Over the years, I’ve played around with many winter squash varieties, Here’s a list of favorites, based purely on flavor. In my opinion, acorn squash is the best squash to just bake and eat; the flesh is golden yellow, dry, and sweet, with a definable but pleasant texture.
Butternut squash is very versatile and easy to handle. Its orange flesh is thick, dry, fine-grained, and sweet. Because of its density and ease of preparation, butternut is the squash to use when you want to dice or slice or present squash in any form other than a purée or a roasted chunk.
Hubbard squash is often sold in pieces because it can grow to cumbersome sizes. This popular New England squash usually has a gorgeous, gray-blue shell, with a fine-grained flesh that’s dry, somewhat mealy, and very flavorful. It’s perfect for pies.
A current favorite of mine is an heirloom squash called a cheese squash (or cheese pumpkin). It resembles an old-fashioned flattened cheese box. It’s a good-size squash with tan skin, thick, deep-orange flesh, a coarse texture, and a really sweet flavor.
Sweet dumplings are tiny but great for roasting and presenting whole. Sugar pumpkins are good for pies, too, as well as for canning since they have a thick, fine-grained flesh.
Stay away from pumpkin pumpkins, whether they’re the classic field type or the original French variety. Carve them, but don’t eat them: they’re tough and bland.
Experiment with any new varieties you come across. I love it when my purveyor, Tuscarora Organic Coop in Pennsylvania, delivers a variety of new and interesting winter squash to my door. I like to bake them all and compare them for flavor and texture. You can do the same when serving a wedge of roasted squash as a simple side to roast duck, turkey breast, or pork loin. Pick a few different types at your local farmers’ market and see which one is indeed your favorite.