Personally equipment wise I would recommend.
Pair of boots (my 10 year old £20 boots are more comfortable than my £120 'decent' boots)
Decent walking socks
Pair of walking pants
fleece
hat/gloves
water proof jacket and pants
hydration pack (so your not carrying heavy plastic bottles of water)
rucksack (about 30 litre)
a dry bag for inside your rucksack to put clothing/car keys/money etc
Compass
I've also been converted to using a walking pole after initially taking the piss out of mates, takes a lot of pressure off the knees when you're coming down a steep hill.
You can print out maps and routes on the internet, if you do decide to buy the os maps get them laminated so they dont get pissed wet through.
People say start off with smaller walks but my first walk 2 years ago was snowdon and since then I've done many harder walks and I wouldn't consider myself fit. I took my missus up to helvellyn via striding edge last week and that was the first proper walk she had ever done. Just take your time but leave yourself enough time to get down before it gets dark.
Learn how to read a map and use a compass and be able to read OS grid references.
Check the weather forecast before you go, what can be a moderate walk in normal conditions can be death defying in ice and snow without the proper gear (crampons ice axe etc).
Some good walks on the website below. If you live in heywood then pendle hill aint that far away and is a decent walk and you could do it without buying all that gear I mentioned.
http://www.walkingbritain.com/