In Wolfram Mathematica 14.3, you can now do this with FindShortestCurve provided you account for it returning unevaluated if the locators are not on the region (borrowing the setup code from Lukas Lang's answer) :

(*generate the region*)SeedRandom[1]; numdisks = 60; numpolys = 40; disks = MapThread[ Disk[#1, #2] &, {RandomPoint[Disk[], numdisks], RandomReal[1/5, numdisks]}]; translatePoly[poly_, pos_] := Polygon[# + pos & /@ poly[[1]], poly[[2]]]; polygons = MapThread[ translatePoly[#1, #2] &, {RandomPolygon[8, numpolys, DataRange -> {-.15, .15}], RandomPoint[Disk[], numpolys]}]; start = {-.4, .9}; end = {-.8, -.6}; Graphics[{disks, polygons, PointSize[Large], Cyan, Point[start], Magenta, Point[end]}] (*create the mesh*) mesh = DiscretizeRegion[RegionUnion[Join[polygons, disks]]]; (*use the function*) Manipulate[ Show[mesh, Graphics[{Thick, Red, Dynamic@Evaluate[ With[{fsc = FindShortestCurve[mesh, p1, p2]}, If[Head[fsc] === FindShortestCurve, Point[p1], fsc]]]}]], {{p1, start}, Locator}, {{p2, end}, Locator}] 

---

I came up with an unconventional and inefficient solution that may be susceptible to meshing problems and sensitive to mesh cell size, but I believe it produces a reasonably good short path. Maybe others could improve this or suggest alternative solutions:

SeedRandom[1]; numdisks = 60; numpolys = 40; disks = MapThread[ Disk[#1, #2] &, {RandomPoint[Disk[], numdisks], RandomReal[1/5, numdisks]}]; translatePoly[poly_, pos_] := Polygon[# + pos & /@ poly[[1]], poly[[2]]]; polygons = MapThread[ translatePoly[#1, #2] &, {RandomPolygon[8, numpolys, DataRange -> {-.15, .15}], RandomPoint[Disk[], numpolys]}]; start = {-.4, .9}; end = {-.8, -.6}; Graphics[{disks, polygons, PointSize[Large], Cyan, Point[start], Magenta, Point[end]}] mesh = DiscretizeRegion[RegionUnion[Join[polygons, disks]]]; cells = MeshCells[mesh, 2][[All, 1]]; prims = MeshPrimitives[mesh, 2]; meshcentroids = RegionCentroid /@ prims; nprim = Nearest[meshcentroids -> "Index"]; startcell = cells[[First[nprim[start]]]]; endcell = cells[[First[nprim[end]]]]; connectedCells[cells1_, cells2_] := Length[Intersection[cells1, cells2]] == 2 cellGr = RelationGraph[connectedCells[#1, #2] &, cells, VertexCoordinates -> meshcentroids]; path = FindShortestPath[cellGr, startcell, endcell]; Show[Graphics[ {EdgeForm[LightRed], FaceForm[LightYellow], mesh, PointSize[Large], Cyan, Point[start], Magenta, Point[end]} ], HighlightGraph[cellGr, PathGraph[path]] ] 

The above code finds a path in the mesh connectivity graph. That is the graph of adjacent triangles (sharing an edge) in the discretized mesh. This path is obviously very squiggly, so the following code tries to find the longest 'leaps' along the path that can skip out vertices but stay within the region:

(** from the currentPoint, try to draw a line that to the furthest possible point on the path that stays within the region **) getcoords[cell_] := AnnotationValue[{cellGr, cell}, VertexCoordinates] pathcoords = Join[{start},getcoords /@ path, {end}]; maxiline[currentPoint_, coords_] := SelectFirst[Reverse[coords], Quiet[Check[RegionWithin[mesh, Line[{currentPoint, #}]], False]] &] lpath = NestWhileList[maxiline[#, pathcoords] &, start, # != end &]; Graphics[{mesh, Red, Line[lpath], PointSize[Large], Cyan, Point[start], Magenta, Point[end]}] 

