How do I select a random value from an enumeration?

Use Enum.GetValues to retrieve an array of all values. Then select a random array item.

static Random _R = new Random ();
static T RandomEnumValue<T> ()
{
    var v = Enum.GetValues (typeof (T));
    return (T) v.GetValue (_R.Next(v.Length));
}

Test:

for (int i = 0; i < 10; i++) {
    var value = RandomEnumValue<System.DayOfWeek> ();
    Console.WriteLine (value.ToString ());
}

->

Tuesday
Saturday
Wednesday
Monday
Friday
Saturday
Saturday
Saturday
Friday
Wednesday

Array values = Enum.GetValues(typeof(Bar));
Random random = new Random();
Bar randomBar = (Bar)values.GetValue(random.Next(values.Length));

Here's an alternative version as an Extension Method using LINQ.

using System;
using System.Linq;

public static class EnumExtensions
{
    public static Enum GetRandomEnumValue(this Type t)
    {
        return Enum.GetValues(t)          // get values from Type provided
            .OfType<Enum>()               // casts to Enum
            .OrderBy(e => Guid.NewGuid()) // mess with order of results
            .FirstOrDefault();            // take first item in result
    }
}

public static class Program
{
    public enum SomeEnum
    {
        One = 1,
        Two = 2,
        Three = 3,
        Four = 4
    }

    public static void Main()
    {
        for(int i=0; i < 10; i++)
        {
            Console.WriteLine(typeof(SomeEnum).GetRandomEnumValue());
        }
    }           
}

Two
One
Four
Four
Four
Three
Two
Four
One
Three