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.
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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.
But as an instrument pilot, you have an option. 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.
You haven't flown through IMC without a clearance, have you? Technically, you can fly in IMC without a clearance in Class G airspace, because it's not controlled. Controlled airspace simply means you need a clearance to fly in the clouds. Class G airspace is uncontrolled, so it's not illegal to fly in the clouds.
If you purchased a round-trip flight and need to change the first leg to a different day, your best bet will likely be to pay the change fee and book a new flight. If you only need to change the return portion of a round trip, however, it may be cheaper to book a new one-way flight than to pay the cancellation fee.
No, pilots are not required to file a flight plan for every flight, but it is recommended for all flights, especially those that will be conducted outside of controlled airspace. Pilots flying under instrument flight rules (IFR) are required to file a flight plan.
Another option if the field isn't IFR and you can maintain your own terrain/obstruction clearance is to depart VFR and pick up an IFR clearance in the air with the proper approach/center (AIM 4-4-9).
There's a few things that can caused the ATC to cancel IFR: Your transponder is malfunctions, if you spawn into the flight mid-air, or on the runway, sometimes you never go through the entire IFR clearance process which makes your transponder to use the default squawk code.
14 CFR 91.169 (b) (2) (i) states that an alternate airport is not required if “for at least 1 hour before and for 1 hour after the estimated time of arrival the ceiling will be at least 2000 feet above the airport elevation and the visibility will be at least 3 statute miles.” To help remember those conditions of the ...
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.