On the Trail is a head-to-head race game that puts players in the role of endurance runners tackling a demanding trail made up of colored race legs and tactical stops. The theme centers on pacing, stamina, and smart decision-making as runners push toward the final aid station while coping with physical setbacks and seizing moments of momentum.
Each turn, players must advance their runner by completing at least one leg of the trail, playing Race cards that match the color of the next leg, using wild cards, or spending pairs of cards as substitutes. Players choose how far to push each turn, deciding when to stop, which affects both hand management and the type of stop they land on. Aid Stations can provide reusable Boost cards with special abilities, while Setback stops impose ongoing penalties that restrict options and compound over time. After movement, players refresh their hand, but poor planning or bad luck can make it impossible to move, forcing a runner to drop out of the race.
The goal is to be the first to reach the final Aid Station and qualify as a finisher. Once a player finishes, the round is completed so both players have taken the same number of turns. If only one player finishes, they win immediately; if both finish, the runner with the most cards left in hand claims victory, rewarding careful timing and restraint. If a player cannot advance on their turn, they suffer a DNF, leaving their opponent with a clear path to victory if they can still complete the race.