This is my version of the Rails rake routes task for Sinatra. I've found this to be endlessly useful in debugging route ordering.

Rakefile

require 'sinatra_app'

# This comes from the sinatra-contrib gem
require 'sinatra/decompile'

# This will print all of the configured routes for the sinatra application in
# the order that the route was first specified. All of the methods will be
# combined together and it will format the output into neat columns. Very useful
# for debugging when an incorrect route is being hit.
desc "List all of the routes configured"
task :routes => [:environment] do

  rl = Default::App.routes.each_with_object(Hash.new([])) do |verb, route_listing|
    verb[1].each do |route|
      route_listing[route[0].source] += [verb[0]]
    end 
  end 
  longest_column = rl.values.map { |v| v.join(", ").length }.max
  rl.each_pair do |route, methods|
    printf("%-#{longest_column}s  %s\n", methods.sort.join(", "), Sinatra::Decompile.decompile(route))
  end 
end