2025 Compare Cities Reviews:
Chestertown, MD vs New Windsor, MD

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

I have lived in New Windsor Maryland for the past 20 years and I have watched this town run so many people out, with the high outrageous water bill, ($700) every  More