It is unclear when or how the roll developed. Nothing like it can be found in Mexico (the source of much cowboy equipment, notably the saddle, bridle, lariat, chaps, wide-brimmed hat, high-heeled boots, and spurs), or in the Southern United States, the birthplace of many cowboys. However, one item just predating the "Cowboy" era that was very familiar to most Cowboys, many of whom were American Civil War (ACW) veterans, was the Confederate soldier's rolled bedding that was carried slipped diagionally over one shoulder and tied together just over one hip. A vital part of this "bedding roll" was the "rubber blanket", a rectangle of heavy canvas with brass eyelets at the corners and edges, that was heavily coated with vulcanized "Goodyear" latex rubber. Each Federal soldier was issued one, but both sides write of having acquired two or more, either through capture or acquisition on the battlefield. This rubber blanket was carried rolled around the rolled-up wool blanket and served as a groundcloth (or sunshade, or hasty tent,) or any other purpose the soldier could devise. This rubber blanket was very waterproof and made it possible for the soldier to sleep realitively dry for the first time in the history of warfare. Prior to this time, most soldiers of the world's regular armies, may or may not have been issued a wool blanket. Very crude groundcloths of "painted canvas" were sometimes secured by the soldier themselves, but at best, the soldier could count on waking wet and cold. In the ACW, the usual practice was to spread one rubber blanket on the ground, arrange the wool blanket on the rubber blanket, and, if available, spread a second rubber blanket on top of the wool blanket. The soldier slept directly on the rubber blanket, uncoated side up, and the wool blanket over the recumbant soldier. In practice, it almost duplicated the Cowboy Bedroll. The addition of the waterproof tarp of the Cowboy Bedroll may well have descended from this source. The bedroll is not prefigured in the history of the Midwestern United States, where several of the older states, notably Ohio, Indiana, Illinois, Iowa, and Missouri, were noted c. 1830-65 as breeding and finishing grounds for great numbers of cattle, and from which these cattle were routinely "walked" to markets as far east as New York City, until the wholesale introduction, in the postbellum era, of farming machinery caused an economic shift toward grain culture, primarily wheat and corn. Photographs exist of it, notably one in Albert Marrin’s Cowboys, Indians, and Gunfighters, but they tend not to be specifically dated. Will James, writing 1924-42, referred to the bedroll and portrayed it in his sketches, as did Stan Lynde. Louis L’Amour, who took some pride in the authenticity of his backgrounds, suggested in The Cherokee Trail (set c. 1863) that the roll may have existed as early as the Civil War, as he has a character say he’ll "just throw my bed under that tree." It may have developed from the elementary bedding used by the mountain man, who generally used only a Mackinaw blanket and a buffalo robe or bearskin, cured with the hair on. The one certainty is that it was widespread, as authors on the subject generally agree that most roundups and trail drives had at least one "bed wagon" (sometimes more), specifically intended for the transport of cowboys’ personal beds and other belongings.
The foundation of the bedroll consisted of a thoroughly waterproofed white canvas tarpaulin made of Number Eight ducking weighing, most often, 18 oz. per square yard (i.e., 9 sq. ft.), and measuring either 6x14ft. or 7x18. (The reprinted 1897 Sears Roebuck Catalog lists "stockmen’s bed sheets" of "heavy white duck," with snap rings or eyelets, as 13-18 oz. for either size, but Fay Ward states that of the various weights of tarp (16-, 18-, 20-, and 22-ounce), the preferable one was "the 18-ounce type… a good water excluder, is not too heavy to manage and will stand a lot of rough handling.") The tarpaulin cover was made with a series of snaps and rings down either side so it could be folded over and snapped shut. Inside were two to four almost-square heavy quilts called "sougans," folded double, made of heavy wool or cotton batting quilted between patches of pants, coats, and overcoats, or sometimes of patches alone, weighing about 4 lb. each, and generally used as a pad. The sougans in turn enwrapped a blanket or two (woolen ones weighed 4-6 lb. per), a lightweight double blanket sheet 35" wide (about 1 lb. for 3.75 yd.), and sometimes, sandwiched between them as a mattress, a thin, feather-filled comfort (probable weight about 5 lb.) known in cowboy vernacular as a "henskin." (The modern cowboy uses a 4"-thick twin-size foam mattress, but this is the only significant change that has taken place in over a century.) The tarpaulin cost roughly $7.70-$11.60, depending on its weight; the sougans, about 28-30c. for two 3x7' rolls of cotton batting (the patches being more or less free); the blankets $1.10-$9.96 each; the sheeting 34-53c., and the henskin, if applicable, 96c.-$2.25, so the entire roll could be assembled for anywhere between $9.42 and $34.60. At the very core was the "war bag," generally an old gunny sack that had at one time held grain, feed, or even sugar, though some were of canvas, cotton, or oilskin. Earlier rolls (and those of riders traveling light, such as outlaws on the run) were wrapped in a canvas groundcloth, an oilskin cover, cowhide blanket, rubber blanket, or India-rubber "sleeping spread," and consisted of a blanket or two and perhaps a quilt, or even a couple of buffalo robes.
