When you stare at a distant building, the Earth curves away beneath your line of sight like a very, very gentle hill. The bottom of the building gets hidden behind this curve. How much gets hidden depends on three things:
1. How far away the building is
2. How tall you are (every inch counts!)
3. How big around the Earth is (the whole point of this)
Simplified: hidden ~ (d^2) / (2R) - h_eye_drop
The clever bit -- using two observation points cancels out errors:
R = (d1^2 - d2^2) / (2 * (h1 - h2))
By measuring from multiple spots and comparing notes, we can solve for R (the radius of the whole dang planet). More measurements = less error, because math is cool like that.
Scientists say the mean radius is 3,959 miles (6,371 km). With careful measurements, you can get within a few percent with nothing but your eyeballs and some basic arithmetic. Take THAT, ancient Greeks. Actually, they figured this out too. Respect.