Is there a difference between the calculated value of Pi and the measured value? The mathematical value of Pi has been calculated to a ridiculous degree of precision using mathematical methods, but to what degree of precision has anyone actually measured the value of Pi (or at least the ratio of diameter to circumference), by actually drawing a circle and then measuring the diameter and circumference?
If these two values differ, is the resulting difference (discounting inaccuracy in measurement) the result of the curvature of the surface on which the circle is drawn, or in the case of a circle in space in zero gravity (as much as that can exist), the curvature of space-time?

There's an underlying error in the question, namely the assumption that being in a curved space would result in a "different measured value of $\pi$".
What happens in a curved space is that the ratio between a circle's circumference and diameter is no longer the same for all circles. More precisely, the ratio will depend on the size of the circle. For small circles (with diameter tending towards 0) the ratio will converge towards the one unchanging mathematical constant $\pi$ -- as circles get larger the ratio will either become larger and smaller according to whether the curvature of space is negative or positive.
However, $\pi$ as the limit of $\frac{\text{circumference}}{\text{diameter}}$ for small circles is the same mathematical constant for all possible curvatures of space.
According to the General Theory of Relativity we live in a slightly curved space. This has been measured directly in the vicinity of Earth by the Gravity Probe B experiment. The experiment didn't actually measure the circumference of a large circle, but the results imply that the geometric circumference of a circle approximating the satellite's orbit around the earth is about one inch shorter than $\pi$ times its diameter, corresponding to $\frac CD\approx 0.9999999984\, \pi$. (The curvature is caused by Earth's mass being inside the orbital circle. A circle of the same size located in empty space would have a $\frac CD$ much closer to $\pi$).

Science fiction authors sometimes get this wrong. For example in Greg Bear's Eon there's a mathematician character who concludes she's in a curved area of space by measuring the value of $\pi$ and getting a nonstandard value. I headdesked -- it doesn't work that way.
