We measure the state dynamics of a tunable anharmonic quantum system, the Josephson phase circuit, under the excitation of a frequency-chirped drive. At small anharmonicity, the state evolves like a wavepacket -a characteristic response in classical oscillators; in this regime we report exponentially enhanced lifetimes of highly excited states, held by the drive. At large anharmonicity, we observe sharp steps, corresponding to the excitation of discrete energy levels. The continuous transition between the two regimes is mapped by measuring the threshold of these two effects.Ever since the laws of quantum mechanics were formulated, there has been an ongoing effort to explain the emergence of classical laws in experimental systems. The first explanation by Bohr states that these systems operate in the limit of large quantum numbers [1], in which case they may be described by a wavepacket that on the average follows the classical equations of motion [2]. In addition, coupling to uncontrolled, external degrees of freedom (decoherence), is often related to the emergence of classicality [3]. Recent experiments and calculations have demonstrated the quantum to classical transition in oscillators, via noise saturation at low temperature due to zero point fluctuations [4, 5], and harmonic behavior at high temperatures in a cavity-QED system [6].In a classical anharmonic oscillator, such as a pendulum, the energy expectation can be deterministically increased to large values if the driving force is frequencychirped and its amplitude is sufficiently large. This phenomenon is commonly known as autoresonance [7]. The physical mechanism behind this effect is adiabatic, nonlinear phase-locking between the system and the drive, yielding a controllable excitation as the system's resonance frequency follows the drive frequency as a function of time. This effect is utilized in a wide variety of systems [8, 9], and recently in Josephson-based oscillators [5, 10]. In a quantum anharmonic oscillator, the expected time evolution under a similar drive is sequential excitation of single energy levels of the system, or "quantum ladder climbing" [11]. In practice, for a given anharmonicity the drive itself introduces some mixing between the energy levels due to power broadening and finite bandwidth, which may wash out ladder climbing and lead to a classical behavior in a quantum system [12,13]. In this letter, we measure the dynamics in these two distinct regimes in the same system by varying the drive parameters and the system's anharmonicity.Our system, the Josephson phase circuit (JPC, see Fig. 1a), is a superconducting oscillator with a nonlinear inductor formed by a Josephson junction. It can be described energetically by a double-well potential that depends on the phase difference δ across the junction. We tune the potential by means of an external magnetic flux bias [14] to vary the anharmonicity and measure the state. Traditionally, the circuit is operated as a twolevel system (qubit) [14,15], or a d-level system (qudit) [16], by ...