I ran/hiked a self-supported route on Mount Monadnock (Jaffrey, NH) on 6/1/14 that crossed the summit three times. Total elapsed time was 5:57:46. Here are two representations of the route:
I cached water at the Marlboro Trail, Dublin Trail and Pumpelly Trail trailheads with the intention of starting on the White Dot Trail at the state park and making a four summit "star" route. However, when I got to the park entrance, it was closed because the lot was full. The gorgeous day and my late start foiled me! I adjusted my plans and headed for the closest trailhead, the Marlboro Trail. I figured I would start there and include the White Dot as the final leg of the route. I also thought I could refill my water at park HQ before the final ascent back to the summit. That would have changed my route from self-supported to supported.
I started my timer at the trailhead kiosk at the Marlboro Trail and ended it there as well. In the end, I bailed on the White Dot leg due to physical and mental tiredness, so I submit the revised route as the FKT. I would love to see someone complete the full route, but it may be a while before I attempt it!
Starting and finishing on the Marlboro Trail was tough because large portions of it were unrunnable for me. The Dublin Trail is slightly better but still difficult. The Pumpelly Trail has the most runnable sections, primarily the upper 1/3 and lower 1/3 of the trail. It's also tricky to locate the exact route of the Pumpelly when descending from the summit, but easier on the way back up. In general, keep a heading to the NE while descending and follow the cairns from there. The Marlboro and Dublin trails merge before ascending the summit, and I followed the joint trail up to and down from the summit instead of cutting across from one to the other.
If you attempt this route, it will help to do it on a less-than-perfect, yet dry, day. There are many chokepoints in the steep sections on the trails where I had to wait for others to pass.
I would love to see someone else get out there and lower this time, as I expect there is plenty of room to do so! For some real craziness, try the 4-summit version with White Dot, 5-summit version with White Dot and White Arrow or a 6-summit version with White Dot, White Arrow and Pumpelly/Red Spot/Birchtoft.