I planted garlic for the first time a year or two after I moved to Portland -- so in 2003 or 2004. Ever since then I've devoted a good section of my garden to it. I've tried my hand at fall and winter gardening -- building cloches and other contraptions to keep the veggies warm enough and protected from the weather -- but I've never been all that successful. These days I usually just plant a lot of garlic in the fall, broadcast my cover crop seeds, and then call it quits in the garden until the following spring.
I planted this year's garlic last weekend (I usually plant it mid-October) -- 60 early Italian softnecks in a sheet-mulched bed in the front and 16 Musik hardnecks in a smaller sheet-mulched bed up front. I still have a couple heads of the Musik hardnecks left and I think I'll plant those in the back somewhere. I always like to plant a mix of hardneck and softneck because I like the hardneck for the scapes (I make them into pesto and also sautee them) and flavor and I like the softnecks for better storage and braiding.
Here's a trick I learned last year -- MULCH! I know that's not really a trick -- it's more of a given for most gardeners but I wised up to it late. I mulched my epic garlic crop last year with a couple inches of straw and those garlic heads were bigger than any I've ever grown before. Mulching keeps the beds relatively weed free (garlic doesn't like competition), keeps the soil from compacting and also keeps it a bit warmer.
I plant most bulbs -- including garlic -- about 2-3 times their depth. So I usually plant my garlic about 2-3 inches deep with the skinny end (you know, the end that sprouts if don't use your garlic fast enough) pointing up. This year I mixed a small handful of all-purpose organic fertilizer into each hole with loosened soil. After planting all the garlic, I covered the beds with a thin layer of compost, and finally layered them with a couple inches of straw. I don't always fertilize but it's a good idea. A lot of folks side dress their garlic at intervals throughout the year as well but I never do and I've always had good results.
Most varieties of garlic will poke their green heads out in a few weeks -- usually by Thanksgiving if you've planted them early-to-mid October -- but once it gets cold enough they stop growing. Most of garlic's growth is in the spring which is why some people plant it then. I've never done that but I don't think the flavor would be as good or that the garlic would get as big with a spring planting.
One of my favorite homemade spring foods is garlic scape pesto -- made from the spiraling seed heads that you want to cut off whether you cook with them or not. If you don't snip them off the energy goes to flowering rather than to the garlic head.
One more quick thing. Planting supermarket garlic is a gamble because a lot of commercial garlic has sprouting inhibitors meaning it won't grow or won't grow well. If you plant grocery garlic just be sure it's organic and then you've got a green flag. I often use market garlic for my softnecks but I always buy my hardneck garlic at nurseries. Mostly because there's more variety and it's not so easy to find hardneck garlic in markets.
Go plant some garlic!