Everything You Need to Know About Gifting (and Shipping) Holiday Cookies

published Dec 14, 2021
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If you or your loved ones can’t travel this holiday season, sending a box of home-baked sweet treats is a welcome substitute. Tasting your favorite recipes gives those people you’re missing a blissful moment transported into your kitchen, which is true holly jolly magic. It’s also a wonderful way to introduce a tradition for your kids that relatives are sure to love. Cookies decorated by the little ones make a perfect gift that costs little more than postage.

Although imagining those baked goods trekking across the country via the postal service and arriving in mint condition may seem impossible, there’s no miracle to successful holiday cookie gifting and shipping. It’s all about making the right choices, from picking your recipes to selecting the best shipping method for your buck. Fortunately, we’ve done the hard trial-and-error work for you so you can confidently spread your holiday baking love, whether you’re going locally from door-to-door or shipping from coast to coast. 

Choose your cookies wisely

It all starts here. Some cookies and bars are hearty, dense travelers that can not only hold up to the bumps and bruises of the shipping journey, but also have a relatively long shelf life of around a week. Then there are the divas — the beautiful creations like lace cookies, macarons, and linzer cookies that crack in a light breeze, and must be eaten within a day or two of completion, lest they become stale and inedible. 

The good news is, there’s a long list of recipes that work well for cookie gift projects. Move these durable favorites to the top of your list:

One additional note … be mindful of your ingredients, and make sure you’re not sending anything that is extremely perishable, like cookies or bars with cream cheese frostings or fillings. One of my most-requested holiday specialties are these Cranberry “Ecstacy” Bars from The Oregonian, but no one wants the gift of food poisoning, so these ones have got to stick with neighbors and coworkers.

Mail out cookie packages on Monday morning

This is where being a careful planner will save you a sleigh-ful of heartache. You’re going to want to get your parcels to the post office on a Monday morning, so they’ll have a full set of business days to get to their intended destination. Not sure how you’re going to make that deadline? Let me introduce you to our next tip …

Your freezer is your best friend

Freezing cookie dough is simple, and gives you much more flexibility in prepping your items. Once you finish mixing your dough for sugar and gingerbread cookies, it can be frozen in a ball. Wrap the dough in plastic wrap, then thaw to roll out and bake. Drop cookies like chocolate chip, peanut butter, and the like should be portioned into their individual balls, which can be placed on a baking sheet and placed directly in the freezer. You can bake them from frozen by lowering the recipe’s temperature by 20 degrees, then adding 2 to 5 minutes to the overall baking time. Brownies and other bar cookies can be frozen in their pans after baking and cooling. Pre-slice for easy removal. Frozen dough lasts for about 6 weeks, so you can find the cooking marathon time that works for you, and then finish them off the night before packing and shipping. 

Keep it cool

You’ve probably watched enough episodes of “The Great British Baking Show” to know that frosting a warm baked good is a surefire way to fail a challenge. This same rule applies to packing up your treats. Allow yourself enough time so that cookies and bars have fully cooled before they’re prepped for travel, and frosted cookies have had time for the icing to set. This means decorating is best done the night before, while the rest should be done the morning of, if possible. 

Double-up when wrapping cookies

The best way to ship cookies is in pairs, because it makes a sturdier (and more travel-friendly) package. Wrap each individual cookie tightly in plastic wrap, then place two cookies together with the bottoms touching (like you’re making a whoopie pie). Wrap that doubled-up cookie pair in another layer of tight plastic wrap. If possible, do the same with cut-out cookies that are in the same shapes. Brownies and bars, which generally hold their shape better, can be wrapped individually. 

When you’re delivering cookies locally, you can skip the pair-wrapping, but individually wrapping items is still a good idea. It ensures that your items will stay fresh longer, and keeps things from knocking around in the car. It’s not the best surprise to open a box of smeared frosting!

Credit: Shutterstock

Pack as tightly as possible

Here’s where I’m going to give you my trade secrets. Instead of spending a fortune on packing material, all you’ll need is a sturdy cookie tin, a bag of mini marshmallows, old packing or newspaper*, and the medium-sized Flat Rate Priority Mail box provided free of charge from the post office. Start by placing a single layer of mini marshmallows on the bottom of the cookie tin. Carefully place your double-wrapped cookies within it, ensuring that none of the cookie packs are touching. Fill all the space around, above and between the cookies with additional mini marshmallows. Place the lid firmly on top, and give it a shake. Is anything moving? Add more marshmallows. If not, tape the container firmly shut. 

Next, add a layer of wadded up newspaper or packing paper in the bottom of the shipping box. Place the cookie tin inside, then surround and top it with more wadded paper. Close the box and give it another shake, making sure you can’t hear or feel the tin moving inside. If you do, add more paper. When the cookies are safe and snug, tape up the box and address it to its lucky recipient. Now let’s get to the post office!

*Last year I discovered that I was out of paper on my shipping morning, and in a desperate improvisation, used a bunch of diapers in a size my daughter had outgrown. They worked flawlessly.

Ship via USPS Flat Rate Priority Mail

Overnighting any package costs a small fortune, and ground can be too sluggish, especially with the combination of holiday overload and long distances. The best value and most successful method is USPS Flat Rate Priority Mail, which is guaranteed to arrive within 2–3 business days from shipping (depending on how far it’s going). That being said, dates can get pushed this time of year, so bake and ship as early as possible, and remember that receiving a package full of love is always heartwarming, even if it’s a tiny bit stale.

Spread the local love

Don’t forget the people nearby who have brightened another challenging year! Hand-delivered baked goods are a vintage tradition that’s worth revising. To make things less hectic, try to keep your gift-giving list to people within the same general area. If this isn’t possible, consider dividing up your baking and delivering into two separate days, so you’re not spending hours in the car (and getting stuck in seasonal traffic). Plan your route by starting with the farthest location, then working your way back home. If you can, call or text ahead to see if your recipients will be home within your drop-off time. Being able to time your delivery for an in-person, socially distanced holiday greeting makes the entire process much more memorable and special for you, the kids, and your lucky recipients.