On June 16, 1999, approximately 0835 mountain daylight time, a Mooney M20E, N9355M, registered to and operated by the pilot, was destroyed when it collided with terrain during climb shortly after takeoff from Fremont County Airport, Canon City, Colorado. The instrument-rated commercial pilot and instrument-rated commercial certificated passenger received minor injuries. No flight plan was filed for the personal cross-country flight being operated under Title 14 CFR Part 91 with an intended destination of Rifle, Colorado. Instrument meteorological conditions prevailed in the accident area. According to the pilot, he departed Canon City and climbed to 1,000 feet above ground level (agl). He followed the Arkansas River upstream to the west and "determined there was not a VFR departure in that area." He followed the river back east, and then headed towards the southeast paralleling the east side of the mountains. Shortly after turning, "it appeared that there was an opportunity for a VFR climb." He initiated a climb, and soon thereafter entered the clouds. He continued in a climb while in instrument conditions, and attempted to use the airplane's Global Positioning System (GPS) to either return to Canon City or divert to Pueblo, Colorado. Shortly after initiating the climb, the aircraft impacted upsloping, mountainous terrain at an elevation of 8,500 feet on an approximate heading of 210 degrees. The wings were sheared off during the impact sequence, the fuselage was crushed and broken into several sections, and the tail was bent 90 degrees to the left. According to Denver Automated Flight Service Station (AFSS) records, no weather briefing was obtained under the registration of N9355M. However, according to the pilot, he obtained a weather briefing using another aircraft registration of N303MD. AFSS records confirmed that a weather briefing was obtained under that aircraft registration number, and the briefer advised the pilot during that briefing that VFR flight was not recommended. At 0754, weather conditions at Pueblo, located 35 miles east of the accident site, were reported as overcast ceilings at 3,400 feet agl. At 0854, overcast ceilings were reported at 3,600 feet agl. According to a pilot who was performing a GPS approach into Fremont County near the time of the accident, the ceilings were approximately 600 feet overcast at the airport.