High Road to Revenge is a flight-based combat game: during most of the game, the player controls an aircraft from a third-person perspective. It is an arcade flight game as opposed to a flight simulator; physics are relaxed, controls are simplified, and takeoffs and landings are completely automated. Project lead Jim Deal explained that Crimson Skies was built around an arcade design to make the game easy to learn, and to place its focus on action instead of the physics of flight. 
There are over twelve playable fighter aircraft in Crimson Skies: High Road to Revenge, including planes available to download over Xbox Live. Each aircraft has its own ratings for speed, maneuverability, armor, and a distinct weapons layout. Machine guns and cannons, which serve as primary weapons, have unlimited ammunition, but can temporarily overheat. Fighters are also equipped with limited-ammunition secondary weapons, examples of which include magnetic rockets, heavy cannons, and a Tesla coil. 
In keeping with the game's arcade nature, the armor and secondary ammunition of the player's aircraft can be replenished by flying into health and ammunition crates, which are dropped by destroyed enemies and scattered throughout the terrain. Developers also added special maneuvers, such as the barrel roll and the Immelmann, which the player can perform during flight through manipulation of the analog sticks. Use of these stunts is governed by a "special meter" which recharges over time during play. 
High Road to Revenge gives the player the ability to switch out of their current plane during gameplay and commandeer additional aircraft on the ground. The player also has the ability to take control of fixed weapon emplacements, at which time the camera shifts to a first-person view. Turret types include machine guns, flak cannons and rocket launchers. They are found in most of the game's maps, built into the terrain or mounted on vehicles such as Zeppelins.