| Achievement | How to unlock
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| - Explored the Customize Truck Menu.
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| - Got all Golds in Midland, Texas.
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| - Get a Perfect Day (Standard Mode) in Jackson, Mississippi on Route D, Day 2 using a 31-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Boise, Idaho on Route C, Day 2 using a 21-point menu or above.
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| - Got all Bronze in any territory.
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| - Get a Perfect Day (Standard Mode) in Wichita, Kansas on Route D, Day 2 using a 21-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Nashville, Tennessee on Route J, Day 1 using a 40-point menu or above.
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- Does Anyone Actually Like Houston?
| - Get a Perfect Day (Standard Mode) in Houston, Texas on Route C, Day 4 using a 24-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Mobile, Alabama on Route E, Day 5 using a 34-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Wichita, Kansas on Route B, Day 4 using a 19-point menu or above.
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| - Got all Golds in New Orleans, Louisiana.
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| - Got all Golds in Wall, South Dakota.
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| - Got all Golds in Jackson, Mississippi.
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| - Got all Golds in Wichita, Kansas.
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| - Got all Golds in Moab, Utah.
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| - Got all Golds in Nashville, Tennessee.
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| - Got all Golds in Mobile, Alabama.
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| - Got all Golds in the Iron Cook Speedway.
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| - Got all Golds in Boise, Idaho.
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| - Got all Golds in Marietta, Oklahoma.
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| - Got all Golds in Houston, Texas.
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| - Get a Perfect Day (Standard Mode) in Iron Cook Speedway on Route F, Day 3 using a 36-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Midland, Texas on Route C, Day 2 using a 26-point menu or above.
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| - Got a medal on the first day in Houston, Texas.
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| - Got a medal on the first day of Jackson, Mississippi.
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| - Get a Perfect Day (Standard Mode) in Boise, Idaho on Route A, Day 3 using a 6-point menu.
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| - Get a Perfect Day (Standard Mode) in Mobile, Alabama on Route H, Day 1 using a 34-point menu or above.
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| - Got a medal on the first day in Marietta, Oklahoma.
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| - After loading a saved game, input the "classic code" in the main menu and get a gold in any day.
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| - Got a medal on the first day in Wall, South Dakota.
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| - Get a Perfect Day (Standard Mode) in Jackson, Mississippi on Route H, Day 5 using a 31-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Moab, Utah on Route E, Day 3 using a 23-point menu or above.
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- Obese Jake's INSANE Challenge
| - Get a Perfect Day (Standard Mode) in Marietta, Oklahoma on Route I, Day 5 using a 23-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Wall, South Dakota on Route D, Day 5 using a 15-point menu.
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| - Got a medal on the first day of Mobile, Alabama.
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- Pour One Out for Crazy Dave
| - Get a Perfect Day (Standard Mode) in Marietta, Oklahoma on Route D, Day 5 using a 19-point menu or above.
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| - Got a medal on the first day in Moab, Utah.
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| - Get a Perfect Day (Standard Mode) in New Orleans, Louisiana on Route I, Day 3 using a 22-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Wall, South Dakota on Route A, Day 3 using an 18-point menu or above.
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| - Got all Silver in any territory.
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| - Get a Perfect Day (Standard Mode) in Boise, Idaho on Route B, Day 3 using an 18-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Houston, Texas on Route F, Day 3 using a 26-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Nashville, Tennessee on Route C, Day 2 using a 29-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Moab, Utah on Route G, Day 5 using a 21-point menu or above.
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| - Get a Perfect Day (Standard Mode) in Iron Cook Speedway on Route J, Day 3 using a 44-point menu or above.
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| - Got a medal on the first day in Midland, Texas.
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| - Got a medal on the first race of Iron Cook Speedway.
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| - Get a Perfect Day (Standard Mode) in Midland, Texas on Route A, Day 3 using a 28-point menu or above.
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| - Got a medal on the first day in New Orleans, Louisiana.
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| - Get a Perfect Day (Standard Mode) in New Orleans, Louisiana on Route J, Day 1 using a 22-point menu or above.
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- We Are in Kansas, Actually
| - Got a medal on the first day in Wichita, Kansas.
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| - Got a medal on the first day of Nashville, Tennessee.
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