Lake, Dale, and Moor: Hiking England Coast to Coast

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In 1972, a 65-year-old retired accountant from Cumbria, Alfred Wainwright, undertook what he called "a harmless and enjoyable walk across England." His route spanned 190 miles, from St. Bees on the Irish Sea across the Lake District, the Yorkshire Dales, and the North York Moors to Robin Hood's Bay, a resort town on the North Sea. His subsequent guidebook to the route, hand-lettered and decorated with exquisitely detailed pen-and-ink drawings, has inspired thousands of pilgrims to repeat his journey, and the so-called "Wainwright's Coast-to-Coast Walk" has become a classic.
The route takes in England's finest scenery, prehistoric ruins, medieval towns and churches, and cozy pubs and inns. You'll walk past Lake Ullswater, an inspiration for Wordsworth, tread mossy limestone in the haunts of beloved veterinarian/author James Herriott, and slink over the bleak plateau of rippling heather roamed by Doyle's fictional man-eating hound. The place names you'll encounter alone justify the trip: Scugdale Beck, Jingling Pot, Puttering Holes, Crinkle Carr, Crackpot Hall, Boggle Hole. (And don't forget Great Tongue.)

Practically Speaking
Armed with Wainwright's book, A Coast-to-Coast Walk, you'll have no trouble doing the route on your own, although reservations at local inns would be a good idea in the summer. (Camping out is a bit dicey; you'll be on private land much of the way. And who wants to lug a heavy pack with camping gear?) Wainwright's first trip took a month, but he is a famous dawdler; two to three weeks should suffice for most people. Count on spending perhaps $50-100 per day for food and accommodations.
Several outfitters offer group trips that cover all or part of the route. You'll have a guide and a van to transport luggage, and all logistics are taken care of. Trips run about two weeks and cost $120-$200 per person per day. An alternative is a self-guided tour arranged by an outfitter, with detailed route maps and instructions, reserved accommodations, and luggage transfers each nightin effect, a regular group trip without the group, the guide, or the fixed departure date. Cost is about $100 per day.
May through September is the ideal time for this trip. It might be possible to push it a month on either end, but remember that days get very short at the high latitude of the route, which is not far from the Scottish border.