Guides to the trail

Waypoint 51 has a great short guide to the trail including a section on walking with a dog.
Becky the Traveller has a guide to wild-camping on the Pennine Way, which includes a kit-list, financial breakdown and other hints.
The Rambling Man website has an excellent one page guide to the Pennine Way which provides clear information for planning the walk.
The National Trails website contains an official page for the trail. This includes up to date information on path closures and diversions.
I use the Trailblazer Pennine Way guide for all my walks on the Pennine Way. It contains useful hand-drawn maps of the route, along with accommodation and planning information. Highly recommended.
There is also an official Nation Trail guide produced by Damien Hall.
Another popular guidebook is the Cicerone Pennine Way Guide
Cicerone has produced a Pennine Way Map Booklet which contains the Ordnance Survey 1:25000 scale maps for the route, saving money and hassle in comparison to buying the sheet maps.

Package Options

Various companies provide package options for walking the trail, where all accomodation is booked in advance:

The Barefoot Backpacker (2019)
There is a detailed account on pennineway.net of the walk, including photos (2019)
Jasmin Paris’s account of her 2019 vistory in the Spine race is a must-read. This is one of the most-gruelling races in the world, and Paris pulled off a stunning upset. (2019)
penninewayers describes what happened on Steve, Derek and Tim’s second attempt to walk the Pennine Way after poor weather stopped their first attempt. (2015)
stottie walks describes two hikes on the Pennine Way, the first in 1963 and the second 50 years later for the trail anniversay (2013/1963)
Martyn at trailplanner wrote his account of completing the trail in 14 days (2014)
The Legs That Make Us was a ‘performative journey’ carried out by artists Tamara Ashley and Simone Kenyon along the Pennine Way (2006)
Pennine Way Walk describes a charity walk on the trail by Catherine and Andy (2003?)
John A. Butler walked the Pennine Way as part of a series of walks along the length of the country. (1988)
50 Steps was a performance piece, subtitled ‘Walking and Dancing the Pennine Way’ which took place in 2015, but very little information is available online. The Northern Echo has written about it.

The Pennine Challenge (Youtube link) is a 1982 documentary about four young people walking the Pennine Way. The conditions they face in August gives an idea of how tricky the route could be before the flagstones were in place. It’s also interesting to see how different documentaries were in the 80s.
The Pennine Way from the Air is a fantastic 43-minute aerial tour of the Pennine Way.
Paul Rose presented a four part BBC series celebrating the Pennine Way’s 50th anniversary.

The Pennine Way: The Pennine Way: The Path, the People, the Journey by Andrew McCloy is an account of the walk with a great deal of background information about the trail. Highly recommended.
One Man and His Bog is a book about travelling the Pennine Way in the ‘bad old days’ when the early stages did not have flagstones. The writer did not seem to enjoy hiking very much. While the humour didn’t work for me, the goodreads reviews suggest many people disagree with me.
The Publishing History of Wainwright’s Pennine Way Companion.
Leeds University Library holds the Walking Home Archive, consisting of physical and digital materials relating to Simon Armitage’s book Walking Home. Some of this material can be viewed online.