Teddy Roosterbelt and the Ruff Riders
- Oscar the Pooch
- Sep 29
- 8 min read
I watched Devil’s Tower shrinking back into imagination through the back window as the Witch guided Wagon to South Dogkota.

“What do you suppose South Dogkota’s like?” I asked as the Witch welcomed us across the border.
“I have no idea,” Mom said. “All I know is that hardly anyone lives here and that there are badlands.”
I didn’t like the sound of that at all. “Well no wonder. I don’t want to live on bad lands either. What’s so bad about them?”
“Beats me.”
Something caught the magnet in Mom’s eyes and pulled her toward the front window. On the other side, the ground rose so suddenly that it looked like a tail wagging at the sky.
I tried to smell what I was seeing, decorating the window with nose smears. “It looks like a painting on a teapot. Are we in China?”
“Not China,” she corrected, “these are the Black Hills. I didn’t expect them to be so… rugged.”
I double checked. Mom’s supposed to be the color expert, but black was one I knew. “They’re not black, they’re white.” It wasn’t just the hills, either. All of South Dogkota was covered in white dirt. “Why didn’t you tell me it would be like this?”
“I thought this whole state was prairie,” Mom gushed in the dazzled voice that sometimes escapes when Nature gets the better of her. “Now we just have to figure out where the trails are.”

The Wagon rolled into a gas station so Mom and the Witch could come up with a plan. While Mom was distracted, I studied a billboard beside the car kennel. Four stern-looking dudes stared heroically out of the picture toward the horizon.
When the Witch’s time to hog Mom’s attention was up, I took my turn. “I recognize Walter White, but who are the other guys?”
Mom looked up for just long enough to see what I was looking at and dropped her eyes back to whatever she was discussing with the Witch. “That’s not Walter White, you knucklehead. It’s Teddy Roosevelt. Mt. Rushmore is somewhere around here. The other guys are dead presidents, too.”
“What’s Mount Rush More?” I asked. “Is that why they call it running for president? Because you have to rush? … more than the other guy?”
“I don’t know why it’s named that,” she said, too distracted by her own questions to ask the Witch to explain something that someone else was interested in. “The other guys are Washington, Jefferson, and Lincoln. If you ask me, Roosevelt isn’t in the same league, but he’s something of a local hero.”
“What did he do? Did he defeat the bad lands?” I asked hopefully.
“In a manner of speaking.” She finally put the Witch back in her lap and ordered the Wagon onto the road. “Legend has it that he was a sickly kid until the outdoor life in the Dakota Territory turned him into a macho man. That’s the legend according to him, anyway.”
“Teddy Roosterbelt is my favorite president,” I decided.
“He created the National Parks,” Mom said, ruining it.
“That monster! How dare he block off the best bits of nature just so dogs can’t visit.”
“Questionable land claims were kind of his thing.” Mom had a way of making people in history look like fools for not knowing everything she did. “He was also a bit of a bully. He used to say, ‘Speak softly and carry a big stick.’”

“That sounds like excellent advice to me. Except how can you bark softly or any other way with a big stick in your mouth?”
“He meant that he would beat people up if they didn’t listen to him.”
“But he didn’t really mean it about hitting people with a stick, right?”
“Oh, I’m sure he did. The stick itself was a rhetorical device, but he actually challenged White House visitors to boxing matches until one of them practically knocked his eye out. He’s like the forefather of toxic masculinity.”
“What’s a torcal device?” I asked to keep the conversation on sticks.
“It means the stick was fake but the threat behind it was real.”
“What a lucky coincidence that the mountain just so happened to look like those four guys!” I marveled. “Cheesology sure is amazing…”
“It’s not natural,” Mom said, like I should have just known it. “It’s a sculpture.”
“It’s only natural that people would want to remember their heroes,” I saved. “Building a country from scratch isn’t as easy as it looks, you know.”
“That’s what bugs me about it. They didn’t build it from scratch. I love their work, but it’s not perfect. Knowing that there’s always room for improvement is what makes it so great.”
“In six miles you’ll arrive at your destination,” the Witch interrupted.
“Ugh! Not again,” Mom said in a voice that sounded like she was about to barf in her mouth.

“What?”
“Look at the kiosk. There’s no one inside.”
“But look, there’s nothing blocking the road,” I pointed out.
“If there’s no one in the booth, it’ll be obvious that we didn’t pay. We’ll have no defense if I get a ticket.”
“Do they give tickets in not-America?”
“Who knows. It would be just my luck.”
“Maybe a ranger machine can help. Are machines allowed to work during the boogeyvirus?”
Mom jabbed her arm toward the front window to emphasize the point she was about to make. “There is no machi—” When her eyes followed her arm, their indignation turned to triumph. “Look, they have envelopes! Thank goodness for cash.”
Even though old-fashioned paper money was banned in most places, Mom had found a black market twenty-dollar bill in a back-alley bank machine that she was saving for an emergency just like this. She told the Wagon to stay and reached for the door.
“Don’t go!” I begged. “No one’s coming for the envelopes, remember?”
“They can’t kick us out if we follow the rules,” Mom called over her shoulder before closing the door on the conversation.

