Question pretty much in topic. I’ve tried making roasted squash pieces twice now (once with acorn and once with buttercup) and each time it’s taken me something like 45 minutes of prep time to peel and chop one squash. I’ve got a pretty big peeler, but it’s still really slow to get the stupid thing peeled.
What I’ve been doing is chopping them in half, removing the seeds and other soft flesh, and then trying to peel the halves.
Slice the squash into halves vertically, place them cut side up in a pan with some water, and bake in the oven. Scoop what you want out of the shells after they’ve baked.
Exactly. Bake first, then remove the squash and peel from each other.
terentii is spot on. Once I tried a squash based soup where I didn’t want to bake it first so I did something more like cleaning a melon. With a large knife I cut it down in to small slices. I then used a smaller knife to cut away the flesh from the rind on the smaller sections. It left more “meat” on the skin and was still quite a bit of work. I can’t even imagine trying to peel a squash though. If I was going to try again I think I’d bake it first instead of what I did.
Whack it in half and bake that sucker.
Sometimes I bake them halved, but sometimes I want chunks of butternut for soup. In that case, I cut off the long section. Trim off the vine end, cut it into two (cylinder shaped) pieces, turn each piece on end, and slice the peel from the sides. I do cucumbers like this too. Then I have to deal with the round end, but I usually just whack it in half and then bake and stuff it. Don’t use a peeler; use a big honking knife.
Acorn…just halve and bake it. You’ll make yourself crazy otherwise. 
I love squash season!
Yes.
I admit the last time I needed cooked butternut squash I bought it precooked at Harris Teeter. :o
But if I were to chop it myself, I’ll do as papergirl does.
If you’re making soup and using acorn, butternut or similar squashes, don’t bother peeling, they blend to smooth just fine, and you even up the fibre content of your meal a little.
For something like butternut squash, you can nuke it for something like 5 minutes (pierce the skin first!), let it cool and it should peel easily.
As others have said, the best option is baking them in halves with the peel on.
But if you really want to have peeled chunks, I’d suggest slicing the squash into rings and then peeling the rings. This should enable you to work your knife along the contour of each ring.
yeah bake or steam first and peel or scoop later.
same with pumpkin.
can leave large sections or chunks.
if you want cooked but not baked you can pressure cook it in maybe 10 or 15 minute cooking time.
Sometimes you want roasted chunks of squash in which case the “bake first, then scoop” method doesn’t work at all.
IMO, there’s nothing you can do about an acorn squash, but for a butternut:
One of these will peel it as easily as a regular peel will take care of a carrot. The ceramic blade is just insanely good for peeling.
Try preheating an oven to about 400, get a baking sheet ready, take your chunks of peeled butternut squash, put it in a bowl and add fresh thyme (dried stuff just doesn’t work in this recipe–one of the very few times it doesn’t), salt and pepper. Toss with olive oil to coat and spread in a single layer on the baking sheet. Roast for about 45 minutes, turning every 10 minutes or so, until golden brown and crisp on the outside, fluffy on the inside. So very, VERY good.
Fenris, that recipe is effectively what I’ve been trying to follow (using an America’s Test Kitchen recipe). I think at this point I might just pay the extra money for a prepared squash next time I want to make the recipe.
Professional cook speaking (because I do that a lot here):
Peel the squash out of the grocery bag, and toss it directly into the trash.
BLEH! Squash? GROSS!
Sorry. 
You mistyped.
The correct spelling is “Summer Squash? GROSS!”
Winter squash is sublime.
I think it’s far easier to peel butternut squash whole. Seeding is the easy part. Once you’ve but it in half, it’s slippery and awkward to hold, ergo, difficult to peel.
especially spaghetti squash.
Yes, there are times when you do want the suckers skinless (rindless? shell-less? husk-less?) raw.
Note that the first two cuts crosswise at the ends are practically mandatory for safety sake. You create the base for stability of the thing, and the upper plane allows for a clean cut downwards. Eventually a good enough polygon, with inevitable tiny wastage, is reached by straight cuts.
I do carrots that way, if necessary. And celeriac–now there’s a bitch. Ginger doesn’t need the vertical propping, but most recipes say “peel” but squaring away is quickest and easiest.
Addendum to addendum of above: when you’re dicing onions by 3-d crosscut, or even slicing them when the slice can be a halfsie, the fastest and safest way uses the same idea: slice it in half through the root, and work on each half pressing down on the nice flat bottom, not a roly-poly. The extra two snips of the now-divided vertical ends are done so fast and with less pressure (and safer, of course) it more than makes up for it.
Plus you don’t have to fiddle with getting a grip on some little shred of the peel you open up in the other way; here you have a nice big circle to grab, and the peel comes of in one or two large pieces.
I hate the waste, but I have to remind myself that my time and fingertips are with way more than a few grams of squash or ginger.
What kind of peeler are we talking about? Because I have no problem just peeling butternut with my potato peeler, and it takes, like, 2 minutes tops. Just peel strips from the stalk end to the bottom. Then cut in half and use an icecream scoop to get the seeds/fibres out (which we do not throw away - those are for roasting and salting…)