The compact complement topology on $X = \mathbb{R}$ is the one where closed subsets are the Euclidean-compact subsets and $X$.
With this topology, any bounded subset of $X$ has Euclidean topology, and so it's clear path-connected.
The compact subsets of $X$ are the Euclidean-closed subsets, and so they can be unbounded. The compact Hausdorff subsets are the Euclidean-compact subsets.
In particular there exist loops $S^1\to X$ with unbounded image.
Partial result: If a loop $g:S^1\to X$ has image bounded from above/below, then it's homotopic to a constant.
Proof: Let $f:[0, 1)\to [0, \infty)$ be an increasing bijection and define $H:[0, 1]\times S^1\to X$ by $H(t, x) = \begin{cases} g(x)+f(t), & t < 1 \\ 0, & t = 1\end{cases}$ then if $g(S^1)$ is bounded from below, then $H$ is continuous. If $g(S^1)$ is bounded from above then replace $g(x)+f(t)$ by $g(x)-f(t)$. To see that it's continuous, consider any Euclidean-compact set $K\subseteq X$, then simply observe that there must be $t_0 < 1$ such that $g(x)+f(t)\notin K$ for $t> t_0$, and so $H^{-1}(K)$ is closed. $\square$
Is $X$ simply connected? As an example of a function which can possibly be not homotopic to a constant map, I propose the map $g:S^1\to X$ defined by $g(1, 0) = 0$ and $g$ maps $S^1\setminus \{(1, 0)\}\cong \mathbb{R}\to X$ where $\cong$ is some homeomorphism. If any maps aren't homotopic, it's the surjective ones.