It had been a few years since I ran this loop with my husband. Since then I had been on the Metacomet section, but the Timberlin section was not fresh in my mind. Luckily, it was pretty easy to follow. Although, this time, Laura and I decided to start a little north of Orchard Road because it was closer to drive to and made more sense to complete the more runnable section first. That worked out well as we enjoyed the first half knowing that this was supposed to be a relaxed FKT. Putting in enough effort to complete the loop in about 3 hours but not hurt oneself as Laura is preparing for the VT100. The trails in Timberlin are well maintained. But the section of trail next to the golf course road is over grown, so be prepared for that. It's also easy to miss how the blazes turn into the woods since you are on such a nice wide, quiet road. The climb up to Castle Craig is always such a slog but the views are great! We lucked out with a gorgeous day.
After crossing Rte 71 I noticed that the blue-blazes stopped matching up with my watch and I realized there must be a trail re-route. We followed the new blue-blazed section which takes you off the logging/ATV roads and on newly cut single track. It ends up being a little bit longer and less runnable but should get better as more people use it. I contacted the CFPA (who maintain the blue-blazes) and they confirmed the new route.
After popping out onto Orchard and crossing onto Kensington Road we missed the left had turn onto the trail, but instead ran all the way around on the road (adding some mileage). You can see on the map the way we went is definitely longer and hillier. I did not remember this section from the last time I was here plus the electrical pole on the street we parked at shows a blaze going up the road. So, watch out for that!
We each carried UltrAspire packs with 1.5 - 2 liters of water. That was the right about for the increasingly hot day. I believe we both ingested 1 GoMacro bar each and I had some UnTapped MapleAid.