Dennis Hill Lower Loop: A Fall Walk with Mom and Three Nervous Puppies
My mom called the other day with a simple question: "Want to go for a walk with me and the pups?"
With Portugal just days away, I'm trying to soak up time with family before heading overseas. Easy answer—"Yeah, Mom, let's do it."
We packed up the three sister pups and rolled over to Dennis Hill State Park in Norfolk, Connecticut. This lower loop has become one of those trails I keep coming back to. Not because it's dramatic or challenging, but because it delivers exactly what I need—quiet woods, manageable distance, and enough interesting features to keep it engaging.
The Parking Lot Promise
Pulling into the lot, we knew we'd made the right call. Late afternoon sun was hitting the leaves in that specific fall way that only happens for a few weeks each year. The air had that perfect temperature split—warm enough to be comfortable, cool enough to feel like autumn. Leaves drifting down. Acorns too, which would become more relevant shortly.
But first, the puppies had to freak out.
These three little dogs—all sisters, together since birth—do not understand cars yet. The short drive from home to the trailhead might as well be a cross-country expedition based on their anxiety levels. One pooped. One puked. Classic.
With some TLC and reassurance, they calmed down enough to hit the trail. Honestly, the puke-and-poop routine is becoming their signature move. More on that later.
The Dennis Hill Lower Loop Experience
Dennis Hill State Park offers two main options—the lower loop and the climb to the pavilion on top. We stuck with the lower loop, which winds through the woods at a comfortable pace without any serious elevation demands.
The trail pulled us in immediately. Sun filtering through the canopy, hitting different than it does in summer when the leaves are thicker. Fall light has this quality that makes everything sharper, more defined. Mom and I fell into an easy pace, talking about life while the pups investigated every interesting smell along the trail.
Then the acorn storm hit.
I'm not exaggerating—the wind picked up, and suddenly we were in an acorn hailstorm. Must have been a hundred of them raining down, bouncing off the ground with that distinctive crack-crack-crack sound. Nearly got hit a few times. The pups didn't know what to make of it.
One of the sisters was having the time of her life, running around like she'd discovered the secret to unlimited energy. That's what I love about watching dogs on trails—pure joy, no self-consciousness, just full commitment to being alive in that moment.
These three stick together constantly. Being sisters who've never been separated, they move as a unit—exploring, checking in with each other, staying close. Small, loving, completely bonded. Watching them navigate the trail together makes the whole experience better.
The Lower Gazebo
The trail weaved on, eventually depositing us at the small gazebo overlooking the valley. There's a larger pavilion up on Dennis Hill's summit, but the lower gazebo stays quieter. Most people either skip it or push on to the top.
We sat, caught our breath, talked about whatever came to mind. Gave the pups water. Picked a few ticks off them—fall doesn't eliminate tick season entirely, just reduces the odds. The valley stretched out below, that classic Connecticut hill country view of rolling terrain and scattered farms.
These moments before international travel hit different. You're about to spend weeks in unfamiliar territory, dealing with logistics and adaptation, so sitting in a familiar spot with your mom and three small dogs feels like something worth holding onto.
After enough rest, we headed back down the trail toward the car. The walk back matched the walk in—calm, comfortable, exactly what an afternoon hike should be.
The Car Ride Home (Round Two)
Then the puppies freaked out again.
Same routine. Puke and poop. Sigh.
You pet them, tell them it'll be okay, give them love and reassurance. But still—why, little friends? Why the puke and poop every single car ride?
They're young. They'll figure it out eventually. Or they won't, and car rides will always involve cleanup duty. Either way, they're good dogs.
Why This Hike Keeps Working
I've written about Dennis Hill multiple times because it keeps delivering despite—or maybe because of—its familiarity. It's close to home. The pace works for casual walks. It stays quiet and reserved compared to more popular Connecticut trails. And it's interesting enough to not feel repetitive.
Not every hike needs to be an epic adventure. Sometimes the best outdoor experiences are the ones that fit easily into normal life—an afternoon walk with your mom, three nervous puppies, and an unexpected acorn storm.
Fall in Connecticut creates these perfect windows when the weather cooperates, the foliage shifts, and the trails feel completely different than they do the rest of the year. Dennis Hill's lower loop captures that seasonal shift without demanding major time or effort.
With Portugal approaching—the Fisherman's Trail, coastal hiking, multi-day distances—these local Connecticut walks serve as both preparation and reminder. The big trips are great, but so are the small ones close to home with the people and pups who matter.
Hiking with my mom in the fall, watching three sister dogs experience the woods together, getting caught in an acorn rainstorm—this is the kind of memory that sticks around.
Even if the puppies keep puking in the car.
Books by Tim Mack
The Last Train: 46 Days with the Final Ringling Brothers Circus
In April 2017, I left my Atlanta circus company to join the final tour of Ringling Brothers and Barnum & Bailey Circus—"The Greatest Show on Earth" closing after 146 years.
The Last Train captures the last 46 days of an American institution from inside the legendary mile-long circus train. Experience the brutal 12-hour setups, the international community of 300 performers from over 30 countries, and the bittersweet reality of giving everything to something that's ending.
From lion encounters during load-out to watching America roll by from train vestibules, from emergency breakdowns to the emotional final bow at Nassau Veterans Memorial Coliseum on May 21, 2017—this memoir preserves how the world's most famous circus actually worked, and what it meant to the people who lived it.
Paperback – August 23, 2025
The Secret to 7-Figure Living: How to Open Your Life to Boundless Joy, Prosperity, and Freedom
This book redefines prosperity and success beyond superficial wealth, instead measured by intentional cultivation of creativity, adventure, strong relationships, and purpose.
Key concepts include:
- Prioritizing life experiences over material accumulation
- Embracing minimalism to create space for deeper connections
- Generous living with time, skills, and focus
- Choosing quality relationships over quantity
- Designing environments that spark inspiration
- Aligning actions with values-based goals
- Leaving meaningful legacy through everyday choices
The book provides a blueprint for cultivating happiness accessible to everyone willing to redefine affluence on their own terms, regardless of financial constraints.
Paperback – February 12, 2024
Continue following the journey at RoamingSparrow.com - where adventure meets authentic storytelling.
You can check out this post and your own profile on the map. Be part of the Worldmappin Community and join our Discord Channel to get in touch with other travelers, ask questions or just be updated on our latest features.