Upstate Hiking and Brian Afflixio began guiding clients in Upstate New York in 2018, after taking numerous friends, family members, and strangers (who would become friends) from the internet hiking. Brian spent years finding the best routes, views and features of both the Catskills and Adirondacks – while honing in on his photography so that he could help others safely adventure through the wilderness.
After seeing how so many people focus on taking phone photos throughout a trip or adventure – we found that providing candid, action and some posed photo opportunities throughout the hike helps hikers unplug and immerse themselves in the wilderness without the distraction of the outside world.
Since 2018, Brian, Cliff and Joe have led thousands of hikers safely through the trails of the Catskills, Adirondacks and Shawangunks.
Upstate Hiking a DBA of Roulette Travel Adventures and Media, LLC, was founded and currently operated by owner and lead guide, Brian Afflixio.

Brian Afflixio
Founder & Lead Guide
Brian is the owner and founder of Upstate Hiking, and has been working as a guide in the Catskills since 2018 after leaving the corporate software world. As an avid photographer, Brian both guides and photographs guests on a wide variety of hiking adventures. When not guiding, Brian spends time traveling in his campervan with his dog, Kody, visiting National Parks, and checking countries off the bucket list.
Specializing in –
- Northeastern Catskills & Adirondacks
- Waterfall hikes
- Adventure photography
- Ice hiking

Cliff Goldstein
Licensed Guide
Cliff is a licensed hiking, boating & camping guide. He has explored and adventured extensively throughout the Western US, Northeast and across Latin America. After spending most of his early life in the SF Bay Area, he met his wife, Dani, while living as a digital nomad in Puerto Rico, and they have now settled in the Hudson Valley, along with their ridiculously cute goldendoodle, Pancho.
Specializing in –
- Hudson Valley, Southern Catskills, Shawangunks
- Longer distance hikes
- Corporate team building
- Dog-friendly routes

Joe Chenier
Licensed Guide
Joe Chenier has been guiding hikes across the Catskills for several years after hiking the Catskill 3500s multiple times and assisting with an on trail rescue in 2021. Joe is also a civil engineer by day, and enjoys skiing, kayaking, camping and spending time with his family when not guiding. Whether you’re looking to conquer the Catskills 35 challenge, or tackle one of the many bushwhacks – Joe’s your guide!
Specializing in –
- Mid-Catskills, Hudson Valley, Catskill High Peaks
- Catskill 35’er hikes
- Bushwhacking
