The most common time to file a flight plan is after receiving your weather briefing. When the briefer is finished talking, simply state that you would like to file a VFR flight plan. The briefer will help you if you are unsure of the format, but it's a good idea to have a flight planning form handy.
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So, as a general answer, in the U.S., flight at altitudes at and above 18,000 feet (5.49 km) above mean sea level requires a flight plan (an Instrument Flight Rules flight plan - known as IFR) and joyriding/offroading as you put it, is not permitted.
DVFR (Defense VFR)In the increased environment of national security that exists today, flight plans are required before penetrating or flying in Air Defense Identification Zones (ADIZ). Expanded information can be found in FAR Part 99, Security Control of Air Traffic.
(a) No person may take off an aircraft unless the pilot in command has filed a flight plan, containing the appropriate information required by part 91, with the nearest FAA communication station or appropriate military station or, when operating outside the United States, with other appropriate authority.
Flight Plan RequirementsAll IFR flights require a flight plan submitted to an FAA facility or facilities as described in the U.S. Aeronautical Information Publication ( AIP ), Sections ENR 1.10 and ENR 1.11 and in the Aeronautical Information Manual ( AIM ), Section 5-1-6.
14 CFR § 91.103, Preflight Action directs pilots to become familiar with all available information concerning a planned flight prior to departure, including NOTAMs. Pilots may change their flight plan based on available information. Current NOTAM information may affect: Aerodromes.
You can “air file,” or file an IFR flight plan while en route. Ideally, this would involve calling up the nearest ATC frequency, stating your N number, and waiting for a controller to acknowledge your transmission.
In the United States, a pilot is required to log all flight time that is used to meet the minimum requirements for a certificate, rating, flight review, or instrument proficiency check, and for currency. This means that a pilot does not need to record every single one of his or her flights.
A visual flight rules (VFR) aircraft on a long, straight-in approach for landing never enters the traffic pattern unless performing a go-around or touch and go after landing (see paragraph 9.5). referring to the AIM and the PHAK.
VFR flight plans filed with AFSS (Automated Flight Service Station) are not passed to ATC. They remain strictly within the AFSS network for search and rescue purposes only. When you request VFR flight following outside the local approach control area, the controller will normally enter a mini-flight plan in the system.