For me, it was Louisiana to Pennsylvania and back, 1389 miles each way. My family made this trip at least six times. Then we wised up and flew instead. The last time, my mother and aunt drove up to Pennsylvania to pick me up. Then we went back to Louisiana. They also nearly let me suffocate on a plastic bag holding one of the myriad quilts we bought in Tennessee. (I fell asleep on it.)
Well I would have to say it was from Indianapolis to Albuquerque via Little Rock. Jeez that took a long time but it was a good trip.
The worst road trip was from Mosul, Iraq to Camp Wolf, Kuwait. That took two days in the incredible heat. Our HMMWV broke down three times, and we decided to drop the trailer somewhere south of Baghdad.
We did a lot of road trips when I was a kid.
When I was a kid we took trips during the summer to various ANS(American Nuclear Society) and NRC meetings. My dad did nuclear reactor saftey research (now retired) so the trips were for the most part paid by for by the government if my Dad drove. Dad still had to pay for the room for the kids but overall the vacations were cheaper. The government paid for the gas. The down side was that Dad worked during the week while we went and did the tourist bit. This was mostly in the late 70’s and early 80’s.
We drove from Albuquerque NM to the Florida Keys on one trip. I think the meeting was in Miami and we headed further down south after the meeting. We drove back non-stop from the Keys to Albuquerque. That drive sucked. According to google maps it is over 2100 miles. My Dad could drive for like 15 to 18 hours at a time. It was a long trip.
We also drove from ABQ to New York. That is 2,177 milies according to google. We got pretty good at the drives though my Dad never wanted to make bathroom breaks. It was always ‘you can hold it, it’s only x miles until we stop’. The bummer was that x always = some ungodly number.
I also seem to remember a trip from ABQ to D.C. then up to Wisconsin and finally back to ABQ.
On the bright side I’ve been to 43 or 47 states. I forget exactly and don’t feel like counting right now but I’ll probably make every state in the country before too long.
I also did a drive from ABQ to D.C. when I got promoted and had to relocate. I did that one alone with three pissed off cats in a U-Haul while towing a car. In three and a half days. That trip sucked. Especially when I found out that the HR department screwed up and I had an extra week to make the trip.
Slee
3667 miles. Kansas to Atlanta to Jacksonville to New Orleans back to Kansas.
Took us 2 tires a water pump and a quick fix on a hose about to burst to get back. Not to mention it took all the extra money and days to make it back in time. Actually I drove back into Kansas with something like 27 cents. And barely made my plane back home.
Good times.
I hitchhiked from Hamilton, Ontario, to Niagara Falls, to Windsor, then north and west to Vancouver, with a detour to Saskatoon, and all the way back to Hamilton, July-October of 1976. Boy, the stories I could tell about that trip!
I drove a semi back in the 1980s, 48 states. Three years, 3000-6000 miles a week, criss crossing the USA hither and yon. It was really fun, and really hard work.
To this day I love road trips, and if I have the time (and money for gas, these days) I would much rather drive than fly.
I’ve also driven from the Isle of Skye (Scotland) to Alonysus (Greece.) Some of that involved ferries though, and I can’t remember how many miles it was. It involved going through lots of funny little countries though. 
In the summer of 1984, my parents, sister, uncle and I took a trip to Mexico. We took this route:
Los Angeles --> San Diego --> El Paso --> Mexico City --> Acapulco --> Mazatlan --> Tepic, Nayarit --> Tijuana --> San Diego --> Los Angeles.
It appears I am amatuer for the Indy - Little Rock - ABQ only a meager 1460 miles. I can find no where to calculate Mosul to Kuwait City . .arg
The longest I ever took was a solo trip, Connecticut to PA to Georgia and back, over the course of 5 days. The longest non-stop (as in, not stop for anything other than gas) was Connecticut to Ontario (and back), which was also a solo trip. ALthough now that I think about it, it seems that North Carolina might be farther away than Ottawa was, and I can’t even count how many times I’ve done that trip, both alone and accompanied.
As a kid it would be LA to Miami and back to visit my dad’s relative’s in Louisiana and his parents in Miami. Urgh but I saw a lot of the country.
From Austin in 1993. A friend was getting married in San Francisco. At the last moment I found a rider who wanted to go to a Grateful Dead concert in Las Vegas. We drove nonstop to Las Vegas. I slept for six hours on a hotel room floor, replaced the clogged radiator in my beater car, then drove through the night to arrive in SF in time for the wedding. 36 hours later, I/we went back the way we came.
I once went on a school trip from Wellington in south west England to Italy and for some reason we went by coach. I don’t know the distance involved but it took something like 27 hours non-stop (unless you count the ferry crossing).
Last year I hitch-hiked from South Wales to Morocco. Again, there’s ferries involved obviously, but that’s somewhere in the region of 1600 miles.
I went on a crappy tour when I was 11. We drove from California to the Grand Canyon to the Hoover Dam to Las Vegas to Tijuana, returning to California after each destination. I dunno how far we travelled but I do remember spending most of my “vacation” on a bus.
Maine to Oregon when I started graduate school. Almost 4000 miles.
Oregon - Seattle - Ithaca, NY on the way back.
I got nothing on my brother, though. He BIKED from Oregon to Maine. In about 40 days.
Fort Worth (TX) - ABQ - Gallup - Barstow - Redding - Salem - Seattle. Made the trip twice in 1988.
Fort Worth - Baton Rouge - Destin - Orlando - Key West - Tampa - Chatahootchee (FL) - Meridian (MS) - Fort Worth. Family Vacation (RV)
Fort Worth - Amarillo - Raton - Laramie (WY) - Yellowstone - Utah - Monument Valley - Gallup - Amarillo - Fort Worth.
Family Vacation (RV)
I don’t know which one of these is longest. Probably the Seattle trip.
Milwaukee to Gwinett, Ga non-stop in which I hit Atlanta at rush hour.
Daytona Beach to Baltimore non-stop in which I hit DC at rush hour.
Miami to Minneapolis which I planned before hand and sailed straight through.
I love road trips, haven’t had a really long one in too long…my current job doesn’t give me enough vacation time for it. But when I had two weeks to spare, my family and I drove (with many stops along the way, this is just to illustrate the general route):
January 1996 - New York City - Cincinnati - Memphis - along I-40 to Grand Canyon - Las Vegas - Los Angeles - San Diego - along I-10 to New Orleans - Atlanta - New York City
June 1997 - New York City - Cincinnati - Memphis - Branson, MO - St. Louis - along I-70 into Utah - Salt Lake City - Craters of the Moon, ID - Yellowstone - Mount Rushmore - along I-90 to Vermillion, SD - Omaha - Chicago - Indianapolis - Fort Wayne - New York City
August 1998 - New York City - Detroit - Barabo, WI - Wisconsin Dells - Appleton, WI - Minneapolis - along I-94 till Little Bighorn National Monument, MT - Edmonton - Banff & Jasper - Calgary - Prince Albert, SK - Regina, SK - Winnipeg - along the north shore of Lake Superior until Toronto - New York City
Some of our “smaller” road trips have been pretty long, too.
I drove from north of Boston, MA to Marco Island FL via Atlanta, GA in the mid-nineties.
Gas and smokes were under $2 per “unit” down there, back then. Like the halcion days, or something.
Correction - in the January 1996 one I should have put Phoenix between San Diego and the I-10 stretch…forgot that it’s I-8 rather than I-10 that goes out of San Diego.
According to Google Earth’s measuring tool, 555 miles as the bird flies. I suppose if you have an hour to spend you can zoom in and follow every twist and turn of the roads.