One has the option of taking a computer generated 'package deal', ostensibly offered by the trailhead town's merchants and sized for five or six months of consumables. Outfitting the supplies and choosing the parties equipment of their journey becomes a possible point of player control leading to increased scoring chances. Players with the cooking skill are able to increase the nutrition value in their food. For example, players with the botany skill are more likely to find edible plants.

Each skill raises the chance of something happening or not happening. If the player does not select any skills, they will be converted into bonus points at the end of the game. Automatic skills, based on the occupation, are free. Finally, there is a skills screen where players may spend 120 points on extra skills: medical, farming/animals, botany, and sharpshooting, to name a few. Also, they may select how many others are with them in their wagon, along with their names and ages this drastically added to the game's popularity as players could seemingly 'live out' the journey with friends and family. The online guidebook resource alters its displayed help based upon the year of travel, but not with the target and trailhead ends chosen - hence to read the book, one needs wade past pages of useless information applicable to sub-scenarios (such as alternate routes over a local regional stretch) one hasn't chosen.ДЄt the beginning ('New Game'), players may start a new game where they choose their name, occupation, level, date of travel, their starting point and destination, and type of wagon. Travel is much easier in later years, as there are more towns and trading posts along the way to resupply your party. This version also allows the player to choose between 20 years of travel (rather than 1 in the original) from 1840 to 1860.

Players are also able to talk with other settlers along the way and ask their advice when needed. an accident or illness) happens, the game halts and the player must decide what to do in response, so it is much more interactive. For instance, rafting down the Columbia River is a much greater challenge than it was in the original game. Oregon Trail 5 includes far more detail than the original.

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