If you do the C2C I am sure you will meet up and make friends with others on the trail and if you wish to opt out after a week there are trains from Kirby Stephen.Are you going to wild camp some nights or just camp on sites?
Start with somewhere that you know well... which in your case happens to be the Peak District. Pack all your gear and sample the stretch of the Pennine Way from Edale to Standedge, and see how it goes after a couple of nights backpacking.
If it goes well, then I'd recommend that you simply follow the rest of the Pennine Way. It's one of the few trails where you can expect to meet someone going your way.
as above. give it a go on a shorter route. wild camping is fine. infact it could be the best bit of any trip. the cumbria way is a lovely walk. i did it from the national park boundary in the south of the county and finished in caldbeck. pick up food along the way in villages you pass through.
hadrians wall is also a shorter one but not as nice as cumbria way.
as for a friend..i would recommend a dog.
Paddy has good advice; the early part of the PW has a rythym to it of pubs and towns for food and resupply.
If you decide on the C2C. Something like -camp site St Bees; pub gardens Ennerdale Bridge and the Bull at Shap. Tea and buns Blacksail YHA. Campsite Patterdale; wild camps nr Kirby Stephen and Swaledale/Ravenseat -more tea and buns. Reeth campsite. Wild camps Farndale (meal Blakey ridge pub) and Gromont.
SD gives some good tips on the Coast to Coast. I backpacked it east-to-west a couple of years ago, and so I may be out of date, but the pub (Fox and Hounds?) in the centre of Ennerdale Bridge had stopped accepting campers and seemed to have become a gastr-pub. I found the Bull in Shap to be very disappointing, as there was dog poo all over the garden. Other than that, I can recommend camping in the garden of the White Swan in Danby Wiske - if the landlord is still Steve, you'll be well looked after.
You could always make up your own route which gives you more freedom. Head to Ambleside or Keswick for instance and you can easily create a 2-3 day circular walk of your own. And you can always change to suit how you're feeling or to take advantage of an unexpected camping spot rather than feeling you've got to push along to the next designated overnight spot.
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