2025 Compare Cities Rankings:
Leonardtown, MD vs Chestertown, MD

This is a great place to raise a family. Good schools and lots of  More

I have lived in Queen Anne's county most of my life, which is on the other side of the river from Chestertown. When I was younger, I remember ice cream shoppes, music  More

Chestertown is lovely. Because of the College, it has a real college town feel. It is very old however, so there are many people whose families grew up here. They make  More

Chestertown is lovely. Because of the College, it has a real college town feel. It is very old however, so there are many people whose families grew up here. They make  More