Trailbound Weekly EDITION | 004
This week’s header artwork 🎨 is brought to you by… Holly 🌸 from our Discord Community. She shares, “This was from when we did the South Coast Track (Tasmania) over Christmas and New Year. We’d been climbing up the Ironbound Range since 6am and at around midday we reached the top and the thick cloud lifted just enough to see out to sea.” This sketching prompt was inspired by this idea of seeing what our community sees. How you fill in the blank page is very inspiring to us (Team Trailbound), but we also know it inspires others all over the place! We have a few other submission we are so excited to share, and hope you might play along, too. You can download the above line art here and encourage you to either email or post it under #community-artwork within the Trailbound Discord Server (our weekly email always includes an invitation link).
Hi Friends!
The last time I shared an audio note here, it was well received (Thank you!). Which for me is GREAT! Stringing written words together is not my favorite. However, I love a good voice memo! Below I share some recent thoughts about learning to dance 🕺. Yup! Dancing! No, it’s not about to become Trailbound Dancing. However, who doesn’t enjoy a little shuffle of joy the moment they are on the trail and surrounded by nature?!?
I don’t carry on for too-too long and hope you’ll let me know what you think over in the Discord!
— Max
🤫 pssst… we ARE plotting and planning a Trailbound Podcast for 2026… you can let us know what type of conversations you would like to listen to in the #suggestion-box channel on Discord.
📰 News & Updates 🎭
We don’t create our films or our art for awards or accolades. But… occasionally the story strikes a cord, and a community of people choose to acknowledge the work in a big way. That is exactly what happened with A Little Story About Forever at the Oscars of Environmental Storytelling — Jackson Wild Summit. To be honest, I am still processing the experience of being surrounded by some of my filmmaking heroes in a place as beautiful as Jackson, Wyoming. Photo by Alessandro Ponzo / Jackson Wild
What I do know is that creating a film like this would not have been possible if not for the Trailbound Sketches Community. It would also not have been possible without the support of a brand that cares a lot about doing good so we can continue to do good. If you would like to watch and listen 🎧 to my acceptance speech, you can visit this link and fast forward to 1:52:40.
Our community spans many different parts of the world and walks of life. Some of you are here for the stories I tell and some of you are here to connect or deepen your connection to watercolor painting. No matter how you arrived, it means a lot! Making it possible for us to share important films like A Little Story About Forever, or, Footprints on Katmai. Your participation helps me walk in my late grandmother Lu’s footsteps as I attempt to reconnect with her through any one of her 100+ sketchbooks. Showing up, as we do our best to paint it forward, and share a passion for watercolor painting with all who are willing to make those first scary marks — together.
Opportunities like Jackson Wild feel like ⚡️ lightning-in-a-bottle moments, and if it every happens twice, we know it’ll be something we celebrate as a community.
🥸 Tips & Tricks & Tools 🧰
If you are looking for some playful tips, tricks and ideas to expand your watercolor playtime, look no further than our Discord Community.
Particularly under #art-books where Trailbound Community Artist Brett (see above photo) and others have been exploring the world of block printing X watercolor painting and it’s fabulous! He and fellow community member Neny both shared two fabulous Art Books to inspire others, too. Both the following cover photo images will take you directly to Artist Molly Hashimoto’s website.
🎨 Community Inspiration 🎨
Filling In The Blank Page — Trailbound Community Art Series
Let this be an invitation to play outside of the “lines” of watercolor and be curious! Trailbound Community Artist Jennifer works primarily in clay. However, she also enjoys watercolor and wood burning, too. In the above image she shared her experimentation of mixing both watercolor painting WITH wood burning and find this very inspiring.
Community posts like these are SO COOL. Though, what is even more exciting is to witness so many of you cheering each other on. Sharing your works-in-progress (WIPs) and trailbound adventures with one another.
