Do they still carry passengers between Skagway and Bennett only? If so, it does appear that you wouldn't get a meal.
I've thought about riding to Bennet and back, and hiking down the Chilkoot Trail to Bare Loon Lake or Dan Johnson Lake and back. It looks like you could do it. It's four miles from Bennett to Bare Loon Lake, and four-and-a-half to Dan Johnson Lake. The are four hours and 55 minutes between the arrival of the northbound train and departure of the southbound train.
At Bare Loon, if no one else is around, you could take off your clothes, and get in and out of the water, real fast - it is cold. That's how the lake got its present name in the 1970's. In the 1970's, recreational hikers started using Chilkoot Trail. These hikers would skinny dip at this lake before getting to the train, so they wouldn't smell. They also heard loons wail at this lake. Hence, "Bare Loon." Before the 1970's, it used to be called "Beaver Lake," but there are 14 other "Beaver Lake"s in British Columbia. So, when hikers started calling it "Bare Loon," the new name stuck.
Robert