October Costume Countdown Walking Challenge

For the past couple of weeks, I’ve been seeing more and more Halloween decorations popping up on my daily walks—from colorful pumpkins to cute inflatable characters to skeletons posed in all kinds of wacky settings. And while I’ll admit that I’ve never been one to go all-in on Halloween decorating, I do love the spooky quirkiness of it all.

You may not be eagerly planning this year’s costume—or inviting your friends over for a Pinterest-worthy Halloween party—but that doesn’t mean that you can’t have a little bit of fun this spooky season.

This month, before you head out on another walk, add a touch of Halloween spirit to your daily stroll by mixing some fun, costume-y touches in with your favorite gear.

Want to Join the Challenge?

All it takes is a little creativity! Each day, choose one of the themes below, and plan your walking gear and/or accessories accordingly. Have fun with it!

Don’t love all of the theme ideas? No problem! There aren’t any hard-and-fast rules about this challenge, so just make up your own—or repeat some of your favorites. This challenge isn’t about costume specifics; it’s about getting out for regular walks and having fun while you’re doing it!

For extra fun, get the family involved! Choose a theme, and see what kind of crazy costumes everyone comes up with for your walk.

Track Your Progress!

I’m a big fan of visual ways to track my progress—so I’ve got a Costume Countdown Tracker for you to use. Just save the image and cross off pumpkins as you try out new themes! You can keep it to yourself or share the image throughout the month to show off your progress.

Don’t Forget the Pics!

Adding some quirky touches to your walking wardrobe is so much fun—but it’s even more fun when you share it! Be sure to take pictures of your Halloween walking adventure! Be sure to include the tags #CostumeCountdown and #WillWalkForCoffeeChallenge and tag us in your posts, so we can see all of your creativity! There might even be a prize for the most creative!

Now for the Themes…

Something Silly:

1) Crazy Hat Day
Cap off your walk (see what I did there?) with a fun hat! It can be a colorful beanie, a baseball cap with a silly slogan, or even a witch’s hat. If you’re more of a headband person, like me, go with your most playful, colorful, or whimsical headgear, whatever that may be.

2) Silly Socks Day
My daughter loves having fun with her socks—and you’ll often find her wearing fuzzy Santa socks with short in the summer or Cheez-It socks on the volleyball court. Take a cue from my kid and pick out some fun socks for your walk. (Bonus points if you wear shorts or capris with wild tall socks!)

3) Clash Day
When I was in school, Clash Day was always our favorite day of Spirit Week. Of course, when we showed up to school in mismatched clothes, everyone else was in on the joke. The people you meet on the trail won’t be. But that’s what makes it even more fun. If you’re feeling timid, though, you can always just wear mismatched socks and call it good.

4) Cozy PJs Day
For most kids these days, every day is Cozy PJs Day. Go ahead and copy your kid for the day and walk in some comfy pajama pants. Or, if you’re feeling extra cozy, just roll out of bed and hit the road in whatever you slept in last night. Just make sure you’re wearing shoes instead of slippers.

5) Rainbow Walk
Recently, we had a whole week of nothing but gloomy days. It’s days like this when you need to go all in on the rainbows. If you don’t have anything with rainbows on it, just dress in as many bright colors as you can—and watch your fellow walkers’ eyes light up with joy (or possibly amusement) as you pass.

6) Stripes and Polka Dots and Paisley, Oh, My!
A little like Clash Day…just with prints and patterns. Mix ‘em up for a wild, playful look on the trail.

7) Silly Sunnies Walk
I never hit the trail without a carefully-coordinated pair of goodrs. If you’ve got an especially colorful pair, you can stick with those—or go with something crazier, from shaped sunnies to oversized sunnies to sunnies with a nose and mustache attached.

8) Fall Comfort Walk
For me, this one won’t take a lot of extra effort, since my fall walking wardrobe is sheer cozy comfort: leggings and hoodies. If you want to go all in on the fall styles, throw on a flannel.

9) Animal Walk
No, I don’t mean walk with an animal (though that’s totally okay, too). I mean dress like an animal. Don ears, a tail, or just an animal-themed shirt.

