Algerina Perna, Baltimore Sun
January 22, 2006
Distance from Baltimore: 68 miles, about a 90-minute drive
Why it's worth the gas: Boasting over 300 years of upper Eastern Shore history, this county seat of Kent County is renowned for its historic High Street, above, a brick-lined point of civic pride flanked on both sides (especially as one gets closer to the Chester River) by majestic homes dating back to the 18th century. The town is also home to Washington College, the only college where the use of the name "Washington" was approved by George Washington himself. Dating to 1782, it's the 10th-oldest college in the U.S.
Don't miss: The ducks that congregate at the foot of High Street. They'll welcome you with enough quacking to wake the dead -- suggesting that they're either really glad to see you, or annoyed that you've shown up at all. Also, if you're lucky, catch a performance at the restored Prince Theatre on High Street.
Information: Kent County Visitors Center, 118 N. Cross St., Chestertown, Md., 21620; 410-778-0500 or chestertown.com