We did Chilly Hilly 3 times way back when we first started riding (before recumbents) - always enjoyed it. We would drive up from Portland on Saturday morning, getting a room at the Best Western two blocks from the ferry terminal. Hung out downtown Seattle for the day, good dinner within walking of hotel. Checked out before heading out for the ride. The hotel let us leave the car in their parking garage for the day (driving back to Portland after the ride). Would catch the first ferry that is bikes only - no cars.
On the island, I would wait a few minutes before starting my ride. Let the majority of the riders get out ahead of me. I was always (and still am) one of the slowest uphill riders around. I didn't want to be in front of everyone just to have them all try to pass me. Yes Virginia, 2.5 mph really is a speed and I don't fall over! You start your first climb within a couple blocks of the ferry. Food at the rest stops is good and I remember there being some private stands set up in driveways, selling hot chocolate, baked cookies, brownies, Gatorade, etc.
By being slow, the crowds all pulled away from me and I had a very pleasant, quiet ride, enjoying the views and sounds. Could tell when the next ferry had arrived and the next wave of riders passed me. Then got quiet again. I always just rode the 18 mile loop while DH did the 36 mile. We ended up back at the ferry within 10 minutes of each other.
Might be good to do this ride again, now that I am a stronger, better rider. See how the bents handle it. Though I do still climb slowly, just at 4-5mph now instead of 2.5 :-)
Have fun and I hope you have clear weather. The views are awesome!
Edna



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