We are Peak
Damon Kupper has been leading engaging sightseeing tours of Portland, Oregon, since 2005, combining his passion for history with a talent for storytelling. His expertise in entertaining groups was first cultivated while performing as a busker across Europe. A dedicated history enthusiast, he describes himself as an "edu-tainer," blending education and entertainment to create dynamic, insightful, and memorable tour experiences.]
Together with his partner, Heather Rose of Bespoke Oregon Travel, they founded Peak Tours to deepen meaningful engagement with the community, and to share fabulous Portland, Oregon, with visitors from around the world.
The Peak Team
Eric Tobar has been guiding visitors through Oregon since 2022 and has been a guide with Peak Tours since 2023. A former chef with a passion for Oregon wine, local food, history, art, and the natural world, Eric specializes in creating unforgettable experiences beyond the typical sightseeing tour. From Portland City tours to custom North Willamette Valley wine tours and scenic adventures to Mt. Hood and the Oregon Coast, he loves sharing the hidden gems, fascinating stories, and local flavors that make Oregon one of the most unique places in the country.
Leo Schaefer has been getting to know Portland since moving here 34 years ago. Born and raised in Montana, he has always loved to travel and says, "The next best thing to traveling is talking to travelers." He has worked as a professional tour guide in Portland since 2023.
James Ross-Bright has been a storyteller for decades as a filmmaker and theater artist. He leads Peak Tours' highly specialized Forest Bathing experiences. His work blends horticulture, mindfulness, and environmental stewardship to foster a deeper connection with the natural world., combining thoughtful interpretation, engaging storytelling, and an appreciation for Oregon's natural environment. Behind the scenes, James also provides essential operational support, helping ensure Peak tours delivers organized, welcoming, and memorable experiences for every guest.
Our Offerings
We offer dynamic, guided sightseeing tours and reliable group transportation. Through local partnerships, we aim to enhance the overall visitor experience.
Our Mission
By providing captivating and educational tours that highlight the unique history and beauty of our region, we aim to inspire preservation and to foster cross-cultural appreciation.
Peak Tours is a Partner of Travel Portland, and a Member of the Portland Metro Chamber of Commerce, Oregon Outfitters and Guides Association, Willamette Valley Wineries Association. Our guides are Rose City Certified by the Portland Visitor Center.