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Cheyenne Chaffee

Cheyenne Chaffee

Cheyenne calls New Hampshire home but ventures West in the spring through autumn to seek lower humidity and less bugs. He has guided in the Black Hills for the past 11 years and considers the Needles one of his second homes. When not working at Sylvan he spends time guiding in other areas across the country such as the Tetons, Wind Rivers and New England in the winter for ice season.

Cheyenne has an Associate Degree in Outdoor Recreation Leadership from Colorado Mountain College where he has also been instructing the classes he took as a student for the last 13 years.

When not guiding he can often be found partaking in a plethora of shenanigans such as but not limited to throwing tomahawks, playing guitar, listening to metal, mountain biking, and the occasional quiet canoe ride.


AMGA Certified Rock Guide
AMGA Assistant Alpine Guide
AMGA Assistant SPI Provider
Wilderness First Responder

5 stars

My boyfriend and I booked a 6 hour session with Shankar, and had a fantastic time! We both have indoor climbing experience, him some outdoor climbing experience, and we were afraid that we wouldn't find climbs that were "just right" for us. Shankar did an excellent job picking climbs for us, he made it fun, and we felt super safe the entire time. I highly recommend booking with him at Sylvan Rocks!


5 stars

My family took Sylvan's beginning rock climbing class and I would recommend it 100%! We have an 11 and 14 year old and my husband and I felt assured that safety was Sylvan's priority. Our instructor, Ryan did a terrific job explaining techniques at an understandable pace and was very patient. He made sure we mastered each progression before moving on so we didn't feel rushed into the next level. We were all confidently climbing 50 feet by the end of our class. You couldn't ask for a more picturesque, safe, well-organized, and fun experience for the whole family. Thanks, Ryan and Sylvan Climbing School!


5 stars

Brandon and Jeff were phenomenal guides. I was with Jeff for day two in Custer and Summit Day on Devils Tower. He was knowledgeable, patient, encouraging, and enhanced the experience. Safety was their priority number 1 and I did not feel unsafe at any given point. I would highly recommend Sylvan Rocks Climbing School to anyone looking to climb in the Black Hills.


American Mountain Guides Association

The Highest Standards

Accredited by the American Mountain Guides Association

As the only AMGA Accredited Guide Service in the area, we are committed to a high standard of climbing professionalism. The AMGA is an internationally recognized association offering courses, exams and certifications designed to certify guides and instructors as well as accredit businesses.

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Our Friends

  • South Dakota Outdoor Shop
  • Black Hills Basecamp
  • Custer Chamber of Commerce
  • Granite Sports
  • Black Hills Climbers Coalition

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