(1) Most cookies freeze well, so I will put them into Rubbermaid / Tupperware containers in the freezer with waxed paper between the layers. During the Holidays, I may have 6-8 large containers in the freezer (!), but the rest of the year I will usually only have about 2 containers. I ALWAYS have GINGERSNAPS ready to ship (they're my most popular cookies) ~ plus a couple of flavors of MANDEL BROT (mini-biscotti).
(2) I will make up my own ICEBOX SLICE & BAKE LOGS (some are actually rectangles), wrapped well in saran ~ to slice & bake fresh as I need them. Most of the logs can be kept in the freezer, and sliced frozen (just let them thaw about 5 minutes before baking). The Summer Fruit cookies were all my Slice & Bake Logs.
(3) I will have about 5-6 tubs of homemade COOKIE DOUGH in the refrigerator ~ to scoop out and bake as I need fresh cookies. This type of cookie is usually chocolate chip, peanut butter, pumpkin chip, sugar cookie, or something else that's rolled in a ball and gently flattened slightly before baking. When I make the balls, I will roll them either in plain granulated sugar ~ or colored sugar for the season ~ before baking.
TIP: If you want to put SEASONAL SPRINKLES on cookies, bars or brownies (and don't want to frost them), dip the tops of the cookies into the sprinkles BEFORE BAKING (or sprinkle on the brownies before baking), so they'll stick.
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HOLIDAY BAKING SCHEDULE: Many years ago, we used to host gigantic Christmas parties (over 700 people) at our house, with a square dance band and tons of Christmas cookies and cakes that I would bake myself. Although my Christmas baking has scaled way back, I still stick to the same schedule that I did then:
DAY AFTER THANKSGIVING (for about a week), I will make at least 3-4 kinds (or 5-6, if I feel like it) types of cookies as stated above. Then I'll take 1-2 days to make 4-5 different types of fudge and the peppermint marshmallows that my oldest grandson loves. Last, I'll do the SPECIALTY COOKIES ~ formed cookies that take more time and are more "Holiday Specific" (twisted candy canes ~ Whiskey knots ~ Gingerbread cut-outs ~ etc.)
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I buy little cellophane box (Hobby Lobby {wedding supplies} or eBay) that will hold 2 bon bon papers, to put RUM BALLS in, when I put them into cookie boxes or baskets. This is VERY IMPORTANT so that the rum (or brandy) scent doesn't permeate the other cookies! Then write RUM BALLS on top, so the recipient will know what they are and won't give them to children.
If you have friends or relatives who are ALLERGIC TO NUTS OR CHOCOLATE, package those in another box (or separate them in plastic baggies), and write "nuts" or "chocolate" clearly on the box or baggie so that person will know what is ok (or not) for them to eat.
I use square styrofoam boxes for eBay customers (and square tins from Dollar Tree for family & friends). You want SQUARE (or rectangle) so the cookies fit in there better, and they will fit into the shipping boxes better than a round box. I put a long piece of saran wrap on the bottom, and a piece of waxed paper on top of that. Then long strips of waxed paper over and under the rows of cookies (1st photo). Another piece of waxed paper on top (or a birthday or holiday napkin) ~ and the ends of the saran wrap over all. Close the box and tape shut. Put into a big zip-top baggie or other plastic bag.
For the Holidays, you can usually find COOKIE TINS or boxes at DOLLAR TREE ~ or get Rubbermaid containers there. I highly recommend getting SQUARE boxes, tins and containers (NOT round) since they'll fit into shipping boxes better.
There are 2 different priority FLAT RATE boxes for shipping which are best to use ~ so you don't have to weigh them.
All boxes can be ordered from the Post Office's website (FREE) and will be delivered to you by your mail carrier. You can purchase labels on-line from the post office, but they're usually even cheaper if you purchase them from Paypal (and come with tracking & insurance then). You can schedule a FREE pick-up from the post office too! ** I use plastic grocery bags as packaging in the boxes.
I also have a Pinterest board for CHRISTMAS & HANUKKAH COOKIES (but the link won't copy here)