Some weddings unfold exactly as planned. And some ask everyone involved to dig deep, pivot fast, and trust that what matters most will still find its way through.
This was the latter.
Last September, Plus the Pups had the privilege of supporting Jamie, Christian, and their rescue girl Shiloh for their full wedding weekend at Flying Diamond Ranch in Steamboat Springs, Colorado. It is one of the most beautiful venues we have ever worked at. It is also one of the most unpredictable when Colorado’s mountain weather decides to make itself known.
This is Shiloh’s story. It took over a year to share it, not because anything went wrong, but because some days take time to fully understand what they taught you.
Meeting Shiloh: Where It All Started
When Jamie first reached out to Plus the Pups, there were tears on the very first call. Not unusual in this work, actually. The couples who find us are the ones who love their dogs so deeply that the idea of leaving them out of their wedding feels like leaving a family member behind. Jamie was that person completely.
Shiloh is a rescue with a tender heart and real anxiety. She takes daily medication to help her move through the world, and summer storms are her kryptonite. Jamie had a lot of feelings about that, about Shiloh’s needs, about whether including her was the right call, about wanting to do right by her dog on such a big day. Part of this work is holding space for all of that without judgment. Jamie was doing everything she could for Shiloh. That is all any of us can do.
For the meet and greet, we met at the park outside Jamie and Christian’s old apartment building because it was a place Shiloh already loved and felt completely safe. We walked together, watched how Shiloh moved through the world, how she greeted other dogs and strangers passing by. Jamie and Hollie hugged and cried some more about how much they love their dogs. It was one of those moments that reminds you why this work exists.
From the very first conversation, Shiloh’s comfort was the priority. Everything else was secondary.
“When Jamie and I first connected, we both cried over our shared love of our dogs and the commitment to making sure they got what they needed. That is the foundation every one of our weekends is built on.” — Hollie, Founder of Plus the Pups
Thursday: The Drive to Steamboat
As the wedding weekend approached, Jamie let Hollie know that the truck would be packed full of wedding items and there simply was not room for Shiloh on the drive to Steamboat. Could Hollie drive to Denver first to pick her up before heading to the mountains?
Obviously, yes. That is what a full-service concierge does.
Shiloh and Hollie made the drive together, checked into the hotel, got settled, and spent the evening decompressing. There is something about those quiet hours before a wedding weekend that matter more than people realize. It is the time a dog gets to exhale, to understand that this new place is safe, that this person with them is trustworthy. We never rush that.
Later that evening, Jamie and Christian wanted to see their girl. So Hollie brought Shiloh to meet them for a late lunch at Braid and Beard. The three of them sat together, Shiloh included, and it was a genuinely sweet moment in the middle of what was about to become a very full weekend. It is something we do not talk about enough: how much time a wedding concierge actually spends with a couple one on one, and how important it is that you genuinely connect with the person you are trusting with your dog.
Friday: The Rehearsal and the Welcome Party
Friday morning was easy. Shiloh was regulated, well-rested, and settling into the rhythm of the weekend. Hollie drove her to Flying Diamond Ranch for the rehearsal, giving her time to experience the property without the pressure of the wedding day. This is always one of the most valuable things we can do for an anxious dog: let them meet the space before the space is full of people and emotion.
That evening, weather permitting, Shiloh was scheduled to greet guests at the entrance of the welcome party at Icehouse. And she did. She was happy, calm and doing so well.
Everything was perfect. The skies were clear. The weekend was unfolding exactly as planned.
And then wedding day arrived.
Saturday: When Everything Changed
Shiloh felt it before any of us did.
The weather shifted fast on wedding morning, the way Colorado mountain weather does when it decides to remind you who is in charge. The anxiety that Shiloh carries quietly on calm days came to the surface hard and fast. She was scared. Really scared. The outdoor ceremony that Jamie had dreamed of was suddenly in question, and Shiloh was curled up in the wheel well of Hollie’s car with the heat blasting, the one place she had decided felt safe.
The vendor team communicated in the rain with zero service on site. Everything changed by the minute. And everyone rose to meet it.
We squeezed in first looks before the rain hit. Shiloh had her moment with Jamie and Christian in the aspen grove, that gentle exhale of recognition when your dog sees your face and everything softens. Her medication had been carefully timed around the day’s schedule: one gabapentin before leaving the hotel, a second around 3pm so it would be fully active for the ceremony. We had a plan. And then the plan changed. And then we made a new one.
When the ceremony time came, we created something that honored both Shiloh’s safety and Jamie’s dream of having her there. The owner of Flying Diamond Ranch drove Shiloh and Hollie straight to the tent entrance in her 4×4. And through the car window, the moment Shiloh saw her mom, both of their bodies softened at the same time.
