Welcome
Just minutes from Trenton and Chattanooga, the Lookout Pickleball Club Stay & Play retreat offers four alpine style cabins with sunset views and exclusive access to two covered, lighted pickleball courts. Locally owned on Lookout Mountain, it’s the perfect getaway where mountain relaxation meets America’s fasted growing sport.
Who we are
About Us
Matt Siver and Jake Armstrong have been friends for over 35 years, sharing a lifelong passion for creativity, adventure and building meaningful experiences. After years of talking about starting a business together, the dream became reality when Matt and family moved to the area and Jake purchased land on Lookout Mountain.
The idea for the Lookout Pickleball Club grew naturally — combining their love for the outdoors, design and community into something truly unique. What started as a shared vision has become a place where people can relax, play and reconnect with what matters most.
This project is the culmination of decades of friendship, planning, and finding the perfect setting to bring something special to the region. Matt and Jake plan to continue developing new experiences and hope every guest finds a bit of sanctuary, inspiration and joy during their stay at the Lookout Pickleball Club Stay & Play Mountain Retreat.