Over half of Pine Island's camping trips are backpacking trips, and most are designed to summit one or several mountains in Maine or New Hampshire. Younger boys camp at the base of mountains like Saddleback or Mt. Washington and day hike to the summit without packs. Older boys carry their packs from campsite to campsite, on routes that take them over summits and along ridges above the tree line.
A typical summer includes the following hiking trips, among others:
Bald Pate - three-day hike on the Appalachian Trail for beginning hikers.
Saddleback - three-day hike on Saddleback Mountain for beginning hikers. Campers spend the night at Piazza Rock campground on the Appalachian Trail.
Bigelow - three-day hike on Mt. Bigelow. Campers hike over the mountain with packs and end at Flagstaff Lake. For beginning hikers.
Mt. Washington - three-day hike up Mt. Washington for beginning hikers.
Carter-Moriah - four-day hike in the White Mountains for intermediate hikers.
Northern Peaks - four-day hiking trip on the Appalachian Trail following the Presidential Peaks north of Mt. Washington. For intermediate hikers.
Flag Big Flag - four-day adventure in the War Yacht, a 28-foot canoe that can be paddled or sailed. Campers paddle on Flagstaff Lake to the base of Mt. Bigelow. They ascend Mt. Bigelow, spending one night on the mountain, and then paddle back the length of Flagstaff Lake. This trip is for intermediate paddlers/hikers.
Maine Peaks - five-day hike following the Appalachian Trail from Saddleback to Sugarloaf. For advanced hikers.
Junior Katahdin - three-day hike for intermediate hikers who ascend Mt. Katahdin without packs.
Senior Katahdin - five-day hike for advanced hikers on Maine's tallest mountain.
Senior Whites - seven-day trip from Franconia Notch to Pinkham Notch. Campers summit Mt. Lafeyette, Webster, and the Presidentials. For advanced hikers.
Cliffhanger - four-day trip in the White Mountains from Ethan Pond to the Kangamangus Highway including Mt. Guyot and Mt. Bond. For intermediate hikers.
Old Speck - four-day hike following the Appalachian Trail through Mahoosuc Notch in New Hampshire and Maine. For advanced hikers.
Lafayette's March - five-day hiking trip in the White Mountains with packs. For intermediate hikers.