To prepare the bed for sleeping, the cowboy laid it out with the tarp folded roughly in half at the middle, creating a near-square 6–7 ft. wide and 7–9 ft. long, and centered his bedding between the two long edges, with the top side of the tarp (2.5 to 3 ft. longer than the bottom, so it could be pulled completely over his head if desired) turned back. If the weather looked threatening, he folded the sides under to the edge of the bedding, thereby preventing water from entering, and pulled the flap up when he turned in. In the morning, he spread the tarp out to its full extent, centered the bedding on the resulting oblong, and folded its two long edges up. He folded the tarp over on either side, fastening the hooks together, and placed his war bag near the upper end; folded the tarp over the bag, and tied it with a piece of thong so the bag would not slide around; and rolled the whole up into a cylinder. He secured it by means of a pair of leather straps with buckles, or with a couple of lengths of clothesline or worn-out lariat which he tied around it near the two ends, and a third piece of rope running from one of these to the other to form a handle. [See pictures in The Cowboy at Work, p. 46, and The Cowboy Life, p. 30.]
If the cowboy was working from headquarters or a line camp, he spread his roll on the floor or in a bunk. If he was out with "the wagon" (meaning a roundup or trail outfit), the bed was rolled and loaded to go along; the first thing he did after crawling out in the morning was to roll and tie it, pack it over to the bed wagon, and dump it where it would be conveniently at hand when camp-moving time came. (Not to do so was a serious breach of camp etiquette, and was moreover likely to earn the careless one the rough side of the cook’s tongue.) Often he sat on it while he ate, which was quite permissible as long as he moved it afterwards. If he went to town for a while he took his roll, which was also his trunk, and dumped it in the corner of his hotel or boarding-house room—or else unrolled it in a stable loft or in the trees down by the river, which was cheaper. If he was drifting over the range he tied it on his pack horse and it went wherever he did. In wet weather he took his hat, rope, boots, and spurs to bed with him; in cold weather his bridle came too. (Wet boots were hard to put on, and a wet rope was stiff and hard to handle; a cold bridle meant a cold bit, and the horse would fight it.) In rainy, snowy, windy, and/or sleety weather, he pulled up the canvas flaps of his roll and remained snug and warm (the waterproof tarpaulin underneath him kept ground moisture from seeping in). If the roll was covered with snow and ice during the night, the extra weight made it that much warmer inside. If when he woke it was freezing cold outside, he dressed a la Pullman berth, without quitting his warm blankets. If, on the other hand, the weather was warm, he could arrange his blankets in such a way as to have most of them underneath him and only one (perhaps the blanket sheet) over him. Some men also carried a 3-ft. canvas triangle with a grommet at each corner and another centering each edge; this could be rigged in half-a dozen ways as a windbreak or rain-roof, or rolled and shoved under the sougans for a pillow. Near the foot the cowboy kept his hobbles, latigo straps, dirty laundry, extra (usually fancy) spurs, and whatever else he might happen to have. If he owned a suit (4-5 lb.) and a couple of good shirts (1.25-1.875 lb.) for dressy wear, they were tucked in between the sougans, where they stayed both clean and wrinkle-free.
