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5. Winchester, Virginia
Another small town with a big personality is Winchester, Virginia. This city is full of activities a retired senior may enjoy. Spend the day horseback riding, golfing on world class courses, or attending a concert at the nearby venue. Visit the local mom and pop shops, or check out the natural hiking areas that boast clean air. Winchester specifically caters to seniors because such a large portion of the population is 65 and up. With more than 15% of the city over the age 65, it’s easy to make friends in this Virginian town.