The Webb Schools are situated in an ideal location, ten minutes from Mt. Baldy, ninety minutes from the Pacific Ocean, and two hours from numerous national parks, forests and recreation areas. Rock climbing in Joshua Tree, mountain biking in Big Bear, hiking San Gorgonio, skiing at Mt. High, and sea kayaking in Laguna Beach are an easy drive away. It's not unusual to be in the snow one weekend, and at the beach the next. Webb's Outdoor Program is a testament to the school's founding values, and to the spirit of today's student body. The Outdoor Program at Webb is dedicated to developing leadership through outdoor experience.

In 2010-11, over 150 students voluntarily participated in some sort of outdoor trip, whether that was snorkeling, snow-camping, or hiking to the bottom of the Grand Canyon. Overall, the school offered over twenty-five outdoor trips during the course of the school year, ranging from simple day trips to four-day overnights. Webb also practices environmental stewardship, having adopted the Bear Flats trail on Mt. Baldy for routine maintenance. You can read about all of our adventures, and see pictures, on Happy Trails, a blog dedicated to the Webb Outdoor Program.