This is actually possible now (and may have been at the time this question was asked). Simply create a LoadConfig.csx file with the following:
#r "System.Configuration"
using System;
using System.IO;
using System.Linq;
var paths = new[] { Path.Combine(Environment.CurrentDirectory, "Web.config"), Path.Combine(Environment.CurrentDirectory, "App.config") };
var configPath = paths.FirstOrDefault(p => File.Exists(p));
if (configPath != null)
{
// Set new configuration path
AppDomain.CurrentDomain.SetData("APP_CONFIG_FILE", configPath);
// Reset current configuration load state
var t = typeof(System.Configuration.ConfigurationManager);
var f = t.GetField("s_initState", System.Reflection.BindingFlags.Static | System.Reflection.BindingFlags.NonPublic);
f.SetValue(null, 0);
}
Save the file somewhere you'll remember and return to the project you want to load in visual studio. Right click the project and select "Reset C# Interactive from Project". Once the C# interactive window is finished loading call:
#load "C:\path\to\LoadConfig.csx"
NOTE: You must call this immediately after loading the project. If any configuration lookups occur before you load this script then this script will fail to work.
Now the C# Interactive window should have access to your project settings.