Travel is much easier in later years, as there are more towns and trading posts along the way for resupply.

This version also allows the player to choose any year from 1840 through 1860 rather than being fixed to 1848 as it was in the original. At any point in the game, if the player dies, the game is over. Players are also able to talk with other settlers along the way and ask their advice. an accident or illness) happens, the game halts and the player must make a choice of action, so it is much more interactive than the previous version. For instance, rafting down the Columbia River is a much greater challenge than it was in the original game. Oregon Trail II includes far more detail than the original.

However, if the player settles at a destination other than the one they had selected at the start of the game, they will not receive a bonus, regardless of their chosen occupation. While some occupations have more money than others, the low income occupations get a greater final bonus, which proves crucial in getting a high score in the end of the game. Each skill can make good events more likely to happen, and bad events less likely to happen. The more important the skill is, the more it costs. The player chooses skills with a 120-point limit. After selecting an occupation, the player can select various skills. Also, they may select how many others are with them in their wagon, along with their names and ages. When players start a new game, they can choose their name, occupation, level, date of travel, their starting point and destination, and type of wagon. The CD-ROM came with an official strategy guide and certificate of authenticity, all packaged in a commemorative wooden storage box. In addition to the regular edition, MECC released a 25th Anniversary Limited Edition Oregon Trail II Computer Game. In contrast to the original version of the game, Oregon Trail II made an effort to include greater roles for women and racial minorities. It was redesigned with the help of American Studies PhD Wayne Studer. It is a revised version of the original The Oregon Trail video game.

Oregon Trail II is an educational video game released by MECC in 1995.

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