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

Are people in Chestertown older or younger than people in Leonardtown?
- The Median Age in Chestertown is 6.8 years older than in Leonardtown.

Are housing costs cheaper in Chestertown or Leonardtown?
- Chestertown housing costs are 30.2% less expensive than Leonardtown housing costs.

Which city has a longer commute, Chestertown or Leonardtown?
- The average commute for residents of Chestertown is 3.2 minutes shorter than it is for residents of Leonardtown.

Things to do in Leonardtown?
Leonardtown, MD is a wonderful place to live. With its small-town charm and close-knit community, the town is a great place for families to settle down. It has plenty of outdoor activities to enjoy such as fishing, boating and swimming in the beautiful Patuxent River. There are also lots of great restaurants, shops and galleries that make it easy to have an enjoyable time exploring the area. For those who enjoy history, there are plenty of historic sites and buildings such as Leonard Hall Plantation and St. George's Episcopal Church that offer insight into the area's past. The town also has several parks where you can relax in nature or take part in a variety of activities like tennis and disc golf. All in all, Leonardtown is a wonderful place to call home!

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.