2026 Compare Cities Overview:
Middleburg, VA vs Annapolis, MD

Are people in Annapolis older or younger than people in Middleburg?
- The Median Age in Annapolis is 15.2 years younger than in Middleburg.

Are housing costs cheaper in Annapolis or Middleburg?
- Annapolis housing costs are 38.8% less expensive than Middleburg housing costs.

Which city has a longer commute, Annapolis or Middleburg?
- The average commute for residents of Annapolis is 7.3 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 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.