2025 Compare Cities Overview:
Winchester, VA vs Oakland, MD

Are people in Oakland older or younger than people in Winchester?
- The Median Age in Oakland is 6.1 years older than in Winchester.

Are housing costs cheaper in Oakland or Winchester?
- Oakland housing costs are 21.8% less expensive than Winchester housing costs.

Which city has a longer commute, Oakland or Winchester?
- The average commute for residents of Oakland is 7.8 minutes shorter than it is for residents of Winchester.

Things to do in Winchester?
Winchester is located in the northern Shenandoah Valley of Virginia. It's a historically significant city known for its rich Civil War history and architectural attractions like Winchester National Cemetery, as well as its numerous outdoor activities like hiking, kayaking, and fishing. The city also boasts an array of art and cultural offerings, with events such as the annual Hillbilly Festival taking place throughout the year.

Things to do in Oakland?
Living in Oakland, MD is a unique and special experience. Located in Garrett County tucked away in the Appalachian Mountains of Western Maryland, the town offers breathtaking views of lush forest-covered mountains and beautiful lakes. The small community enjoys a slower pace of life and is made up of friendly people who take pride in their town. There are plenty of outdoor activities for nature lovers to enjoy, from fishing or camping at Deep Creek Lake to taking a leisurely hike through the woods. You’ll find plenty of local restaurants for a bite to eat as well as specialty shops for all your shopping needs. The area is also rich with history and cultural sites that are worth visiting. Oakland, MD offers something for everyone and is truly a great place to live!