How do you check for intersection between a line segment and a line ray emanating from a point at an angle from horizontal?

Let's label the points q = (x1, y1) and q + s = (x2, y2). Hence s = (x2 − x1, y2 − y1). Then the problem looks like this:

Let r = (cos θ, sin θ). Then any point on the ray through p is representable as p + t r (for a scalar parameter 0 ≤ t) and any point on the line segment is representable as q + u s (for a scalar parameter 0 ≤ u ≤ 1).

The two lines intersect if we can find t and u such that p + t r = q + u s:

See this answer for how to find this point (or determine that there is no such point).

Then your line segment intersects the ray if 0 ≤ t and 0 ≤ u ≤ 1.

Here is a C# code for the algorithm given in other answers:

    /// <summary>
    /// Returns the distance from the ray origin to the intersection point or null if there is no intersection.
    /// </summary>
    public double? GetRayToLineSegmentIntersection(Point rayOrigin, Vector rayDirection, Point point1, Point point2)
    {
        var v1 = rayOrigin - point1;
        var v2 = point2 - point1;
        var v3 = new Vector(-rayDirection.Y, rayDirection.X);


        var dot = v2 * v3;
        if (Math.Abs(dot) < 0.000001)
            return null;

        var t1 = Vector.CrossProduct(v2, v1) / dot;
        var t2 = (v1 * v3) / dot;

        if (t1 >= 0.0 && (t2 >= 0.0 && t2 <= 1.0))
            return t1;

        return null;
    }