Dynamic Watchlist Hub: Jan 23, 2026

10 Best Movies Like The Oregon Trail

If you loved The Oregon Trail, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for The Oregon Trail.

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#1
The Court Jester

The Court Jester

1955★ 7.3

Why watch this? A perfect follow-up to The Oregon Trail for fans of Music. It captures a similar light-hearted atmosphere.

A hapless carnival performer masquerades as the court jester as part of a plot against a usurper who has overthrown the rightful king of England....

#2
Alice in Wonderland

Alice in Wonderland

1951★ 7.2

Why watch this? A perfect follow-up to The Oregon Trail for fans of Animation. It captures a similar compelling atmosphere.

On a golden afternoon, wildly curious young Alice tumbles into the burrow and enters the merry, madcap world of Wonderland full of whimsical escapades....

#3
Mickey's Magical Christmas: Snowed in at the House of Mouse

Mickey's Magical Christmas: Snowed in at the House of Mouse

2001★ 6.9

Why watch this? A perfect follow-up to The Oregon Trail for fans of Animation. It captures a similar light-hearted atmosphere.

When a huge snowstorm leaves everyone stranded, Mickey and all of his guests at the House of Mouse, including Pooh, Belle, Snow White, Cinderella, Ariel and many more of his old an...

#4
Moscow, I Love You!

Moscow, I Love You!

2010★ 4.8

Why watch this? A perfect follow-up to The Oregon Trail for fans of Romance. It captures a similar light-hearted atmosphere.

18 directors, 18 novels, 18 short stories about Moscow......

#5
The Doctor

The Doctor

1991★ 6.4

Why watch this? A perfect follow-up to The Oregon Trail for fans of Drama. It captures a similar emotionally gripping atmosphere.

Jack McKee is a doctor with it all: he's successful, he's rich, and he has no problems.... until he is diagnosed with throat cancer. Now that he has seen medicine, hospitals, and d...

#6
Farewell Moscow

Farewell Moscow

1987★ 6.9

Why watch this? A perfect follow-up to The Oregon Trail for fans of Drama. It captures a similar emotionally gripping atmosphere.

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