Just a little further north, and relatively easy to follow:
Longendale trail from Glossop to the tunnels, then follow the Snow Road to the crossing at Goddard lane, left across Winscar res, left onto Dunford Road, left again following the tracks next to Harden res, out onto Linshaws road, down to the left turning at Ramsden Road, drop down to the house at Ramsden res, left across to the bottom of Holme Moss, down to Holme then left onto Shay lane, Nether Lane and Springs Road, out onto the A635, right at the top of Wessenden, down Wessenden valley, cut across Blakeley res to the Golf club, then up Mount Road to the A62. Left just after Brun Clough res, down Boat Lane to Diggle, canal all the way to Mossley, then cut up to Carrbrook, then Millbrook, through Stalybridge country park, up the valley past Walkerwood, Brushes, lower Swineshaw and higher Swineshaw res, then follow the path over Ogden Brook, Arnfield brook, down Arnfield lane to Tintwistle, inbetween Bottoms res and Valehouse res, out onto the B6105 and back to Glossop.
45 or so miles, not much on road, but CXable all the way.