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In this post, I’ll include everything related to my seven pillars (see also How to Live Guide: Practical ). I’ve done this before in an older blog, but that work is unfortunately lost to me for now. So, I’ll simply begin again...starting from today, at random. 7 pillars Mental and Physical Health Artificial Intelligence Finances and Future Relationships, Friends & Family Improving the World: Nature & Humanity How to Live: Practical & Theoretical (Life Hacks, Philosophy, ...) (see here for practical, for theoretical bacgound check out this  link ) Xplore the World & Knowledge Database (series, movies, anime, books, fun facts, interests,...) 24-8-2025 (sunday, free) Mental and Physical Health Nothing particularly noteworthy today. I cleaned my house a bit, brought more order to my kitchen, and did the laundry. I also prepared my bag for work tomorrow. My eating habits weren’t ideal, I even picked up a pitta and some French fries from the local shop. Artificial Intelli...

Gameproject 1: "The Oregon Trail"

 Best Order to Play The Oregon Trail Games for the Complete Experience

The Oregon Trail games are a historical simulation series where players guide a group of settlers on their journey to Oregon in the 19th century. While the games don’t have a strict overarching lore like some RPGs, playing them in a certain order can provide a more immersive and complete historical experience.

Chronological Order for a Complete Oregon Trail Experience

Below is an action list that ensures you experience the games, books, and other media in the best order—without spoilers—while fully immersing yourself in the historical setting.

1. Historical Background & Immersion

(Before playing the games, understanding the historical context enhances the experience.)

📖 Books & Resources:

  • "Undaunted Courage" – Stephen Ambrose (about the Lewis & Clark expedition, which laid the foundation for the Oregon Trail)
  • "Westward Expansion: A History of the American Frontier" – Ray Allen Billington
  • "Women’s Diaries of the Westward Journey" – Lillian Schlissel (real diaries from women who made the journey)
  • Watch documentaries on the American West, such as Ken Burns' The West

2. Playing the Games in Chronological Order (No Spoilers, Maximum Immersion)

🏕 PREQUEL ERA (Before The Oregon Trail)

  1. The Yukon Trail (1994) – Set during the 1890s Klondike Gold Rush, this game isn’t directly related to The Oregon Trail but provides insight into the hardships of travel and survival.
  2. Lewis & Clark Interactive Journey (1998) – Follows the real-life expedition that paved the way for the Oregon Trail migration.

🚂 THE CORE OREGON TRAIL ERA

  1. The Oregon Trail (1971 / 1985 / 1990 / 1992 / 1993 / 2001 / 2021 versions)
  2. The Oregon Trail II (1995) – A more in-depth expansion of the game with added realism and choices.
  3. The Oregon Trail 3rd Edition (1997) – A modernized version with better graphics and improved accuracy.
  4. The Oregon Trail 4th Edition (1999) – Adds more educational elements and player interactions.
  5. The Oregon Trail 5th Edition (2002) – The most feature-rich classic version, including some story-driven elements.

🏡 POST-OREGON TRAIL ERA (Settlements & the Wild West)

  1. The American Girls: Kirsten’s Journey (1996) – A story-driven game about a Swedish immigrant girl traveling the Oregon Trail and settling in America.
  2. The Westward Series (2006-2010) – Simulation games where you build your own settlement in the Wild West.
  3. The Organ Trail (2010) – A parody featuring a zombie-apocalypse twist but with the same survival mechanics as The Oregon Trail.

3. Additional Media & Final Touches

📺 Films & TV Shows:

  • Meek’s Cutoff (2010) – A realistic portrayal of pioneers traveling the Oregon Trail.
  • Into the West (2005) – A miniseries about westward expansion from multiple perspectives.
  • Centennial (1978) – A historical drama about the American frontier.

🎲 Extra Games (Optional):

  • Red Dead Redemption 2 – A realistic depiction of late 19th-century frontier life.
  • Sid Meier’s Colonization – Covers an earlier period (1600-1800) but helps understand the transition to the Oregon Trail era.


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