She walked down the aisle. Calm. Brave. And then she went straight back to the car where she felt safe, which is exactly where she needed to be.
What This Day Taught Us
This was one of the hardest wedding days in the history of Plus the Pups. Not because anything went wrong. But because it was emotional and unpredictable in the way that asks you to dig into your instincts and trust them completely, even when the plan is dissolving around you.
It taught us how to stay grounded in absolute chaos. How to advocate for a dog’s well-being when everything is shifting. That a strong, communicative vendor team matters when you have no service and the timeline is changing every ten minutes. How to choose safety over aesthetics every single time without hesitation.
It also reinforced something we already believed but felt more deeply after that day: our dogs feel everything. The energy of a room, the shift in the weather, the emotion of the people they love most. Shiloh knew before any of the humans did that the day was going to be hard. She spent it being honest about what she needed, and our job was simply to listen.
This work is so much more than holding a leash. It is reading energy and making real-time decisions as well as compassion and fast thinking and presence. It is staying calm so the dog can borrow your calm when theirs runs out.
Nothing unfolded the way anyone imagined. And Shiloh still walked down that aisle.
“Crying. Us and Shiloh are so lucky to have had you to support her with the most personalized and intentional care. You made our dreams come true while protecting our sweet baby. Forever and ever grateful for you and this entire team.” — Jamie and Christian
About Flying Diamond Ranch
Flying Diamond Ranch is one of the most breathtaking wedding venues in Colorado, and one we hope to work at again and again. Nestled in the mountains outside Steamboat Springs, it offers the kind of wide open space and natural beauty that makes couples drive hours to get married there.
For dogs, the wide outdoor spaces and natural environment are a genuine advantage. There is room to walk, room to decompress, and room to find the quiet corners that an anxious dog needs. The team at Flying Diamond was extraordinary on Shiloh’s wedding day, stepping in with their 4×4 without a second thought when the plan changed. That kind of venue partnership is everything.
If you are planning a wedding at Flying Diamond Ranch and want to include your dog, we would love to be part of your day.
Frequently Asked Questions
Yes, with the right preparation and support. Anxious dogs benefit enormously from consistency across a multi-day experience: the same caregiver, familiar routines, carefully timed medication if prescribed, and a plan that prioritizes their comfort over the schedule. The Wedding Weekend Experience at Plus the Pups is specifically designed for dogs who need that continuity. We get to know your dog before the weekend begins, build a custom itinerary around their needs, and make real-time decisions on the day when things shift.
We always plan for this. Part of what we do before every wedding weekend is build contingency plans for weather, especially for dogs who are sensitive to storms. We monitor conditions, we communicate with the vendor team, and we make real-time calls about what is best for the dog. Sometimes that means your dog spends part of the day somewhere safe and quiet instead of in the middle of the celebration. That is not a failure. That is the plan working exactly as it should.
We follow the couple’s instructions and their veterinarian’s guidance precisely. Before every wedding we receive detailed medication and feeding instructions from the couple, including timing, dosage, and what to do in unexpected situations like a sudden storm. We have administered gabapentin, sertraline, and xanax under veterinary guidance at weddings. Your dog’s health and safety is always the first priority, and we are comfortable adapting the plan in real time when their needs shift.
The Wedding Weekend Experience includes full concierge coverage for every meaningful event across your wedding weekend: rehearsal, welcome party, the full wedding day, and a post-wedding send-off activity, plus two nights of overnight care. One dedicated team member is with your dog for the entire weekend. For destination weddings, we always arrive a day early to ensure we have bonding time with your dog before the wedding day begins. All travel logistics including dog-friendly accommodations, flights if needed, and car rentals are covered by the couple. Everything related to your dog is covered by us. Read more about our services here.
Yes. Flying Diamond Ranch is a venue we know well and love deeply. If you are planning a wedding at Flying Diamond and want to include your dog, we would love to hear about your vision. Reach out and let us know about your dog, your date, and what you are imagining for their weekend.
Planning a wedding weekend in Steamboat Springs or anywhere in the Colorado mountains and want your dog there for all of it? Read about how we work.
Or reach out directly and tell us about your dog and your vision. We would love to be part of your story.
Plus the Pups is a bespoke wedding dog concierge service based in Colorado, with a team serving couples across the country and beyond. Founded in 2022, we have been part of more than 140 weddings, from intimate mountain elopements to full destination wedding weekends. Our team handles every detail so you can be fully present on the most important day of your life, knowing your dog is in the best possible hands.
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