WHIMSY Captured.
We asked you to show us the magic in the everyday, and boy oh boy, you delivered!
Our Whimsy Photo Contest brought in over 500 incredible submissions , each bursting with creativity, humor, and imagination. After much delight (and a lot of difficult choices), the winning images were chosen by your votes on Instagram Stories.
In this blog post, we’re celebrating the talented photographers whose work rose to the top. From surreal moments to playful snapshots, discover the winning entries and top finalists, complete with their photo titles and stories behind each image. Get ready to smile, be inspired, and see the world through a more whimsical lens.
FIRST PLACE: $100
"This picture was taken from the shore of the Vogelmeer - Dutch for 'bird lake' - of which the water level rises during the winter months, resulting in many trees being waterlogged. These two cormorants jumped up to one such tree and started bathing in the sun, which shone from the other side of the lake creating this beautiful and whimsical backlit scene."
SECOND PLACE: $50
You Can't Convince Me Weevils Aren't Just Way Cuter Tiny Elephans
By Radical Noticing
Sweden
"How is this whimsical? I mean look at it. Just look at it. Look at them cute lil legs. Look at that dorky lil trunk."
THIRD PLACE: $25
"Photo taken in the Andes in Peru! I was loopy from altitude sickness, these alpaca were everywhere, and were the goofiest lil goobers I’ve ever met. Loads of derpy personality."
OTHER AMAZING FINALISTS
"Honoring our friends' marriage, we snuck into the forest before the ceremony for a little mischief! We took advantage of the beautiful venue and had to show off the homemade mushy hat."
The Fox with the Blind Eye
By George C
Lawrence, Kansas
@gconover_pics
"A photograph of a red fox standing in a wooded area, showing its one blind eye. This fox and its family lived very close to my home in Kansas, and I would see them regularly around sunset. This particular fox was a resilient parent of three young, and despite its clear visual impairment, still hunted and provided food for its family."
Folk in the Goblins
By Kirby W.
Roaring Fork Valley, Colorado
@k.w.obscura
"This was the only shot I planned on my last desert trip. I’ve always had this cowboy fantasy about a lone traveler living off the land with nothing but a guitar. So I hauled a guitar out to Goblin Valley and asked a friend to throw on a hat and climb a hoodoo at sunrise. The wind was whipping sand everywhere, but the soft light was worth it. Felt good bringing that desert daydream to life."
Golden Hour Gosling
By Reece B.
Ontario, Canada
@reeces.wildlife
"Bathed in soft backlight, this tiny gosling bends toward the earth with determined curiosity — all downy fluff, oversized feet, and serious intent. Behind it, a blurred sibling floats in the glow like a soft echo, more suggestion than shape. It’s a tender moment of exploration, where cuteness meets instinct, and the world is still brand new and full of snacks."
Haven (Safe Space)
By Haven
New York
@havensphotobooth
Diving in Blue Waters
By Harm
Rotterdam, The Netherlands
@Dutchfi3ld
"I just switched my lens to photograph the beach down below, and happened to see 3 boys jumping of the boat. I waited for the right moment and this was the results.How is this whimsical? Just some guys taking a leap of faith to enjoy themselves, just so happens to be at a beautiful spot."
Slot Canyon
By Brent H.
Buffalo, New York
@BrentJHeath
"This particular shot was when Ashley (the subject in the photo) and I were hiking/canyoneering in SW Utah and accidentally came across a few flooded slot Canyons. We had no other choice but to continue through the slot Canyons, risking our electronics getting wet! Fortunately we came prepared and had dry bags. After stuffing our valuables into a safe bag, we dove in and swam through to the end of the hike! This shot was taken before we got wet haha."
Diving for Treasure
By Andrew D.R.
New Jersey, USA
@theunodosreis
"Diving for Treasure” taken on Kodak 400 film at a local pedestrian park while on a walk. The sun was starting to set and made exposure kinda hard, especially with getting birds sharp at this distance. This was one of my first times shooting birds this close using a telephoto lens especially on film. This photo was the only one of ducks that wasn’t underexposed!"
HAPPY STEPPIN'!
-PEPPER 👣

Follow in My Footsteps!
Patreon
If you want exclusive content, behind-the-scenes chaos, and a cozy little supporter-only space, Patreon is where it’s at. It’s like the VIP lounge of Pepper Steps, but with fewer velvet ropes and more lichen facts. You can join for free, so come and hang out!
YouTube
This is my personal favorite spot to be. From functional fitness to educational backpacking vlogs and all of the dorkiness under the sun, I've got something here for you. Grab your favorite trail snacks and stay awhile!
Discord
Wanna chitchat with me? How about thousands of other nature loving friends? From gear talk, to fitness, to backpacking, and heck, even League of Legends (Pepper's favorite video game), there's a whole darn community waiting for you to say hello! What are you waiting for?!
Pep Talks
Need one-on-one advice on social media, hiking, gear, or content creation? Book a Pep Talk with me, and I’ll help you figure it all out. No gatekeeping here my friend, just real advice from someone who’s been there.
See You on the Trail!
Thanks for being here, for supporting this wild journey, and for being part of the coolest little corner of the internet. Whether you're here to laugh at my backpacking mishaps, geek out over plants, or plan your next big adventure, I’m so stoked to have you along for the ride.
HAPPY STEPPIN'!
Pepper 👣
Leave a comment
This site is protected by hCaptcha and the hCaptcha Privacy Policy and Terms of Service apply.