Define Up South Meaning

Refering to where Virginia is located

As opposed to Deep South. States within the confines of the American South, that border closer to the Northern states, but have strong Southern qualities . Such states as Virginia, Kentucky, parts of Southern Maryland and West Virginia as well. Virginia is a prime example, as it was part of the Confederacy, and parts are heavy in Southern culture, yet borders on Maryland and Washington, DC.

going to the heritage south playground in order to have fun. this phrase is normally used when everyones bored of just chilling in the driveway.

Many residents of Saskatchewan, and in particular, rural residents, use the phrase "up south" instead of 'down south'.

There does not seem to be a distance involved, as in the 'up south' vs. 'deep south' usage in the southern USA.