There are a couple of places to share within Discord:
#community-stories
#community-artwork
🖊️ Inktober X Trailbound 🥾
“Heeerrreeee we go! And now breakfast is half way eaten, but we got the doodle in. Can't wait to peruse all of y'all's.” (The BEST part is perusing everyone’s sketches every day!) ~ Mary Lynn, October 1, 2025
“Not today's breakfast, but one of the best breakfast spots I've had. And the most important part of my breakfast: coffee. The cup perspective took me as long as everything else 😅” ~ Jessica R., October 1, 2025
A little insight into the creating of our inaugural list of Inktober sketching prompts — it came about at the end of a long call discussing all the boring work that takes place to keep Trailbound going in turbulent times.
We (Producer Jennifer and myself) really needed a break and something FUN to talk about. So I was like, “I bet we could come up with at least a handful of fun prompts right now!” We actually got quite carried away, came up with WAY more than we needed, and I almost got in trouble with my wife Eve for working through my block of time being dad. Though, to be honest my son Kip would have LOVED to have helped with this part of dad’s “job.”
Jennifer and I share a lot of the same points of view, but we also see the world through different filters, too. For example when she came up with ‘Breakfast Doodle’ as a prompt, I took it to be sketching what I’m having for breakfast, as did so many of you. However, she saw it as an invitation to “doodle something, anything, alongside breakfast.” The prompt, ‘Breakfast Doodle’ did not have to be a sketch of breakfast, but could be what you personally felt called to sketch while having breakfast.
Do you see where this is going? 😉
At the time of writing this edition, it is DAY 14 of our #sketch-a-day (this is the Discord Channel name for sharing your sketched and connecting with other Trailbound Artist who are playing along). The prompt for that day is ‘Under The Light Of A Silver Moon,’ and it was so cool seeing it being interpreted in different ways!
Inktober sketch by Trailbound Community Artist Dora.
Intober sketch by Trailbound Community Artist Sandy.
All this is to say, we created this list of daily prompts with a hint of Taylor Swift’s mastermind magic! However, the real magic is YOU. There is no wrong or right way to sketch out any one of the daily prompts! It’s ultimately what you feel called to sketch. Furthermore, it does not matter when you start or if life happened and you miss a day here and there.
Come as you are. Sketch when you can. Most importantly, make time for your art the best you can. We will be here for you at any point in your personal journey.
🕵️♂️ Looking For Lu 🥾
Trailbound Community Artist Sherri M shared this beautiful rendition of the ranch in Marble, Colorado my late grandmother sketches many moons ago. This story was featured in our first episode of My Grandmother’s Sketchbook and in Issue 02 of our printed newsletter, Looking For Lu.
Issue 03 of Looking For Lu is still in production. We hoped to have to ready for printing and shipping by the end of October. But a couple of delays with a film production inspired by My Grandmother’s Sketchbook has reshuffled the schedule 🫠. Something tells me you can all relate!
We’ll share more updates as we can!
In other wild and colorful news… I helped make a shoe! It’s kind of a wild story and it is a creative collaboration with Protect Our Winters and KEEN Footwear. You can watch a video of how it came together here!
Below are all the ways to share and connect with us directly or fellow Trailbound Community. Additionally, if you love what we do and would like to support the creation of more free resources and videos, check out the list below.
🤖 Share with our private Trailbound Community in our Discord Server (invites delivered via email).
🔖 Tag @trailboundsketches on Instagram
📨 eMail us at create[AT]trailboundsketches[DOT]com
💌 Snail mail your letters and art work for Max to Trailbound LLC, PO Box 140124, Anchorage, AK 99514
👕 Pick up a Trailbound Sketches Shirt at our new Bonfire Store Front!
🖼️ If you love what we do and would like to support the creation of public access content — Buying art prints goes a long way at covering the cost of creating free YouTube watercolor tutorials. Payment plan options are now available, too.
Stay curious! Have fun! Paint it forward!
Thank you for being a member of the Trailbound Community!
~ Team Trailbound 🎨
