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

Are people in Chester older or younger than people in Chestertown?
- The Median Age in Chester is 4.8 years older than in Chestertown.

Are housing costs cheaper in Chester or Chestertown?
- Chester housing costs are 41.1% more expensive than Chestertown housing costs.

Which city has a longer commute, Chester or Chestertown?
- The average commute for residents of Chester is 8.2 minutes longer 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 Chester?
Living in Chester, MD offers a unique and peaceful experience. The small town atmosphere is filled with friendly people and a sense of community that makes it easy to get to know your neighbors. There are plenty of local parks and outdoor activities to enjoy throughout the year, from hiking along the nearby Chesapeake Bay to birdwatching in one of the many nature preserves. The town is also well-known for its delicious seafood restaurants, making it an ideal spot for a date night or summertime lunch. With its affordable housing prices and low crime rate, Chester is an attractive alternative for those looking for a more laidback lifestyle away from the hustle and bustle of larger cities.