Longest trip (Distance and time): Madison, WI to Oregon, down the west coast, and back in a 182. Including mountain flying course, giving family/friends rides, sightseeing, etc. it came to 5800nm and 63.9 hours in the logbook.
Longest day (Distance, 1490+nm): Bremerton, WA to West Bend, WI. 11.0 hours in the Mooney. This also included my second-longest leg, from Sheridan, WY to West Bend.
Longest day (Time, 11.6): Round trip: Milwaukee to Madison (to pick up two other club officers) to Baltimore, MD and return all in one day to take a look at the R182 that is now in our club. A fuel stop in Indiana each way too.
Longest leg (Distance, 868nm): Santa Fe, NM to Boscobel, WI 844nm direct, 868nm as flown (via V263 SAF->TBE). One of my favorite legs ever - In the Mooney, at 13,000 feet I was truing 172 KTAS on 10.1 gph. With a nice westerly wind, it took 4:37 in the air and 53 gallons of fuel total!
Longest leg (Time): I think I hit 6.0 once in the Mooney but now I can't remember when it was! Might have been the Sheridan-West Bend leg from above.