I'm not sure how Oswald contributes to the plot of A Rift in Time, but he's been pure, monochromatic fun ever since he arrived in Disney Dreamlight Valley.

Oswald’s Friendship Missions in DDV have seen us firefight in his amphitheater home, tell bedtime stories to living and breathing alarm clocks, and now craft and ground a Vintage Trolley. While these missions are fun, some of the steps you’ll need to take to complete them are a bit complex, especially when it comes to gathering resources. In this guide, I’ll show you how to complete Erratic Transport in Disney Dreamlight Valley.

To find the Vintage Trolley Conductor Hat in Ancient's Landing, use the Royal Hourglass around Ancient's Landing, specifically near The Docks. You're looking for a black and white hat.

Once you have it, show it to Oswald, he asks you to put it on and make a Trolley.