The war bag seems to have been used primarily as a pillow and for clothing (which provided the stuffing), and it is likely that the cowboy rolled each item up in a tight cylinder, as the modern backpacker does, to save space. He generally had, besides what he was wearing, a change or two of trousers or jeans, one or two sets of underwear, and one to four shirts, as well as clean socks and perhaps a second pair of boots. A lightweight jacket, such as a denim jumper, and an extra vest would be kept there too. This would come to a total of about 23-26 lb., or as much as 33 if "good" clothing was present, plus the bedding itself, which ran roughly 30-44, not counting anything else he might have tucked away in the bag (ranging from extra tobacco to books to personal papers to odd small collectibles, jewelry, etc., which was why it was considered unhealthy to be caught prowling through another man’s bedroll). The roll also made a cylinder 12 to 14 inches thick, which was both too bulky and too heavy to tie behind the cantle of a saddle. Thus the cowboy would need a pack horse as well as his mount.
While some writers [Marrin, Wayne Swanson in Why the West Was Wild] claim that cowboys seldom if ever had horses of their own, this is not only untrue but basically impossible. Ranchers routinely laid off 50 to 70% of their crews for the winter; these men had to search for new jobs or simply "ride the grub line" until spring. Ranches sometimes failed, and their hands were cast adrift. Or a cowboy might disagree with his boss or foreman, or simply get "a hankering" to see new country. Since he seldom had enough money to travel by train or stagecoach, his only option was horseback. (The misconception of the authors cited may come from the fact that each cowboy did have a "string" of ranch-owned horses "cut" to him upon hire, because all range ponies were grass-fed and had to be changed at least once a day when at heavy work, and because the cowboy himself seldom owned a well-trained specialized horse, such as a roping or cutting one.) And while he could legitimately claim food and lodging free of charge at any private home he came to (even if nobody was home at the time), distances in the West were such that he might sometimes be caught midway between around camping time, so he would also have to have a "camp outfit" (cooking utensils, plate, cup, cutlery), food supplies, and perhaps some fishing gear and trap lines. By the 1890s, if not before, he could purchase for this purpose a compact camping kit of all necessary basic items, including a "skeleton stove" (a steel grill on legs to place over the campfire); these were made by various companies and often advertised as "patent." They ranged from 15 to 53 pieces, weighed a maximum 80 lb., cost at most about $18, and could be packed up in a single unit of about one cubic foot [see pictures, Sears, p. 610, and Montgomery Ward, p. 503]; such an object could easily be slipped into a pannier and slung on one side of a pack saddle, balanced on the other side of the horse with a second one containing the cowboy's food (and perhaps a nosebag of oats or maize for each horse), while the rolled bedroll, being to some extent flexible, could be crammed between the forks of the saddle on top, and the whole neatly covered with a tarpaulin secured with a diamond hitch. Historians of the cowboy therefore speak of his "personal horses." He probably changed off each day, because his pack, being dead weight, would sit more heavily on the horse bearing it than would a human being of equivalent poundage.
In his saddlebags the cowboy would carry small items which might be difficult to recover in a packed war bag, or things he might need in a hurry, such as extra ammunition or a rough-shoeing kit for use in case one of his horses lost a shoe. A currybrush and comb, his own razor and strop, toothbrush, cake of soap, gun-cleaning kit, elementary medical supplies, hobbles, calf ties, a bottle or waterproof pouch of tinder, a box of matches, a small camp ax, string and thong, an awl, fishhooks and line, snare lines and trigger pins, a "housewife" (portable sewing kit such as was carried by most soldiers during the Civil War), flint and steel (in case his matches got wet), a deck or two of cards, bandannas, an extra bit, cinch, or spurs, a mouth organ, small telescope, and any horsehair work or tooled leather with which he was currently occupied were other possibilities. Atop these would be fastened a slicker or poncho, to be easily accessible in case the weather turned, and quite possibly a winter jacket. On the pommel would hang a canteen and the stake rope and picket peg for the saddle horse, while those of the pack animal would probably ride in a saddlebag.