Before you start waving shears around and pruning raspberries and wineberries willy-nilly, it'd be smart to determine a few key facts that will help you know that what you are doing will improve the health of your bramble fruit. The other option is that you accidentally clip off next year's fruit crop! Yoiks!
Step 1: Are you looking at an everbearer or a biennial?
If you planted it, hopefully you know, but if you inherited it, here's some clues to help you sleuth:
Everbearing raspberry bushes are usually on little dirt hills, though there maybe a full dozen canes coming out of each hill. They also usually have branches, which are usually tied to or woven through some sort of trellis or fence.
Biennial raspberries are more often in a row, though if they've been poorly maintained the "row" will be 4 or 6 feet wide. It'll be hard, perhaps, but pruning raspberries (or blackberries) back to a narrow row again really will ease your harvest (less reaching through prickles!) and improve your crop.
Step 2: Are you looking at a first or second year cane?
Primocanes are the first year canes. They are green and frequently more hairy than thorny in appearance.
For biennials, don't cut these. For everbearers, at the end of the fall, snip off the top 3 or 4 inches.
Floricanes are second year canes. They are brown and fatter. After this year, they will shrivel and die. Snip these to the ground after the berry season is done.
For biennials, you want to start the spring with about 8 canes for every 3 feet of fencerow. For everbearers, thin down to 7 or so canes per hill. The branches of an everbearer can come back to about a foot long also, if you're really on a pruning jag.
Garden Hygiene Moment: collect and burn the snipped canes to reduce pest and disease transfer to your healthy young plants.
Step 3: Consider Your Angle of Cut
You know how you clip roses at a steep angle before you put them in a vase of water? Don't do that here, but for the same reason.
With roses in a vase, your goal is to let the rose drink plenty of water. You clip it at a steep angle to expose a long oval of cut stem to the water in the vase.
When you prune a garden plant, any garden plant, your goal is to minimize the water lost, so you clip at a super flat angle to leave a circular stub. It's as small a wound surface as you can achieve.