Journal 77: An Interview with Timber and Jerrilynn Wood

For generations, The Timbers has been more than a restaurant in Cuchara. It has been a place where milestones were celebrated, stories were shared, and memories were made over good food and long conversations. When Timber and Jerrilynn stepped into that story, they didn’t arrive with a background in the restaurant business, but with something just as important: a deep respect for community, a heart for hospitality, and a willingness to say yes to an unexpected calling.

What began as a tongue-in-cheek Zillow listing sent by a sibling quickly became a life-changing decision—one that carried them from Kansas farm country to the mountain valley of Cuchara. In this conversation, Timber and Jerrilynn share how they found themselves here, how they plan to honor the legacy of The Timbers while shaping its future, and what success truly means to them beyond the bottom line.

Interview with Timber and Jerrilynn

Q1. CABIN IN THE PINES: What kind of work did you both do in Kansas before moving to Cuchara to reopen The Timbers?

A1. TIMBER: Jerrilynn spent 20 years as an elementary teacher and 13 years as an elementary principal. I sold farm equipment, and we also managed a small cow–calf herd in Kansas

Q2. CABIN IN THE PINES: What first brought you to Cuchara, and what made this place feel like more than just a stop along the way?

A2. JERRILYNN: Timber and his sister both have unique first names. His is Timber and her's is Drift while their last name is Wood. Growing up, that meant they never found souvenirs with their names on them. Drift’s family are avid skiers, and last year during Spring Break they stopped to ski at Cuchara Mountain Park on their way to Crested Butte. On their drive down the mountain, they noticed The Timbers listed for sale. Drift jokingly sent the Zillow listing to Timber, saying she had finally found something with his name on it.

At the same time, I was preparing to retire at the end of the school year after many years in education. We had talked casually about moving, but nothing had truly captured our attention. When Drift sent the listing, it intrigued us. My Spring Break started the following weekend, so we decided to come to Cuchara and look around. If anything, it was a good excuse to get away for a few days.

Timber contacted Jacky Christian, the realtor handling the listing. We arrived late on a Friday night, Jacky showed us The Timbers on Saturday, and during the drive back to Kansas on Sunday, we made the decision to buy it.

Q3. CABIN IN THE PINES: The Timbers has a deep and rich history in Cuchara. How do you plan to honor that history while also making the restaurant your own?

A3. TIMBER: That balance is something we’re very mindful of. We want to honor the memories so many patrons have of The Timbers by keeping the look and feel mostly the same. In the near future, we hope to add art to the gallery area, and we want people to continue having that same special Timbers experience when celebrating birthdays, anniversaries, and other milestones.

At the same time, we want The Timbers to feel inclusive and welcoming to everyone, not just a place reserved for special occasions. We plan to introduce some fun menu changes over the summer, offer live music, and build relationships with community theater groups to host melodramas and dinner theater.

Q4. CABIN IN THE PINES: Can you walk us through the moment you first learned The Timbers was available and what went through your minds as you considered buying it?

A4. JERRILYNN: Even though we don’t have a restaurant background, we both come from careers centered on customer service. The more I thought about running a restaurant, the more I remembered how often Timber would call or text me in the afternoon saying, “Hey, I’m bringing so-and-so home for dinner tonight. Let me know if I need to stop at the grocery store.” 

We lived 20 miles from the nearest store, yet we routinely pulled meals together on the fly. I convinced myself that if we could do that as often as we did, we could handle this. As we talked more seriously about jumping in with both feet, we grew increasingly excited about the opportunity to live in a beautiful place and work together on something that would be a lot of work, but also a lot of fun.

Both of us came from careers that demanded long hours, so that part didn’t scare us. What felt most intimidating was knowing how special The Timbers is to so many people and realizing we would need to meet that expectation every single day.

Q5. CABIN IN THE PINES: You share a name with the restaurant. Did that influence your decision at all?

A5. TIMBER: Absolutely. If the building hadn’t been called The Timbers, I don’t think we would have given it a second thought.

Q6. CABIN IN THE PINES: For those in Cuchara and Pinehaven who may not have met you yet, what would you like them to know about you and the kind of place you hope The Timbers will continue to be?

A6. JERRILYNN: We’re both people-pleasers and very open to feedback and suggestions. Our goal is for The Timbers to continue being a place where special memories are made. While owning and operating a new business is taking up most of our time right now, we want to be active members of the community.

We’re excited about the possibilities surrounding the ski area and are supportive of those efforts. Timber has applied to volunteer with the fire department, and I hope to get more involved in the community as soon as I have a chance to catch my breath. Giving back matters to us, and we’re very community-minded.

Q7. CABIN IN THE PINES: What does “success” look like for you beyond the business side?

A7. TIMBER: People often say that simply making it through the first year of restaurant ownership is the benchmark for success. For us, success means more than surviving. It means thriving. We hope to provide good-paying jobs for local residents, with opportunities to grow into supervisory or management roles. We believe that can positively impact the local economy.

We also want to offer local musicians and artists a venue to showcase their talents. Ultimately, success would mean The Timbers becoming an integral part of the community and being a true gathering place for families and friends.

Q8.  CABIN IN THE PINES: What important facts would you like the community to know about your restaurant, menu, and hours of operation?

A8. TIMBER & JERRILYNN: Our goal is to be more than just a great steakhouse. We want to offer something for everyone. Quality U.S.-produced beef is at the heart of our menu, complemented by premium wines and spirits, many of them produced right here in Colorado. Draft beer is coming soon, including Mountain Merman beer and other locally crafted selections.

We’re also working to source locally ground coffee and locally blended teas, and homemade sourdough bread will soon become a menu staple. We’ve only been open about 20 days, so our menu is intentionally limited as we monitor sales and fine-tune offerings. By spring, if not sooner, we plan to roll out a full menu with a wide range of options for steak lovers and beyond.

We plan to remain open all winter, serving breakfast and lunch Monday through Saturday. Happy Hour will run from 4:00–6:00 p.m. on Mondays, Tuesdays, and Wednesdays, with dinner service beginning at 5:00 p.m. on Thursdays, Fridays, and Saturdays.

Welcome the Woods

As Timber and Jerrilynn’s story unfolds, it becomes clear that their vision for The Timbers extends far beyond menus and meal service. They see the restaurant as a gathering place and a space where locals and visitors alike feel welcome, where artists and musicians are given a platform, and where employees can grow into meaningful, sustaining work. Their definition of success is rooted in people: shared tables, steady jobs, community involvement, and a restaurant that continues to hold a special place in the hearts of Cuchara and Pinehaven.

In many ways, The Timbers’ next chapter reflects the very spirit that has sustained this valley for generations. The culture of hard work, neighborliness, and the belief that some places matter because of the people who choose to invest their lives there. If Timber and Jerrilynn have their way, The Timbers will remain not just a restaurant, but a living part of Cuchara’s story for years to come.

The Timbers Steaks and Spirits

23 Cuchara Ave E

La Veta, CO  81055

(719) 988-0189

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1. Author’s note: In preparing this article, the author used AI-assisted tools for research support, proofreading, fact-checking, and stylistic refinement. The narrative, analysis, and historical interpretations are the author’s own, and responsibility for accuracy rests solely with the author. The blog’s research methodology statement is available at: https://cabininthepinescuchara.blogspot.com/2019/03/methodology-sources-and-use-of-research.html