When she remounted, she stuck the Get Out of Jail Free card on the front windowsill and ordered the Wagon to giddyup. “Envelopes don’t give change for a 20, so I just paid 4 times the entrance fee,” she counted.
“What does that mean without the numbers?”
“It means we practically own the place.”
“So what should we worry about now?”
“We could agonize about whether the parking lot is plowed. Or whether there’s a camping ordinance. Or we could worry about those nasty-looking clouds over there,” Mom suggested. “The possibilities are endless.”
The car kennel was clear when the Wagon arrived. The white dirt crowded in a wall around the edges, respectfully staying off the pavement. We left the Wagon parked tidily between the lines and climbed through the muddy, stamped-down slot in the white wall where the trail began.
Since she’d already decided to follow pre-boogeyvirus tradition with the entrance fee, Mom tried to follow rules about leashes too, even though no one was around to call her a good girl for doing it. The leash jerked as Mom’s arms whipped to keep herself head-side-up on the slippery white dirt.
There was a swish and an ack behind me, and the leash jerked harder than ever. When I turned around, Mom, the Witch, and the water bottle were scattered on the ground. Half of Mom’s leg was gone, sucked into the white dirt like quicksand. Mom pulled her leg out of the ground and shook the white dirt off of the Witch. She stood up, rubbing her butt.
“Fine, fine,” she said, like she’d heard me tell her so. She unclipped the leash and I left her balancing and chopping the air.

I practiced gymnastics in the white dirt, sniffing and rolling, rolling and sniffing like I’d never seen anything so wonderful in my life. A stream sang a tinkling song to accompany my happy dance.
“Slow down,” Mom shouted.
Once I’d burned off enough of the zoomies to stay paws-side down, I came back to see what she was on about. “What?”
She looked meaningfully at the river flowing under the bridge of white dirt that we were fixing to walk on. “Just be careful. It’s melting season and we don’t know if it can hold our weight.”
“Good thing I’m not big and fat and drill-shaped like you.” I spread my weight evenly over all four paws and pranced across with flair.
Mom watched me go, baring her bottom teeth like she does when I make something look easy that she would mess up. Once I was safely on the other side, I wagged at her to show that only a drill-shaped idiot could mess this up.
Mom put one paw over the hollow part and shifted her weight one atom at a time. Below her, the water whooshed through the roomy tunnel it had bored for itself under the dainty snowbridge. When Mom’s leg stayed on top of the white dirt rather than punching through it, she switched from slow motion to fast forward and pitter-patted to my side. If we were in a movie, the white dirt would have collapsed behind her as she ran, but since this was real life, the bridge stayed the same as before except with six extra pawprints on it.
“Good girl!” I wagged.
The next adventure found us where the trail crossed the river without a bridge. “What do we do now?” I asked.

“We cross,” Mom declared.
She jumped onto a rock poking out of the water and searched for another stone to aim her next step. The next one teetered when she landed on it. She launched herself clumsily onto shore a moment before it dunked her, dragging her trailing toes through the water. I followed, easing my paws into the icy stream like I was walking on the fragilest of snow bridges.
“Good boy,” Mom said when I joined her on the far side.
“Are you okay?” I gasped, not sure if we’d just escaped death.
“Yeah. Why?”
“That was a close one.”
The river got narrower and deeper as we went upstream. We studied each crossing for traps. Sometimes, there was a gap in the deepest water where a rock was missing. Sometimes the white dirt went all the way across, and all we had to do was decide whether it was a real bridge or a decoy that would collapse mid-river. Whether there was a bridge or not, Mom crossed without hesitation.
“Be careful,” I reminded her as she walked onto the most delicate snowbridge so far as if it were made of stone.
“Or what?”
“Or your socks will get wet.”
“They’re already wet.”
“You could lose your balance.”
“So? It’s only like 4 inches deep. What’s the worst that could happen?”
Mom had never asked me why those things mattered before. She’d told me that wet socks or falling on your butt were a fate worse than death, and I’d believed her. Now I checked my own paws for signs of drowning, but they were hidden under the elbow-deep white dirt. I pulled out a paw and watched the white flakes turn into wet. Once it wasn’t white anymore, I couldn’t tell how much of the wetness came from the white dirt and how much was from the stream.
“Knowing the worst that could happen is your job, remember?” I said so Mom would feel like the foolish one. “You told me to be careful.”
“I changed my mind. I’m tired of being careful all the time. If we have to be cautious around other people, then I’m gonna throw caution to the wind when no one’s looking. Not caring about the things that most people are afraid of is an act of rebellion, too, you know.”
Hearing Mom’s bravery, the stream turned away from the trail. It wandered into the forest in search of someone less bold to harass, leaving us alone with the hills, whose pointy tips were lost in a mysterious fog.
Want to keep reading? Grab Oscar’s book, No Place Like Alone on Amazon.



















