Chesapeake City or Chestertown?
- Chesapeake City housing costs are 11.9% more expensive than Chestertown housing costs.

Which city has a longer commute, Chesapeake City or Chestertown?
- The average commute for residents of Chesapeake City is 0.8 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 Chesapeake City?
Chesapeake City, MD is an ideal place to live if you are looking for a small-town feel with all the amenities of a larger city. With a population of just over 2,000 people, it’s the perfect size for those who want to branch out into a more rural area while still having access to restaurants and other modern conveniences. The town is also ideally situated on the Chesapeake Bay and offers stunning views in every direction. Known for its outdoor activities like fishing, boating, and bird watching, you can find plenty of ways to enjoy the great outdoors in this quaint corner of Maryland.