2025 Compare Cities Overview:
Chestertown, MD vs Annapolis, MD

Are people in Annapolis older or younger than people in Chestertown?
- The Median Age in Annapolis is 1.6 years younger than in Chestertown.

Are housing costs cheaper in Annapolis or Chestertown?
- Annapolis housing costs are 76.1% more expensive than Chestertown housing costs.

Which city has a longer commute, Annapolis or Chestertown?
- The average commute for residents of Annapolis is 0.3 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 Annapolis?
Annapolis, Maryland is situated in Anne Arundel County giving visitors leisure areas such as Quiet Waters Park while also having restaurants like The Boatyard Bar & Grill plus entertainment opportunities at Annapolis Towne Centre.