Winchester, Tennessee Population 7239 is a great city. There is lots to do around Winchester, and within 1.5 hours is Huntsville, Nashville and Chattanooga. The city is full of rich civil war history, and is full of old buildings. 1 cool thing about Winchester is that, unlike many other big cities in the south, you really get the feeling of being in the South.You hear deep accents, see Confederate Flags flying freely and about 100 churches within city limits. It is a great feeling. Also, about the biggest thing in Franklin and Coffee Counties is the lake, Tims Ford Lake. It is huge, has over 300 miles of shoreline, and is a boater and fishers paradise. The town itself is 1 long road, starting in the North with the Wal Mart Shopping Center, continuing on for about 4 miles and ends up on top of a hill, the old town of Winchester. Locals know it as the square.