I think one somewhat simple interpretation connecting it with actual circles would be as follows:
It is a standard calculus result that the $n$-th term of $\frac{1}{\sqrt{1-x}}$ is $\frac{1}{4^n}\binom{2n}{n}$. For any integer $k$, in the expansion
$$
\frac{1}{(1-x)^{k+1}} = \sum\limits_{n=0}^\infty \binom{n+k}{k} x^n,
$$
the coefficients near $x^n$ asymptotically grows as $\frac{(n+1)\dots(n+k)}{k!} \sim \frac{n^k}{k!}$. For $k=-\frac{1}{2}$ a similar result should stand:
$$
\frac{1}{4^n}\binom{2n}{n} \sim \frac{1}{(-\frac{1}{2})! \sqrt n}
$$
Well, and it so happens that $(-\frac{1}{2})! = \sqrt{\pi}$. Why? The most standard, but not very intuitive explanation is the fact that it is $\Gamma(\frac{1}{2})$, the value of the Gamma function $\Gamma(z)$ in $z=\frac{1}{2}$.
A more intuitive geometric interpretation is shown e.g. in this video. To describe it very briefly, let $S_n(r)$ and $B_n(r)$ be the area and the volume of the $n$-dimensional sphere and ball correspondingly. Then, you can show
$$\begin{cases}
S_{n-1}(r) &= \frac{n}{r} &B_n(r), \\
S_n(r) &= 2 \pi r & B_{n-1}(r)
\end{cases}
$$
Joined together, these formulas yield
$$
B_n(r) = \frac{2}{n} \pi r^2 B_{n-2}(r),
$$
which expands into
$$
B_n(r) = \frac{2}{n} \frac{2}{n-2}\dots \frac{2}{n-2k} \pi^k r^{2k} B_{n-2k}(r).
$$
Note that you essentially divide by $\frac{n}{2}(\frac{n}{2}-1)(\frac{n}{2}-2)\dots$, which simplifies for even $n$ into
$$
\boxed{B_n(r) = \frac{\pi^{n/2}}{(\frac{n}{2})!} r^n}
$$
Then, it is natural to want for this formula to also work for odd $n$, and the most natural way to do this is by defining $(\frac{1}{2})! = \frac{\sqrt{\pi}}{2}$, which will also imply the desired $(-\frac{1}{2})!=\sqrt \pi$.