I had prepped all the envelopes and written out instructions and driving directions ahead of time. To make everything look really professional, I adapted free printables I found online. Here's what I used. I changed the envelopes to say "birthday" instead of "date," because it would have been creepy otherwise.
His first challenge was a Detour (a choice between two tasks): Shape Up or Ship Out. For Shape Up, he would have to complete the minimum requirements to join the fire department. He'd have to do sit-ups and push-ups, monitored by the fire chief (The Brother). For Ship Out, he'd need to take out our kayak and use an improvised paddle to cross the river, retrieve a leaf, and return to the other side.
He chose to Ship Out.
He fell down the bank at one point, and I thought the race had ended prematurely with a trip to the emergency room, but he was okay. Thankfully.
When he returned with his leaf, he received a Roadblock called Shall I Compare Thee to a Summer's Day. Dad had to write a sonnet (following the official structure of a sonnet--no cheating allowed), directed to his lady love (Mum). If she liked it, she would give him his next clue. If she hated it, she could spurn him and send him back for a rewrite.
Then we sent him to the library for Dewey or Don't We?, a test of his library skills. Dad needs to work on his library skills.
He had to assemble a card from pieces of paper found in books I'd picked out. They all were about things that had happened during Dad's life, or about topics he found interesting, about being aged, that sort of thing.
When he put them all together, he had a quote and another Roadblock, We Like You a Latte.
Dad memorized the quote and walked to Modoc's Market, where the management had kindly agreed to work with me. Dad would walk in, repeat the quote, and receive a latte. I'd prepaid for the drink and left a card with Dad's picture and a copy of the quote. Dad was so speedy, Mum and Paul missed this and I didn't get any video!
We took pictures on Modoc's elephant statue when we finished.
Then, Dad got more route info, which took him to dinner at The Rusty Dog in Huntington. That was the pit-stop for this leg of the race (although not really, because we let him come home to sleep and didn't leave him to fend for himself in Huntington).