2026 Compare Cities Overview:
Winchester, VA vs Oakland, TN

Are people in Oakland older or younger than people in Winchester?
- The Median Age in Oakland is 1.2 years older than in Winchester.

Are housing costs cheaper in Oakland or Winchester?
- Oakland housing costs are 3.5% less expensive than Winchester housing costs.

Which city has a longer commute, Oakland or Winchester?
- The average commute for residents of Oakland is 11.4 minutes longer 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, TN is a great experience. The town has plenty of amenities to offer its residents, including parks and outdoor recreation areas, shops and restaurants, and plenty of places to get involved in the community. The people are friendly and welcoming, making the town feel like home. The weather here is generally mild with hot summers and cold winters. It’s a great place to raise a family due to its low crime rate and safe neighborhoods. Best of all, the cost of living is incredibly affordable compared to other cities in the area. All in all, Oakland, TN offers something for everyone - whether you’re looking for an opportunity to relax or explore new things.