How To Plan The Perfect Sledding Outing

Although you might feel grumpy and disenchanted when the cold weather arrives, there’s something to be said about the first snowfall in Chicago. 

Everything gets quiet and glistens under a frosty white blanket. Okay, maybe the latter part of that sentence is more realistic, but what I’m building up to here is that rather than letting the snow get you down, you can thrill downhill on a speedy fast sled. 

Today, we’re temporarily veering off the topic of gift baskets to focus on our guide to planning the perfect sledding outing.

Choose the Right Gear 

You can’t show up to your favorite hill unprepared. 

Oh no, because sledding is the quintessential traditional and other adjectives ending in “al” activity, so you have to get it right. 

First, you need to choose a sled:

  • Toboggans: Toboggans offer good control with “reins” you can lean into to direct the sled. The toboggan is the classic choice to fit up to four people. The curved front and smooth bottom plow through deeper snow quite well.
  • Sledges: Sledges operate the same way as toboggans but include runners on the bottom without the curved front. They are a good choice for a rider or two.
  • Saucer: The saucer is a disc, ideal for single sledders. However, they can be quite fast. We’re talking Clark Griswold on a trash can lid fast, so not the best choice for small kids or novice sledders.
  • Snow tubes: Tubes are inflatable, offering a nice and comfy ride compared to other sled types. They come in different sizes and shapes but are harder to control and can also go scary fast.  
  • Kicksleds: These are like little chairs on runners. They are easy to operate and designed for a single rider.

The key is to make sure the sled you choose has easy grips to hold onto for safety. A helmet is a must for kids and highly recommended for adults. Sleds pick up speed fast, and noggins must be protected. 

Also, wear SPF sunscreen for your nose and chapstick for your lips. Also, bring along a bottle of water because dragging the sled up that hill is hard work.

Pack Some Food

You’ll want to pack a lunch to refuel and warm up after a few trips down the hill. 

So, what does one include in a winter picnic basket? 

First and foremost, you’ll want a thermos filled with your favorite heartwarming beverage. Hot chocolate is the classic, especially if sledding with kids. But hey, if coffee is the only thing to get you back up that hill, it is just as sled friendly. Teas work, too, as does a nice hot toddy or spiked cider. 

Think simple and transportable snacks, like wraps and sandwiches cut into bite-sized morsels, sausage rolls, little quiches, “hand” pies, cookies, crackers, cheese, etc. Pack everything into an easy-to-carry picnic basket, tote, or duffel bag, along with paper plates and napkins.

Dress for It

Kids are stubborn (if you haven’t noticed), and they may not want to bundle up. Too bad. 

Snow pants keep you warm and dry. Dress in layers, with a thermal shirt and long johns. Also, thick socks and winter boots are a must. Avoid scarves, as they can be dangerous when sledding. Instead, wear a turtleneck or neck warmer. A properly fitted hat that won’t fall over your eyes in mid-descent finishes off your look.


Remember when I said in the intro that I’d be veering off the topic of gift baskets? Well, that was a half-truth. 

It’s still the holiday season, and we’re busting out all the stops with our Let It Snow Holiday Gift Box, stuffed with 2 Walker’s shortbread packs, 2 chocolate covered pretzels; 2 Dolcetto cookie bites, 2 Pirouline wafer two packs, and more!

We are open with limited hours tomorrow and shipping as fast as we can.

Happy Holidays! 

About BasketWorks

BasketWorks is a woman-owned gift basket company located in the north suburbs of Chicago (specifically Northbrook, IL) since 1997. We are proud to offer a variety of gifts and gift baskets appropriate for all occasions. Each of our packages is built to order, allowing for customization at no additional cost to our clients. Contact us today! Please subscribe to our blog post and follow us on Facebook and LinkedIn.

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