2025 Compare Cities Rankings:
Freeport, ME vs Chestertown, MD

#4 America’s Best Cities for Foodies

#5 Most Secure Places to Live in the U.S. (Large Metro Areas)

#15 Most Secure Large Cities in the U.S.

#20 America's Best and Worst Cities for Crime (Mid-Size Metro Areas)

#21 Most Competitive Private Colleges

#34 Best Green Cities

#81 America's Migraine Hot Spots

#89 Drought-Riskiest Cities

#236 2005 Best Places to Live

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