The forecast predicted this to be the coolest day of the week, so I decided on Monday that I would do this on Tuesday. My partner agreed to provide me with a shuttle service from the finish to the start so I could leave my car and get myself home when I finished. I stashed water and snacks at around the 20 mile mark near the Iron Mine Lane trailhead, which turned out to be perfect.
I set out on the East Branch at ~9:15 am on Tuesday, July 7th carrying 3 L of water and lots of food. It was mostly overcast all day, though the sun peaked out a few times to heat things up, and I spent the entire day soaked in sweat. The sweat was good because it meant I was hydrating well, but it kept washing off my bug repellant, which is not ideal at the height of deer fly season. I reapplied bug repellant at least 1x per hour. I ran out of water ~1.5 miles from my stash. I couldn't have planned that better! From the water stop on, the climbs became relentless. However, the scenery made up for the suffering. Yale Forest is a magical place. When I finally arrived at Bigelow Hollow, I made my final push towards the finish.
If I were to do this again, I'd do it in early spring when the plants are still somewhat dormant because I couldn't see a lot of the trail along the pond to the finish, and that made for slow going at the end. In all, this trail is awesome. If you can't get out to do it all at once, go do it in sections because it's totally worth it.
The worst part? You finish in the middle of nowhere at the MA/CT border, and it's a 3 mile walk back to the parking lot. I parked at the Fisherman's lot, which is furthest, because I didn't want to risk getting locked in the park if it took me longer than planned. There are closer parking areas, but you will still have to walk 2-2.5 miles.