At about 1:14 on this clip Entwistle says 'The first job is to reach Ilkley and that swan boat looks past it.' Which to me means more like Lenny is headed to Ilkley from Holmsfirth. With Ilkley being about 1-1/2 hrs North of Holmfirth by car via A62 according to Google map that seems a nice little trip. Looks like it might be possible via rivers Holme, Colme and Calder.
Always liked this episode. I had been under the impression in this episode that Lenny had arrived at Holmfirth from Ilkley via his swan when the guys found him. That he currently lived in Ilkley and had worked at a pickle factory there. Now I am thinking he is originally from Ilkley and had moved to Holmfirth at some time and now wants to float back to Ilkley on a swan to claim his new fame. Maybe he got the inflatable swan from Aunty's.
Is he not the same Lenny we see in another episode as living locally and wanting to be an escape artist? In that episode he seems to live in Holmfirth with his wife and we see his brother(?) again.
I think he could have fit in nicely as another third or fourth man to the group, Barry.