The longest trip on Amtrak

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2013 Bloomington, Illinois to LAX (the long way-on the SSL) to SEA to GBB.

2015, Bloomington, Illinois to Chicago to Sacramento to Seattle to Vancouver to Toronto to Buffalo back to Chicago to Bloomington. All in sleepers. The CHI - BNL and back segment was on Ambus. They were working on high speed rail through Bloomington at the time.
 
I had one of these in 1978, and rode almost continually for 32 days, covering almost the entire long-distance system. You got the extra two days by boarding a transcontinental train on your last valid day. I was a lot younger then...😉
What was great about it then, was you didn't have to pre-plan your entire itinerary, but could be more serendipitous, and change plans at whim. Having more 'unreserved' trains helped that. Of course, you ran the risk of not being able to get on a train, and being 'stuck' somewhere...but I traveled at the most off-peak time of year...

U.S.A. Rail Pass graphic, 1970s. — Amtrak: History of America’s Railroad

The next year, I went to work for Amtrak...:cool:
 
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I've been from Pennsylvania to California three times: 1997, 2001/02, and 2015.

In 1997 and 2001/02, I took the Three Rivers and Southwest Chief both ways, stopping in Chicago both times at least once if not twice. In 2002, I also remember taking the San Joaquin and then the buses between LA and Bakersfield and from Stockton to Fremont? On the way back I took a Greyhound bus. I believe I have some ticket stubs in the "Restart the Broadway Limited" Facebook page in my signature from the 2001/02 trip.

In 2015, I took the Lake Shore Limited and California Zephyr, first stopping in Salt Lake City before the Bay Area. I then took a bus from San Jose to the Santa Barbara to the Pacific Surfliner to Irvine and then on the way back the Southwest Chief to the Capitol Limited, stopping in Chicago.
 
Actually I'm afraid I lied, longest trip was FUL-LAX-PDX-CHI On the Surfliner, Starlight, and Builder. Scheduled for nearly 76 hours but we were about 3-4 hours late into Chicago, so my trip time was closer to 79 hours.
 
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