2026 Compare Cities Overview:
Middleburg, VA vs Chester, VA

Are people in Chester older or younger than people in Middleburg?
- The Median Age in Chester is 14.3 years younger than in Middleburg.

Are housing costs cheaper in Chester or Middleburg?
- Chester housing costs are 63.3% less expensive than Middleburg housing costs.

Which city has a longer commute, Chester or Middleburg?
- The average commute for residents of Chester is 9.8 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 Chester?
Chester is an historic city located on the south bank of the James River near Richmond, Virginia. It has a rich history spanning centuries that includes both the Civil War and Revolutionary War eras. The city offers all sorts of attractions such as parks and museums where visitors can learn about its past or take part in outdoor recreation opportunities. There are also many delicious restaurants to enjoy while visiting Chester.