I am looking at going to Montreal this summer and decided to see what it would take to train my way there.

Basically, it takes time.

I looked at two different route options: DEN to MTR via TOR or via ALB.

For your consideration.

Train Trip to Montreal via Toronto
DEP	City	City	ARR	Train Time	Layover Time	Trip Day
2010	DEN	CHI	1550	19:40	5:50	DAY 1-2
2200	CHI	BUF-depew	930	11:30	5:30	DAY 2-3
1456	BUF-depew	TOR	1937	4:40	16:00	DAY 3
1135	TOR	MTR	1704	5:30		DAY 4

Return
DEP	City	City	ARR	Train Time	Layover Time	Trip Day
1805	MTR	TOR	2326	5:21	9:00	DAY 1
830	TOR	BUF-depew	1325	5:05	10:30	DAY 2
2355	BUF-Depew	CHI	945	9:50	4:15	DAY 2-3
1400	CHI	DEN	715	17:15		DAY 3-4

Train Trip to Montreal Via Albany
DEP	City	City	ARR	Train Time	Layover Time	Trip Day
2010	DEN	CHI	1550	19:40	5:50	DAY 1-2
2200	CHI	ALB	1540	17:40	19:25	DAY 2-3
1105	ALB	MTR	1910	8:05		DAY 4

Return
DEP	City	City	ARR	Train Time	Layover Time	Trip Day
930	MTR	ALB	1740	8:10	1:35	DAY 1
1905	ALB	CHI	945	14:40	4:15	DAY 1-2
1400	CHI	DEN	715	17:15		DAY 2-3

No matter which way you go, you will need to overnight in either Toronto or Albany.

So the Optimal way to train it seems to be go via Toronto. That is a nice city to visit plus there are a number of TOR-MTR trains to choose from if you don’t want to catch the 1135. I I actually ignored some earlier trains so I could sleep in.

And Return via Albany, where the are minimal layover times and you can get back to Denver in three days.