You'll find the opportunity for this achievement later in the game during the second mission of the Eastern Winds campaign; 'All Aboard'.
You should try for all the medals at once in this mission. Set the difficulty to easy and choose the lightly armed I-16. You'll have to destroy all enemy vehicles and complete the secondary objectives as well as destroying the train.
At the start; speed boost towards the marker, it'll disappear but keep going until you find the '5' vehicles with some buildings, be sure to destroy them all, then move to the next marker.
On your way to the next marker you'll spot a convoy of '6' vehicles to your right, be sure to divert and destroy them all before approaching the marker.
Destroy the next '5' vehicles and a couple of buildings then onto the next marker. Before you reach the next marker you'll be given a secondary objective to destroy '3' Romanian fighters, be sure to engage and destroy them all.
At the next marker destroy the '5' vehicles and you'll get the cutscene with the train. Speed boost towards the train and aim for the front engine, destroy it all as quickly as possible and the train will stop, the achievement will not pop however until all parts of it are destroyed.
When the train is done you'll find '4' tanks marked as yellow targets near the pipes, be sure to destroy them all before taking out the '5' Messerschmitts at the end.