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

Are people in Chestertown older or younger than people in Middleburg?
- The Median Age in Chestertown is 13.6 years younger than in Middleburg.

Are housing costs cheaper in Chestertown or Middleburg?
- Chestertown housing costs are 65.3% less expensive than Middleburg housing costs.

Which city has a longer commute, Chestertown or Middleburg?
- The average commute for residents of Chestertown is 7.0 minutes shorter than it is for residents of Middleburg.

Things to do in Middleburg?
Living in Middleburg, VA is a wonderful experience. The small town offers a great atmosphere of community, charm and beauty. The town is known for its Victorian architecture, quaint shops and restaurants, picturesque scenery and equestrian events. There are plenty of activities to choose from no matter what your age or interests might be. You can explore the nearby vineyards or take a horseback ride along the beautiful country roads. In addition to that, residents of Middleburg enjoy a variety of leisurely pursuits such as fishing, swimming, golfing and hiking. So whether you’re looking for a place to relax with family or just have some fun by yourself – Middleburg is the perfect spot.

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.