This year we did something called “Hill Climb Mondays”.
We live on a bench on the mountain and have several long streets that are parallel to each other. We all climb the hill to the top, then the rider that reaches the top first comes down, and we all latch on to him as he comes down. Then we move to the next street and repeat. Each hill climb is a mini-race.
We do about 7 climbs that last from 2 to 5 minutes. It creates a great training ride for all levels, while creating some competitiveness between similar levels. We usually just get from 3 to 7 people. More people is definitely better.
I've done "Indian Runs" with groups of riders with varying fitness levels. All riders stay together during the warmup. On the climbs, tell the more fit riders to hammer up at their pace. Once they reach the top, they come back down and rejoin the group. They can either repeat the process until everyone reaches the top, or just stick with the main group until everyone reaches the top.
Any rider that feels like they can handle the faster pace can join the more advance riders during one of the Indian Runs. If they start to run out of steam, they can always either slow it down and finish the climb, or come back to the main group and finish the climb with them.
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