2025 Compare Cities Overview:
Chestertown, MD vs Winchester, VA

Are people in Winchester older or younger than people in Chestertown?
- The Median Age in Winchester is 2.5 years younger than in Chestertown.

Are housing costs cheaper in Winchester or Chestertown?
- Winchester housing costs are 6.0% more expensive than Chestertown housing costs.

Which city has a longer commute, Winchester or Chestertown?
- The average commute for residents of Winchester is 2.0 minutes shorter than it is for residents of Chestertown.

Things to do in Chestertown?
Chestertown, MD is a charming and vibrant small town nestled in the beautiful Chester River Valley. It has a rich history as one of the oldest towns in Maryland, established in 1706. With its cobblestone streets and historic buildings, it is a pleasure to explore the sights of Chestertown. The downtown area offers plenty of shops, restaurants and cultural attractions to keep you entertained. During the summer months there are an abundance of activities such as farmers markets and festivals to experience. The locals here are friendly and welcoming, making it easy to feel at home when living in Chestertown. Furthermore, with its close proximity to Washington D.C., Baltimore and Philadelphia, Chestertown is an ideal location for commuters looking for a quiet place to call home.

Things to do in Winchester?
Winchester is located in the northern Shenandoah Valley of Virginia. It's a historically significant city known for its rich Civil War history and architectural attractions like Winchester National Cemetery, as well as its numerous outdoor activities like hiking, kayaking, and fishing. The city also boasts an array of art and cultural offerings, with events such as the annual Hillbilly Festival taking place throughout the year.