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- Section I – the section between the river and Whitney Avenue (Route 10) is mostly flat with one up and down.
- Section II – as you leave the Red Diamond, the Blue is up a very steep rise with much loose dirt. This is ‘the dumpling’. The top of the Dumpling is flat and then you have a steep and very tricky drop. Going the other way does not decrease the difficulty. Going up the steep rocky ‘cliff’ is tough, but doing down towards the Diamond is very tricky, as the slope is deep and the dirt loose. It is possibly the most difficult part of the trail.
- Section II continues then up the back of the Head, steep and daunting seeming, it’s really not as bad as it looks. Just be careful. Coming down the back of the Head is steep and tricky, once down onto the slope, it’s relatively easy going.
- Sections III, IV, V, and most of VI are rocky, tricky, steep – sections very doable, but done with caution. Once you come off Hezekiah’s Knob, the path is relatively challenge free.
- Section VII has some ups and downs, but not really tricky. At the end the trail goes down to Hartford Turnpike and if your plans are to do a turn-around, the trail back up the slope is a steep climb, but not rocky or tricky.