Street races are available after talking to an associate, Robert Topping, in Sequence 3. Look at the map and look for the double-flag icon, the same as the one on the achievement tile. There are three kinds of street races and only two of them count towards this achievement.
1. Lap Races
Jacob / Evie needs to come first against three opponents in a multi-lap race.
2. A to B Races
Jacob / Evie needs to come first against three opponents, passing through all checkpoints along the way.
The one which does not count is the Exotic Races, which are Jacob / Evie alone racing against the train.
Jacob and Evie always start at the back and their carriages have the same speed as the opponents. Opponents occassionally make mistakes and these are the only time to overtake them. However, when successfully taking the lead, the game mechanics allow the opponents to gain a temporary speed boost to close up quickly from behind, so there is not much room for errors.
Jacob and Evie can acquire the following skills to increase their driving capabilities:
1. Driver I (Level 3, 2 skill points required)
Collisions inflict less damage and don't slow you down as much while driving.
2. Driver II (Level 5, 4 skill points required)
Carriages you drive accelerate significantly faster.
Maintaining maximum speed is crucial; always pressing A to boost speed is recommended, and ramming opponents should only be done as a last resort. If you successfully take the lead, always use the mini-map and block any opponents who attempt to take over.