Our Story

How Highland Ranch Began

In 2020, best friends Jon Leonardo and Ian Grady set out on a trip that would change everything. Drawn by the adventure, energy, and breathtaking landscapes of Montana, they spent hours exploring Wild Horse Island, hiking its rugged trails, and taking in the expansive beauty of Flathead Lake. Something about that trip felt different—it wasn’t just another adventure; it was the start of a vision.

That experience planted the seed for Highland Ranch, a place where others could immerse themselves in the wild beauty of Montana while enjoying the comforts of state-of-the-art glamping accommodations. More than just a getaway, Highland Ranch is about creating a place that feels like home, where people come to reconnect with nature, make memories, and experience something truly special.

The Birth of Highland Ranch

Some dreams sit on the shelf for years, but for Ian and Jon, the time to create Highland Ranch was now. With a shared love for exploration and hospitality, they saw an opportunity to craft an experience that combined modern design, sustainability, and the spirit of adventure.

Jon, now leading Jupe, a thought leader in the glamping industry, brings his expertise in design, comfort, and outdoor innovation to Highland Ranch. Every aspect of the property is guest-centered, designed to blend seamlessly into nature while offering luxury and convenience. Their goal is simple: listen, adapt, and improve, constantly evolving the guest experience based on real feedback.

Canvas Jupe tent surrounded by trees in Montana’s Flathead Valley

Our Vision & Values

Sustainability

We are committed to achieving a zero-carbon footprint and regenerative farming practices by 2030, implementing eco-friendly systems at every turn.

State-of-the-Art Design

We fuse cutting-edge glamping technology with nature, ensuring guests feel immersed in the wild without sacrificing comfort.

Making Memories

Whether it’s hiking at sunrise, gathering around a campfire, or stargazing under Montana’s vast skies, we want every stay to be unforgettable.

Community & Giving Back

A love for Montana comes with a responsibility to honor and preserve the land. Our future goals include:
Establishing a community garden where guests can engage in sustainable practices and experience farm-to-table living.
Partnering with local conservation and nonprofit efforts to protect and maintain Montana’s wild spaces.
Creating programs that educate and inspire future generations about responsible outdoor recreation.
Private fire pit with seating area at Highland Ranch Montana

The Future of Highland Ranch

Looking ahead, we envision Highland Ranch as a first-rate glamping destination, where visitors come not just for a stay but for a transformational experience. Beyond glamping, our future will include:

Wellness retreats designed to help guests recharge and find balance.

Expanding our outdoor adventure offerings, ensuring guests always have something new to experience.

Cultivating an environment where visitors leave feeling centered, rejuvenated, and inspired.

More than just a destination, Highland Ranch is a place to return to, time and time again. A place where the beauty of nature, the warmth of hospitality, and the thrill of adventure come together to create something truly unforgettable.