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We study the geometry, topological properties and smoothness of the boundaries of closed $\varepsilon$-neighbourhoods $E_\varepsilon = \{x \in \mathbb{R}^2 \, : \, \textrm{dist}(x, E) \leq \varepsilon \}$ of compact planar sets $E \subset \mathbb{R}^2$. We develop a novel technique for analysing the boundary, and use this to obtain a classification of singularities (i.e.~non-smooth points) on $\partial E_\varepsilon$ into eight categories. We show that the set of singularities is either countable or the disjoint union of a countable set and a closed, totally disconnected, nowhere dense set. Furthermore, we characterise, in terms of local geometry, those $\varepsilon$-neighbourhoods whose complement $\overline{\mathbb{R}^2 \setminus E_\varepsilon}$ is a set with positive reach. It is known that for all bounded $E \subset \mathbb{R}^d$ and all $\varepsilon > 0$, the boundary $\partial E_\varepsilon$ is $(d-1)$-rectifiable. Improving on this, we identify a sufficient condition for the boundary to be uniformly rectifiable, and provide an example of a planar $\varepsilon$-neighbourhood that is not Ahlfors regular. In terms of the topological structure, we show that for a compact set $E$ and $\varepsilon > 0$ the boundary $\partial E_\varepsilon$ can be expressed as a disjoint union of an at most countably infinite union of Jordan curves and a possibly uncountable, totally disconnected set of singularities. Finally, we show that curvature is defined almost everywhere on the Jordan curve subsets of the boundary.