My longest end to end trip with breaks was thirty days, back when the North America Rail Pass still existed. My travelogue is still available (in annoying reverse order) as a blog
here. Aside from a four nights in a section between Winnipeg and Churchill, MB, everything was in coach with one, two or three night stops en route so as stretch out a bit, do some sightseeing and visit friends along the way.
The precise itinerary went as follows:
MAY:
Fri 21 ‘Adirondack’ dep. Montréal 09:50 arr. Schenectady 16:23
Fri 21 ‘Lake Shore Ltd’ dep. Schenectady 19:16
Sat 22 arr. Chicago 09:30
Sun 23 ‘California Zephyr’ dep. Chicago 13:50
Mon 24 arr. Denver 07:15
Tue 25 ‘California Zephyr’ dep. Denver 08:05
Wed 26 arr. Emeryville 16:49
Thu 27 in San Francisco
Fri 28 drive to Santa Barbara
Sat 29 drive north, ‘Coast Starlight’ dep. Emeryville 22:02
Sun 30 arr. Seattle 20:30
APRIL:
Mon 1 in Seattle
Tue 2 ‘Amtrak Cascades’ dep. Seattle 07:45 arr. Vancouver 11:40
Tue 2 ‘Canadian’ dep. Vancouver 17:30
Wed 3 arr. Edmonton 17:30
Thu 4 in Edmonton
Fri 5 in Edmonton
Sat 6 ‘Canadian’ dep. Edmonton 18:20
Sun 7 arr. Winnipeg 11:20 / ‘Hudson Bay’ dep. Winnipeg 20:45
Mon 8 on board the ‘Hudson Bay’
Tue 9 arr. Churchill 08:30 / ‘Hudson Bay’ dep. Churchill 20:30
Wed 10 on board the ‘Hudson Bay’
Thu 11 arr. Winnipeg 08:05 / ‘The Canadian’ dep. Winnipeg 12:25
Fri 12 arr. Toronto 20:00
Sat 13 VIA Corridor dep. Toronto 15:10 arr. Montréal 19:48
Sun 14 ‘Ocean’ dep. Montréal 18:30
Mon 15 arr. Halifax 16:20
Tue 16 in Halifax
Wed 17 in Halifax
Thu 18 in Halifax
Fri 19 ‘Ocean’ dep. Halifax 12:35
Sat 20 arr. Montréal 08:15