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Jumping for a Cause: The Seward Polar Bear Jump Off and My Mission to Make a Difference
Join Artwork by Sierra Winter at the 2025 Seward Polar Bear Jump Off! Jumping for cancer research in honor of "The Troll."

Sierra Winter
Oct 29, 20243 min read
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Dad's Sayings, Saying Goodbye
I miss you every day, Dad. Your sayings, your humor, and the way you loved life. You’ll always be with me, in my heart and memories.

Sierra Winter
Oct 21, 20245 min read
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Celebrating the Life of OC - My Dad - The Troll
This weekend, we honored my dad, OC, surrounded by love despite the cold. Thank you for sharing your stories and memories of his adventurous

Sierra Winter
Oct 14, 20245 min read
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Exciting Growth and Collaboration: Sierra Winter and Arctic FX Graphics
I am beyond thrilled to share some major developments happening with Artwork by Sierra Winter ! My latest partnership with Arctic FX...

Sierra Winter
Sep 18, 20243 min read
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Finding Self-Love, Trust, and Confidence: The Foundation of the Laid Back Ladies Ride
Riding a snowmobile through the backcountry is exhilarating, empowering, and, at times, a little daunting...

Sierra Winter
Aug 30, 20242 min read
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Dear Troll,
I have been really worried about my dad lately, something in my gut keeps telling me to spend as much time with him as possible. His...

Sierra Winter
Jul 29, 20248 min read
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Sunflowers in the Rain
Something you might not know about me (because I rarely share this side of me) is that I sometimes process my feelings by singing to...

Sierra Winter
Jul 9, 20242 min read
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To The Top - An OC Original
Stars fill the sky, the moon gives some light. Ice crystals floating all around. Snow squeaking under foot. Frost clouds in your face....

Paul O'Connor
May 5, 20241 min read
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The Awakening of Winter
I awaken from my slumber, winter waits at my front door. It only snowed a few inches, I am constantly craving more. A message to my crew,...

Sierra Winter
Nov 12, 20231 min read
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The Girl Behind The Screen
To the girl behind the screen, I wish I had your hair. It shimmers in the sunlight, Not a stray here nor there. To the girl behind the...

Sierra Winter
Jul 29, 20232 min read
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Icey Fishing
It was around 1984 and my son, PJ, was 2 years old. I decided to go to Lake Louise to fish for burbot and lake trout in an ice house that...

Paul O'Connor
May 25, 20235 min read
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I LOVE YOU!
I had a random urgency to call my dad late in the afternoon. Knowing it was long past his 'quitting time' and expecting him to be asleep...

Sierra Winter
May 16, 20234 min read
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Babysitting with Bears 1986
I was working for Moose Horn Lodge located 5 miles south of the Talachulitna along the foothill so Beluga Mountain. We were on 7-Mile...

Paul O'Connor
Feb 10, 20233 min read
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Wild Thing - 1983
Around 1983 the Bureau of Land Management decided to bring some wild mustangs from Arizona to Alaska to give them a home instead of...

Paul O'Connor
Feb 8, 20232 min read
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Welcome to Sierra Winter's Story
Welcome to my website and thank you for taking a look around. I am really proud of how far my art business has grown and I am more proud...

Sierra Winter
Oct 21, 20224 min read
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