I've yet to be bowled over by a Kelly Reichardt film. I didn't like Old Joy, and had a more positive reaction to Wendy and Lucy and First Cow. Meek's Cutoff is somewhere between all of those. It looks like a realistic portrait of what it was like on the Oregon Trail in 1845: dirt, dust, no water, boring. Ironically, I had no idea it was based in part on real life events (there was a real Stephen Meek who had found the Cutoff that bears his name). Honestly, it was irrelevant that the story was "real" ... what mattered was how effectively Reichardt gave us a wagon train of settlers fighting the elements and the uncertain skills of Meek, their guide.
Meek's Cutoff is the kind of film that does such a good job of presenting the crushing boredom of the situation that the movie itself becomes boring. I don't know that there is a fix-it for this. Give us some standard action and the verisimilitude at the heart of the picture would be ruined. Reichardt relies on the changing interactions between the settlers and Meek for provide some forward movement. There is also an Indian (that's his name in the credits, "The Indian") captured by Meek ... while he speaks no English, somehow it is communicated to him that they are looking for water, while the racist Meek just wants to kill him. There's a will he/won't he angle that provides a bit of suspense, but in the end, Reichardt resists making too much of that suspense. She focuses on the interplay between the characters and the growing mistrust of the settlers for Meek.
The film's ending emphasizes this. The group must decide who to follow, Meek or the Indian. As the Indian walks in the direction of what we assume he believes to be water, the settlers ponder what to do. And the screen goes to black, and the credits roll. I thought this was a cheat, but perhaps it's appropriate the ultimate result is left up in the air. For me, it was a final frustration with a film I never warmed to, although it didn't inspire the hatred I had for Old Joy. #927 on the They Shoot Pictures, Don't They list of the top 1000 films of all time (#117 on the 21st-century list).