here is a first try. It can be improved, but one has to start somewhere. The following program takes a region, a start and end point and a step size. It makes a plot of the path (red) and the tried points (green). But take car, because there are no preconditions to exploit, it takes a lot of steps. It is a recursive program, therefore we need to enlarge "$RecursionLimit". Take care with "stepsize", make it as big as reasonable, otherwise the number of steps will explode. Further, the difference in x and y coordinates between start and endpoint must be a multiple of the stepsize. Otherwise the end is never found. And for simplicity, the start point should be chosen above the end point. Note also that the path can be pretty big, so it make no sense to print it. The idea is, that you will do something with it besides printing. Further, you will need some real region, not translated polygons, that will work with "RegionMember". Here is the program, have fun:

getPath[region_, start_, end_, stepsize_] := Module[{path = {pos = start}, step = stepsize, wrong = {}, remem, search}, If[Mod[(end - start)/step, 1] != {0, 0}, Print["Difference between end and start must be a multiple of \ stepsize."]; Return[]]; remem = RegionMember[region]; search[pos_] := Module[{}, If[ Norm[pos - end] < 0.001, Return[{}]]; Which[ tp = pos + {0, -1} step; ( ! MemberQ[path, tp]) && ( ! MemberQ[wrong, tp]) && remem[tp], AppendTo[path, tp]; search[tp], tp = pos + {1, 0} step ; ( ! MemberQ[path, tp]) && ( ! MemberQ[wrong, tp]) && remem[tp], AppendTo[path, tp]; search[tp], tp = pos + {-1, 0} step; ( ! MemberQ[path, tp]) && ( ! MemberQ[wrong, tp]) && remem[tp], AppendTo[path, tp]; search[tp], True, AppendTo[wrong, path[[-1]]]; path = Delete[path, -1]; If[path == {}, Return[{}]]; search[path[[-1]]]; ]]; search[start]; Show[Region[region], Graphics[{Green, Point[wrong], Thick, Red, Line[path], Black, PointSize[0.03], Point[end] , Point[start]}], PlotRange -> {{-1, 4}, {-1, 5}}, Axes -> True] // Print; path ]; 

We create some arbitrary region, choose a start and end point and let the program search a path.

region = RegionUnion[Disk[{0, 3.2}], Disk[{0.9, 2.2}, 0.5], Disk[{1.9, 3.}, 0.8], Disk[{2.5, 1.8}, 0.6], Disk[{1.8, .6}, .9], Disk[{0, 0}]]; start = {0., 3.2}; end = {0, 0}; stepsize = 1/10; $RecursionLimit = 10^4; path = getPath[region, start, end, stepsize]; 

Start with this:

RegionUnion[Disk[{0, 0}, 2], Disk[{3, 0}, 2]]; Region[%] 

For a simple circle and a point:

RegionDistance[Disk[{0, 0}, 2], {3, 0}] 

1

Graphics[{Disk[{0, 0}, 2], Point[{3, 0}], Red, Line[{{0, 0}, {3, 0}}]}] 

If the main intention remains to work with Random-function the ideas of @flinty are not bad to look whether these are connected and a path exists.

This is the generated approach to a plane geometric arrangement of Circle and Polygon. For each the center is known and a Sort or else is easily done.

This process have to be repeated with care for each smaller set that works.

Dealing with Transform fails for BooleanRegion.

ℜpolygon = Region@RegionUnion[ Table[Polygon[ Plus[cent[[i]], #] & /@ RandomReal[{-0.15, 0.15}, {8, 2}]], {i, 30}]] ℜcircle = Region@RegionUnion[ MapThread[ Disk[#1, #2] &, {RandomPoint[Disk[], numdisks], RandomReal[1/5, numdisks]}]] ℜcomp = Region@RegionUnion[ℜpolygon, ℜcircle] 

But RegionNearest and RegionDistance do not work, are not defined for BooleanRegion.

