Every camper at Keewaydin gets to take a camping trip each month, either canoeing or hiking, depending on his interest and skills. The youngest boys go on trips that last two to four days, primarily in Vermont state parks and the Green Mountain National Forest. The middle age groups go on trips ranging from three to seven days in the tripping territories of the Adirondacks in New York and the lakes and rivers in New Hampshire and Maine. 

Moosalamoo, the wigwam for the oldest boys, is known as the "tripping wigwam."  "Moos" campers spend three or four weeks each summer on trips that take them to rugged territories of northern New England and remote rivers of Quebec, Canada. The most experienced campers go on a seventeen day canoe trip in the Verendrye Wildlife Preserve in Quebec.

The differences between departing and returning trippers highlight the importance of tripping to Keewaydin's mission. Campers leave Dunmore excited by  the challenges ahead--canoes to paddle, tents to pitch, fires to build, meals to  cook--and, despite wind, rain, or whatever else nature offered, they meet these challenges with their own hands and minds. Their obvious joy is partly from days of fun and adventure, but also from internal growth and maturation gained from the challenges of life on trip.

 While the entire experience of going away to camp engenders self-confidence, it is on these extended camping trips that boys gain a special sense of strength. They learn a lot about themselves. Above all, they learn to be both more  independent and self-reliant, on the one hand, and interdependent or group-oriented, on the other.  The camp’s motto of “Help the Other Fellow” is nevermore evident than on trip.

The Wilderness Trip

Boys aged sixteen and seventeen are eligible for Keewaydin's Wilderness Trip Program. In this program, boys come to camp for three days of trip preparation and training and then head north to Quebec, Canada for a four week adventure in native Cree territory. Most of the trip takes place on rivers and the trippers get to paddle through some exciting whitewater. On these trips boys get to see firsthand the unique Cree culture. Most, but not all, of the boys who go on this trip have been Keewaydin campers.

The Wilderness Trip has a leadership development component. Trippers may stay at camp upon their return for two days to work with the younger campers under the direction of a wigwam director. Combining this training component  with their tripping experience leads many wilderness trippers to become valued staff steeped in the ways of Keewaydin camping which they pass down to the next generation of campers.