Halloween Ride with the Doggo to Wallingford

Oct 31, 2026

On Halloween day, Ann, Kai, and I geared up for another cruise down to Wallingford. We wanted to make sure our furry co-pilot stayed secure and comfortable, so we tried a new setup: securing him facing forward with a dual-leash arrangement and lining the trailer floor with his favorite doggie bed.

Bruce accompanied us down to the intersection with Creek Road and Walker Mountain Road where he turned around and headed back to the house.

The ride out, however, was filled with a lot of whimpering. At first, I figured he had to pee—a lesson we learned the hard way on our last trip. But when we pulled over for a walk, he didn't do a thing.

Thinking about it now, the issue wasn't a bathroom emergency or physical discomfort. He was likely just complaining because the rigid setup prevented him from turning around to look at Ann. Future rides will definitely require a bit more freedom of movement so he can keep his eyes on both of us.

Once we rolled into Wallingford, we decided to skip the usual food stop and spend our time cruising the neighborhood streets instead. The town went all out for the holiday. The Halloween displays were fantastic, with several houses going completely over-the-top with their spooky decorations.

The real victory of the afternoon came on the return trip. Despite passing a few rowdy, barking yard dogs along our route, Kai behaved beautifully, kept his cool, and rode like a total pro all the way home.