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@cynddl
Alright, I've been asked for a hill, here is my hill: https://www.strava.com/segments/23800172. Freshly baked segment from this morning. I tried a couple of different routes to the summit and hope I've found a good balance of difficulty, secluded roads, and steepness. 76m of elevation, avg grade 6% with a few steep parts up to 15-18%.
The segment is made of two sections, first on the road (King's Head Rd, a little busy, then Pole Hill Rd, the beefy part, very secluded), easily doable with a hardcore fixie; THEN, you don't step down, and keep going: there's a nice trail with a bit more difficulty but not that much. I tried with a 50x17 and it was too much for the end of the trail, I had to walk the last meters. 46x18 should typically be a breeze to the summit.
Although I'm not the RuleMaster @Lucybee, I'd suggest we select the winner with the highest gear up to the Obelisk, and if no one does it without putting a foot down, we restrict up to the end of Pole Hill Rd?
P.S. You'll find beautiful views up there and on the neighboring hills, go during the day.