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You'll likely need a rest after the events of the Red Dead Redemption mission "New Friends, Old Problems" (even if you don't, you'll have to wait for morning for the next mission to become available). In the morning, make your way back to the ranch house to meet Bonnie for your next task. You are also free to roam around a bit for the first time, so feel free to check out the countryside, maybe hunt a bit and sell your goods at the general store.
When you're ready, walk into the yellow "X" on the porch to get started.
Inside the house, you'll come upon Bonnie as she's walking up the stairs. She'll invite you in and, after a bit of evasive conversation, she'll challenge you to a horse race.
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Racing Around the Ranch
The race course will take you through the ranch and into the surrounding hills. The course is marked by smoking campfires, and you will need to keep your next waypoint in mind constantly if you want to win the race.
The key here is to urge your horse to move as quickly as possible without exhausting it. The blue bar to the right of your mini map is your horse's stamina. You can press the "A" or "X" button to use your spurs and urge your horse to move faster, but don't overdo it or you'll find yourself on the ground. The key is to establish a rhythm, spurring regularly but not depleting the stamina of your horse too quickly. Let it recover a bit before you spur it again.
If the stamina gauge goes into the red, you need to back off or your horse will buck you off. You can win this race fairly easily as long as you maintain a good speed, so don't worry too much about sprinting all the time. Better to play it safe and stay on your horse.
Keep your speed up by staying on the path, running cross country will slow you down, so only do so when there is a clear advantage to be gained by it.
The race ends back at the ranch, so don't be afraid to sprint to the finish when you hit the gates.
Win or lose, the mission is completed. Winning will earn you a bit more fame, however.
After the race, Bonnie suggests you might want to pay the local Marshal a visit. You now have two contacts from which to take missions, but we're not quite done with Miss MacFarlane just yet.
For more mission walkthroughs, cheat codes, weapons guides, and more, check out our Ultimate Guide to Red Dead Redemption.