Pilot Richard Lewis, 76, and passenger Tony Cook, 79, two well-known members of East Yorkshire's farming community and neighbours in Burton Pidsea in Holderness, both died in the crash.
A report by the Air Accidents Investigations Branch said the pair's departure from Midlem Airport was delayed for a fault to be repaired and as a result they did not get back to Beverley Airfield until after dark on October 10, 2018.
Mr Lewis, who until 2017 was part-owner of the airfield, called a club member friend and asked him to drive to the airstrip and shine his car headlights on the runway.
The club member saw the Reims Cessna F172N Skyhawk circling to the west of the airfield when it "suddenly descended vertically and disappeared from his view" around 6.25pm.
Feeling certain it had crashed he called the emergency services as well as other members of the club, who started looking for the aircraft, which was eventually found in a small copse at Wilfholme, just over a mile from the airfield, more than four hours later.
But both men had been fatally injured on impact.
The report said the pilot, who had held a private pilot's licence for 25 years, did not have a night rating and no night flying time had been recorded in his logbook.
The report stated: "There was no evidence that he had ever flown at night before."
Flying in the darkness would have been an "unfamiliar and demanding task", it said.
There was enough fuel to have diverted to Humberside Airport 20 nautical miles away - but that may have appeared a "daunting prospect" as the airport had become a busy international hub since he last flew there in 1995.
"These factors may have made Humberside appear to be a more difficult option than landing at Beverley, where he was very familiar with the airfield," it added.
The report concluded that it was likely that "the pilot became disorientated when in a descending turn near the final approach and allowed the nose to pitch down too steeply."