On or about April 17, 1865, the steamer Twilight, assembled at local iron and mill works, though its makers' names are unknown, began life on the St. Louis waterfront as a mountain boat. The immediate goal of its master and six owners: steam upriver with cargo and passengers to the flourishing gold fields and mining settlements near Fort Benton. Valued at $35,000 and insured for $30,000, the boat was "heavily loaded" with guns and ammunition, provisions, machinery, perishable food, gin and whiskey; it carried nearly 200 passengers. Its savvy owners and pilot knew that the Twilight could profit as much as $50,000 on a successful round trip and thus were eager to start.
William Massie was the Twilight's master. His name was legendary among upper river pilots. The safety of the vessel, passengers and cargo depended on the decisions of the pilot, explains Hanson. "His word was a law before which every one bowed. The captain loomed exceedingly small beside the truly despotic lord of the old-time river, the pilot."
Because of the continually combative Indians, the Twilight was accompanied on its trip by another steamer, the Cora, which unfortunately hit a snag and sank near Omaha. All the Cora passengers boarded the Twilight for the continued journey to Fort Benton. Another steamer, the Lillie Martin, replaced the Cora for the remainder of the upriver run.
After nearly 11 weeks, Massie and his crew reached Fort Benton in June 1865. It wasn't a perfect trip for the passengers, as they were forced by low water to disembark below Fort Benton and walk to the post while the Twilight awaited a rise in the stream to haul its cargo to port. The Twilight was reportedly the last steamer to arrive at Fort Benton in 1865, where low waters and uncertain weather caused riverboat owners to question the wisdom of heading north in the early fall. Nevertheless, once the Twilight returned to St. Louis from its first Fort Benton circuit, it loaded up with cargo and passengers fully intending to reach Fort Benton again in 1865—around mid-to-late October.
A few passengers from the first round trip, most paying $100 one-way fares, wrote about their Twilight journeys. One recalled meeting a fleet of mackinaws—open boats—coming downriver. Women, engaged to marry goldfield region soldiers and miners aboard the mackinaws, were anxious passengers on the Twilight. The vessels stopped. The fiances and a minister left the mackinaws and boarded the Twilight. Within the hour, the minister had performed 16 marriages. Will J. wrote to a newspaper in August, 1865 that "for hundreds of miles, the scenery is dull, uninteresting and monotonous" until arriving at the early reaches of the Rockies. South of Fort Benton, the rocky, shallow Dauphin Rapids provided the greatest physical challenge to upriver steamers, he declared. But it was the weather, he continued, that offered "the most objectionable feature" of the journey. "You may lie down for a nap, sweltering with heat and perspiration, and awake an hour afterward with a vivid impression upon your mind that you are on an expedition...and have become frozen in among the icebergs."
Hiram D. Upham, later the main Indian agent at Fort Benton, wrote letters to relatives while aboard the Twilight; they were published in 1933 by the State University of Montana. Upham confirmed that the Twilight, while armed with a protective 12-pound cannon, traveled only during daylight hours because of dangers at night from snags, chutes, and testy bends and from furtive Indian attacks. "We have been struck four times (by snags) but luckily for us none of them went through the hull." Whenever a powerful wind storm arose, he said, the Twilight headed to shore to wait it out. Upham and other passengers saw grizzly bears, wolves, antelope, deer, and elk as they ascended the Missouri, and buffaloes, too.
"I believe I have seen 50,000 buffaloes within the last two weeks," Upham wrote. "They are continually swimming across the river in droves and very often they get caught up in the current and carried right down by the boat so close that they are often struck by the wheels. The deck hands can take a lasso and catch them in the water any day."
Upham told of passing key American Fur Co. outposts—Fort Rice and Fort Sully among them—as well as the government post, Fort Union, which, he said was garrisoned by "paroled (Civil War) Rebel soldiers." He stated that of 20 steamers that left St. Louis for Fort Benton in 1865, only four, including the Twilight, actually arrived. Three sank and the rest were forced by low water or other problems to turn around and head toward St. Louis. Another Twilight passenger, Charles Rumley, commented that "all the passengers reached Benton safely except one young man who died from eating toadstools which he mistook for mushrooms." The trip from St. Louis took 72 days (according to Upham) and 76 days (according to Rumley).