MAINE TRAIL FINDER: "Pleasant Mountain is southern Maine’s tallest mountain at 2,006 feet. The nearly ten mile trail network offers a variety of moderately challenging day hikes. The summits provide commanding views of the White Mountains to the west and spectacular views to the east."
There are 4 main trails that lead up Pleasant Mountain. Ledges Trail, Bald Peak Trail, Fire Warden's Trail, and Southwest Ridge Trail. There are also two secondary trails, Sue's Way and North Ridge Trail, that create a loop that connects to the summit of Shawnee Peak Ski Area to the north. Each of the 4 main trailheads has a small roofed information board. (Southwest Ridge Trail has a trail sign with the information attached.)
Start at any trailhead information board, then run up and down every trail touching the information board at the other three trailheads, and finishing back wherever you started. The only variation is on the Bald Peak Trail where you can choose to run the top portion of it, or Sue's Way and North Ridge Trail in one direction, and take the other route on your return. There is a short trail to a rock formation called "Needle's Eye" off the Bald Peak Trail that is not included because it doesn't have a defined turn around. There is also a small unnamed trail that leads to Shawnee Peak Ski Area that is not include for the same reason. The total route is roughly 18 miles long with a little under 7,000' of elevation gain.
I made an attempt at this FKT on June 23, 2018. At the time I was going for Jesse Veinotte's time. I started from Southwest Trail, did Ledges Trail next, down Sue's Way, up Bald Peak Trail, did Firewarden's Trail and finished back at Southwest Trail. My strategy was to start and finish on the more runnable trails. I felt real good for the first half of the run, but I crashed going up Bald Peak and struggled to keep up my pace near the end. My final time was 04:49:53 (https://www.strava.com/activities/1657095009/overview) and felt very accomplished with it. When you stop and think about it, it's nearly the distance and elevation of a Presi Traverse. I would like to give another shot some day, but 4:10:16 might be out of range for me. Congrats Brian!