RegionDistance[ Region@RegionUnion[{Disk[{0, 0}, 2], Disk[{1, 1}, 2], Disk[{1, -1}, 2]}], {3, 0}] Graphics[{Disk[{0, 0}, 2], Disk[{1, 1}, 2], Disk[{1, -1}, 2], Point[{3, 0}], Red, Line[{{Sqrt[(3/2 + 1/10 (-5 - 4 Sqrt[5]))^2 + (-3 + 1/5 (5 + 4 Sqrt[5]))^2], 0}, {3, 0}}]}] 

This too must be a BooleanRegion.

Mathematica V12 has the built-in RandomInstance and GeometricScene

RandomInstance[GeometricScene[{a, b, c, d, g, e, f}, { a == {-1/2, 0}, b == {1/2, 0}, Line[{f, a, b, e}], p0 == Polygon[{e, g, f}], p1 == Style[Polygon[{a, c, b}], Yellow], p2 == Style[Polygon[{b, d, c}], Magenta], p3 == Style[Polygon[{d, c, g}], Green], p4 == Style[Polygon[{g, c, a}], Blue], p5 == Style[Polygon[{e, b, d}], Purple], p6 == Style[Polygon[{g, a, f}], Orange], GeometricAssertion[{p0, p1, p2, p3, p4, p5, p6}, "Similar"]}], RandomSeeding -> 4] 

It has the built-in GeometricAssertion with offers a generative process to construct the path along with the objects. And this allows nicer and more realistic random polygons. And it provides a description of the paths in the plane and it handles more geometric relations i. e. SimplePolygonQ.

Splice might be reintroduced on V12.1 and later. I can be found in other answers to question on this community. Sequence@@ old style.

AnnotationValue is not in my documentation of Mathematica V12.0.0. But AnnotationValue works on V12.0.0. So this is a built-in without value in this question: Failed.

So the rest does not work.

This works on V12.0.0 and alike:

Show[Graphics[{mesh, PointSize[Large], Cyan, Point[start], Magenta, Point[end]}], Subgraph[cellGr, PathGraph[path]]] 

Using

connectedCells[cells1_, cells2_] := Length[Intersection[cells1, cells2]] == 1 

in the above use code gives:

Show[Graphics[{mesh, PointSize[Large], Cyan, Point[start], Magenta, Point[end]}], Subgraph[cellGr, PathGraph[path], EdgeStyle -> {Thick, Green}]] 

This is faster, but still has the problems in the lower left part of the DiscretizeRegion.

mesh = DiscretizeRegion[RegionUnion[Join[polygons, disks]], MaxCellMeasure -> 1]

mesh = DiscretizeRegion[RegionUnion[Join[polygons, disks]], MaxCellMeasure -> {"Length" -> 1/15}, PrecisionGoal -> None]; cells = MeshCells[mesh, 2][[All, 1]]; prims = MeshPrimitives[mesh, 2]; meshcentroids = RegionCentroid /@ prims; nprim = Nearest[meshcentroids -> "Index"]; startcell = cells[[First[nprim[start]]]]; endcell = cells[[First[nprim[end]]]]; connectedCells[cells1_, cells2_] := Length[Intersection[cells1, cells2]] == 1 cellGr = RelationGraph[connectedCells[#1, #2] &, cells, VertexCoordinates -> meshcentroids]; path = FindShortestPath[cellGr, startcell, endcell]; Show[Graphics[{mesh, PointSize[Large], Cyan, Point[start], Magenta, Point[end]}], Subgraph[cellGr, PathGraph[path]]] 

This shows that adaptive meshing has to be replaced by a fine mesh of regular density for the most optimal path if triangularization is used. Every corner, every smaller trespassing, every extension pointing inward or outward attracts the triangulation mesh, and there induces an oscillation in the shortest paths.

A regular does lead to oscillations as long as the cell measure is high. For smaller once the shortest stops from oscillating and gets direct and stays inside the meshed blob. If the boundary would be taken better into account the shortest might stay more in the blobs center region.

It is a compromise between time and directedness how short the shortest path will be.