<< Back to Robb Report, August 2014

Shades of Gray

  • Scott Armstrong

Gray & Co.’s personalized trips take cyclists on the rides of their lives.

After a morning of pedaling on the back roads of the Texas Hill Country, I was hungry, parched, and—even on a crisp December day—hot from the searing sun. My 29-mile journey had taken me through pin-sized hamlets, past lavender farms, and over rugged limestone hills. The ride concluded in the pastoral outskirts of Austin, where relief came in the form of protein (a rack of ribs and a hearty pile of brisket), carbohydrates (potato salad), and plenty of hydration (Lone Star beer) at a barbecue joint called Cranky Frank’s. 

Designed around my passions for cycling, barbecue, and even World War II history, my Texas adventure had come at the suggestion of Cari Gray, owner of the Toronto-based adventure-travel outfitter Gray & Co. Launched in 2009, Gray’s company offers bespoke cycling and hiking itineraries across the globe, focusing on less-traveled—though no less spectacular—destinations for the pursuits. Gray, who spent nearly 20 years working for the outfitter Butterfield & Robinson, sends clients everywhere from the Texas Hill Country and California’s Santa Ynez Valley to Chile, Colombia, Myanmar, New Zealand, and South Africa. “It has a direct correlation to the roads,” Gray says. “I recommend places with the best pavement and the least traffic.”

Each Gray & Co. journey (priced from roughly $1,500 per person, per day) is custom designed, with no set calendar of departures, no catalogs, and no group trips with strangers. Itineraries are born out of personal interviews conducted by Gray, allowing her to weave clients’ passions—from bird-watching and fishing to whiskey and wine—into each day’s activities. Each guide leads no more than three riders at a time, and additional guides are dispatched in advance to guarantee that road conditions are up to standards. “We work in the present and the future,” Gray says. “While guides ensure guests are having a great lunch, others are scouting the next day’s route. There is no margin for error.”

Before my arrival in the Hill Country, Gray provided me with a detailed itinerary highlighting options for daily rides, accommodations, and dining, as well as must-see stops along the way. The four-day itinerary culminated in a more than 50-mile ride wheeling past cattle ranches, enormous pink-granite rock formations, and a 100-year-old church. Knowing my penchant for small-batch bourbon, Gray also arranged a private tour and tasting at Garrison Brothers Distillery, an award-winning whiskey maker in the sleepy town of Hye. But my greatest thrill came just after my brisket lunch at Cranky Frank’s: a surprise visit to the National Museum of the Pacific War, a Hill Country high point for any history buff.  

Gray & Co., 416.998.4082, www.grayandco.ca