This hike starts from the Lake Sebago parking lot.  From the parking lot, cross Seven Lakes Drive to access the trailhead and Seven Hills Trail (blue markers).  The start is a steep climb traversing to the top of Conklin Mountain for .35 miles until you descend to Diamond Creek.  Cross the creek and continue up a short way where the Seven Hills Trail makes a sharp right turn off the woods road you have been on. The woods road continues straight and many people miss the turn off because it is not well marked.

A half mile after Diamond Creek, the Seven Hills trail intersects with the Tuxedo-Mt. Ivy trail (red markers).  Continue on the Seven Hills trail and soon you will gain the Diamond Mountain ridge.  This ridge is over one mile long and has great view point looking northwest.  After one the trail descends steeply along a rock cliff requiring some down climbing.  Turn back here or continue to descend and create a small lollipop loop hike.

Once down from the cliff, the trail meets the Kakiat Trail (white markers).  Turn left and hike about 100 yards until you come to a bridge crossing Pine Meadow Brook.  The Kakiat Trail crosses the bridge so stay straight where to gain the Pine Meadow Trail.  The Pine Meadow Trail follows the brook passing some nice cascades.  Follow for a half mile to some  stone ruins.  Pass the ruins on the left, do not drop down onto a woods road that is nearby.  The Pine Meadow trail will make a sharp right just after the ruins at the intersection of two yellow trails.  The Yellow trail straight ahead is the Diamond Mountain Tower Trail (there is no tower on this trail).  You will know you are on the correct trail if the ascent is no so steep.  Follow for a half mile until you reach the ridge of Diamond Mountain and the Seven Hills Trail.  Turn right and follow back the way you came.