Winter Ice Hiking Adventure
Step into a winter wonderland of frozen waterfalls, frosty caves, icicles and much more on this one-of-a-kind adventure.
the Roulette Story
Guided Hiking
Caves and Cracks Adventure
Explore the caves, cracks and crevasses created within the dissected plateau of the Catskills.
Waterfall and Valley Adventure
See why over 300 guests have enjoyed this classic adventure.
Abandoned Plane Crash Adventure
Hike and climb to panamoric mountaintop views – and the site of a plane crash.
Bachelor and Bachelorette Parties
Add some adventure to your bachelor or bachelorette plans.
Proposals & Engagements
Ask the big question in a place you will both remember forever.
Cliff Jumping Adventure
Enjoy an adrenaline cocktail with a jump from a 25 foot waterfall.
Corporate Events/Teambuilding
Bring the team closer together through an invigorating retreat day.
Sponsors
RHIP Packs
Click to learn more about the RHIP Modular Backpack system!
Kahtoola Microspikes
Completing my hikes in the winter would not have been possible without Kahtoola Microspikes.
Jackery USA
Jackery’s battery pack is the foundation of the power system for my van build.
Sunglass Warehouse
To read more about Sunglass Warehouse’s sponsorship of Roulette Travel, read our blog post here!
Recent News
Blackhead Mountain via Acra Point – Roulette Hike Review
Overview Blackhead Mountain is the 5th highest peak in the Catskill Mountains of Upstate New York, and its ascent via the northern side is one of the more difficult high peaks that I have come across. The lure of this…
Acra Point via Black Dome Range – Roulette Hike Review
Overview Sitting in the Northeast area of the Catskills Park, Acra Point is is a northeast-facing vista located along the famous escarpment trail – which takes you 25 miles from Windham to Haines Falls. For a taste of what the…
Giant Ledge and Panther Mountain – Roulette Hike Review
One of the most popular trails in the Catskills – for good reason. Combine an epic ledge traverse with a Catskill 35 in this winter adventure.
Monument Mountain, Massachusetts – Roulette Hike Review
Overview After taking clients through the Ice Glen Trail a few miles away, I passed by the trail sign for monument mountain. And, if I pass a sign for a mountain I was previously unaware of – I’m gonna stop.…
Here’s 10 Hidden Gems from Netflix and Amazon that I’ve Found during Quarantine
For me, its become almost a nightly ritual during these last two months to finish up my work (or nothing) for the day, and then start the search for something to watch. It feels like throwing darts sometimes – a…
Don’t ask a stranger to take a picture for you – use this trick instead
We’ve all been there at some point during our travels – you’re at a popular spot, or standing on the summit of a mountain, or perched at an epic view from a waterfall. You want to get a picture to…
