2025 Compare Cities Rankings:
Chestertown, MD vs St. Charles, IA

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

#6 The Best Cities to Relocate to in America

#12 America's Migraine Hot Spots

#19 Most Secure Places to Live 2011 (Large Metros)

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

#35 Best Block Party Places

#52 2005 Best Places to Live

#54 Most Comfortable Summer Cities

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

#88 Most Popular Cities for the Holidays

#93 Drought-Riskiest Cities

#145 Best Green Cities

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