10) Favorite Food Walk
Wear something celebrating your favorite food: some donut sunnies, a burger hat, a pizza shirt.

Everyday Themes:

11) Sports Fan Walk
October is the start of another NHL season, so you know I’ll be repping my Blue Jackets! But it doesn’t matter if you’re a hockey fan, a football fan, or a frisbee golf fan. Hit the trail in a jersey, hat, or anything else to support your favorite team.

12) Pet Parade
Walking with a four-legged friend? Dress up together!

13) Yeeha!
Hit the trail in your best cowboy style. You might not want to walk in boots, but hats, plaid shirts, and bandannas all work just fine.

14) Candy Colors Walk
If you’ve got something that is actually candy-themed, by all means, wear it! If not, dress in bright, candy-inspired colors to celebrate your favorite sugary treats

15) Fall Fest Walk
You may not dress in cozy sweaters and scarves for a brisk walk on the trail—because you’d probably sweat to death. But choose a day to dress up in your fall faves and stroll with a friend (or your coffee).

16) Twin Day
If you’ve got a walk planned with a friend (or your kid), dress alike! My daughter and I sometimes match when we go on our summer walks, and it always puts a smile on the faces of those we meet on the trail.

In Character

17) Pretty Pretty Princess Day
Hit the trail in your prettiest princess-themed gear—like a tutu and/or a tiara or even just an outfit inspired by your favorite Disney princess. Just leave the glass slippers at home.

18) Superhero Stroll
Wear a superhero-inspired outfit—or maybe a mask or a cape. Feel free to rescue innocent bystanders (or just pet the pups) along the trail.

19) Historical Hero
Add a touch of history to your walking gear to give a nod to a favorite historical figure.

20) Literary Journey
I usually listen to a book while I walk—but I rarely dress like a character in a book. Now’s the time to give it a try!

21) Movie Madness
Just like #18—but less bookish! Pick a favorite movie character!

22) Arrrrr, Matey!
It’s Pirate Day! Wear stripes, add in a bandanna, and add in an eye patch. Parrot optional. Bonus points for greeting fellow walkers in your best pirate speak!

Seasonal Style

23) Pumpkin Parade
Dress in your favorite pumpkin gear—or dress like a pumpkin in all orange! This is also the perfect day to walk with your PSL.

24) Glow Walk
Take an evening stroll and bring all of your glowing gear: reflective items, glow sticks, and flashlights.

25) Spooky Spirit
I always love clothes with bats and skeletons and ghosts when I see them in stores, but then I remember that I’d have a limited time to wear them. Now is that time! Hit the trail in your favorite spooky-themed gear!

26) Witchy Walk
Dress all in black, and wear a hat (or, if you happen to have a witch hat headband, go with that!). Broom optional.

27) Monster March
Pick your favorite monster—or a few different monsters! Add fangs or claws or masks…anything that feels ghoulish.

28) Orange & Black Day
Dress for your walk in traditional Halloween colors!

29) Accessorize!
Wear your favorite costume accessory: a wig, a hat, some ears, or something else. Feel free to mix and match!

30) Wizard Walk
A flowing scarf, a fabulous hat, a magic wand! Don’t forget to bring your magic potion in a colorful bottle!

31) Kids’ Choice
This one is only for the extra daring. Let your kids choose your walking wardrobe for the day. They’ll have a blast styling you!

32) Trick-or-Treat Training
You need to be in shape before the big night! Bring a trick-or-treat bag (or bucket) on your walk. Feel free to fill it with leaves and rocks and other things that you collect along the way.

33) Full Costume Finale
We’ve been building up all month to our big finale! Dress up in costume for your Halloween walk. Bonus points for handing out treats to the people you meet on the trail! (Or just dress up and get your steps while following your kids through the neighborhood at night. It’s not quite as fun, but it still counts!)

Kids aren’t the only ones who can have some Halloween fun! Take advantage of this spooky and whimsical month to change things up for your daily walks! It doesn’t matter if you’re going subtle or over-the-top; adding a Halloween twist to your same old walk is sure to spice things up a bit.

Which themes are you going to try this month? Which ones are your favorites? Which ones would you add?