Dean Shaffer Production

We're very excited to announce that Caleb Kenner has joined the Trails of Tales Songwriter Festival team as the Director of Partnerships & Development! Caleb brings a strong entrepreneurial and communicative background that will enhance our relationships moving forward!

It takes a team, so please welcome Caleb to the crew!!

🤝 Welcome Caleb Kenner to the Trails of Tales Team 🤝

We’re excited to officially welcome Caleb Kenner as our Director of Partnerships & Development for Trails of Tales.

Many of you already know Caleb as an artist who has performed at our 2025 Trails of Tales Songwriter Festival and our Artist Showcase, but he has recently stepped into a larger role as we continue to grow what this brand is creating.

As an entrepreneur and strong communicator, Caleb brings a relationship-driven approach that fits perfectly with the direction of Trails of Tales. He will be helping us focus on partnerships, long-term relationships, and the continued development of the Trails of Tales platform as a whole.

This role is about more than sponsorships — it’s about building meaningful connections that support artists, strengthen our community, and help us continue expanding opportunities for regional talent.

Trails of Tales is not just about a single event or a single stage. It’s about what we are building together for artists and the future of live, authentic songwriting experiences. We’re proud to have Caleb stepping into this role as we move forward!

Dean Shaffer Production

3 days of free live music, and plenty of sights and 🎰🎲!! Make plans to joining us in Deadwood this year, October 15th-17th!

https://facebook.com/events/s/2026-deadwood-trails-of-tales-/1156176569760129/

Trails of Tales Songwriter Festival
Herostock
SneakR Link

🚨 BIG ANNOUNCEMENT 🚨

The 3rd Annual Trails of Tales Songwriter Festival is officially returning to
📍 Deadwood, South Dakota
📅 October 15–17, 2026

Three days.
Multiple historic venues.
Dozens of incredible artists.
One unforgettable weekend of live music and storytelling.

This festival was built to give independent artists a real stage and a real audience — and year after year, the support has grown beyond anything we imagined.

🎶 The best part?
It is completely FREE to attend.
No tickets. No cover. Just authentic music, intimate songwriter rounds, and an atmosphere you won’t find anywhere else.

Our artists travel, perform, and pour their hearts into this event because they believe in what Trails of Tales is creating. If you enjoy the music, we strongly encourage tipping — it goes directly to the performers and helps keep this festival thriving.

👇 MARK YOURSELF GOING & SHARE THE EVENT 👇
https://facebook.com/events/s/2026-deadwood-trails-of-tales-/1156176569760129/�

Inviting friends, sharing the event, and engaging with posts truly helps this grow and reach more fans who love live music.

🤝 We are also actively seeking additional sponsors who want to support independent artists and be part of a rapidly growing regional music event in Deadwood.

Artist announcements, venue reveals, and major updates are coming soon.

Let’s make Year 3 the biggest Trails of Tales yet.
See you in Deadwood. 🎤🔥

Dean Shaffer Production