Montana Weekend Getaway: Peaks, Pines, and Friendship

October started out with a bang. I welcomed my best friends’ newborn baby into the world—and then whisked away on a train to Montana. It was a trip I’d been planning for months with my Canadian friends, Mackenzie and her husband, Jesse, who you might remember from our Banff adventures featured in Reunion in the Rockies: Hiking, Healing, and Holding On.

Mackenzie and I first met in Lakeside, Montana 12 years ago during a missions program, and we still have friends living in the area from that time. So, we decided to make a trip of it—to reconnect with old friends, explore some of our favorite places, and, of course, sneak in a little hiking and sightseeing along the way.

On the Rails Again

The Amtrak was running late. Typical, I thought. If I’d known, I wouldn’t have dragged myself out of bed at 4 a.m.—the new departure time wasn’t until 6:30 a.m. It was cold and dark when I left my apartment, the streets eerily quiet. It felt almost unnatural to be outside at that hour.

The last time I took the train to Whitefish, I was 18 years old. What possessed me to board in the dead of winter for a six-month missions program that would eventually take me to Brazil—with a group of complete strangers, no less—is beyond me. I was sitting on that train, too scared to leave my seat. I didn’t even ask where the dining car was—surviving the 17-hour ride on a couple of Snickers bars and a small selection of songs on my iPad. Mostly, I just sat there, staring out the window at the blur of snow, wondering what the hell I had gotten myself into.

This train ride was different, though. 31-year-old Ruth felt relaxed. Confident. Excited. Fully prepared to find the dining car when necessary. Once I stowed my luggage and settled into my seat, I put in my earbuds and played Taylor Swift’s The Life of a Showgirl , which had come out that very day and felt like a treat. As the train began to move, I watched the sun rise over the flat prairie, Opalite playing through my headphones, the whole sky glowing orange.

Wild West

Late-Night Arrival, Golden Company

By the time I finally arrived in Whitefish at 10:30 p.m., the long day had caught up to me. Dinner on the train meant polite small talk with three strangers, a glass of red wine, and the slow realization that I was running on fumes. When we pulled into the station, I wasted no time grabbing my luggage and stepping off into the crisp night air—my breath mingling in the darkness. Spotting Mackenzie and Jesse’s Jeep, I made a beeline for it—relieved, disheveled, and so happy to finally be on solid ground.

We had a short drive to Lakeside, where our friends had lined up a place for us to stay—a house that happened to be empty for the weekend, as long as someone could dog-sit. Mackenzie and Jesse opted to camp in their pop-up tent outside, which meant I pretty much had the house to myself… well, me and Murphy, the golden retriever with absolutely no concept of personal space.

Somers Bay Cafe

Slow Mornings & Strong Coffee

The next morning, I slowly peeled off my sleep mask to find soft sunlight spilling across the room. Murphy, who had stayed with me all night, sensed my movement and immediately shifted—resting his head next to mine and placing a paw gently on my hand. Coffee, I thought.

I got up, let Murphy out, and started exploring the kitchen for caffeine options. I spotted an espresso machine and, after a quick Google search, decided I could probably figure it out—just slightly more complicated than my Keurig at home. The first cup disappeared fast as I curled up on the sectional in front of the stone fireplace, the house perched on a hill surrounded by tall pines. The second cup, I took my time with, savoring every sip.

Eventually, Jesse and Mackenzie stirred, and we gathered in the kitchen—sleepy but chatty—deciding to meet our friend Katie for breakfast at Somers Bay Café.

Dock Pics or it didnt’ happen
L-R: Mackenzie, Katie, & I

Plot Points & Pancakes

Katie walked in to the cafe looking exactly as she did 12 years ago—spunky, petite, youthful—but with a touch of weariness that comes from living a lot of life. We started with the usual catching-up small talk. What do you do now? Are you single? How are the kids?

How do you summarize 12 years over brunch?

After breakfast, we grabbed coffee at Glacier Perks and wandered down to Flathead Lake. We walked to the end of the dock, laughing about how we used to take “dock pics” back in the day. When the rain started spattering down at us, we quickly made our way to the car.

Later, we met up with a few more friends—each conversation looping through the same questions, the same stories. Everyone looked the same. And yet, behind the surface-level updates, we’d all gone through enormous changes—marriages, kids, heartbreaks, moves, new careers. Still, it somehow felt like nothing had changed.

I thought about my own well-rehearsed life summary:

• Lived abroad for a few of years after high school

• Moved home to be closer to family

• Got a college degree

• Became an interior designer

• Ended a long-term relationship

• Works in business, designs, runs a blog, travels when she can, and has a great community of friends

Strange, how we can condense entire chapters of our lives into a handful of sentences.

But a person’s story is so much deeper than their SparkNotes version. You catch the highlights and lowlights, but not the stretches in between—the strength it took to leave, the strength to stay, the boldness to start over, the fear of what might happen next. And all the small moments that quietly build into the big ones.

Between Highlights & Lowlights

We slept in on Sunday morning, taking our time to get ready, before setting out for Whitefish, stopping first in Kalispell for brunch at Bella Caffe.

As we waited for our orders, I found myself explaining to Mackenzie and Jesse where I was at in life. I was doing all the things I wanted to be doing—working, creating, traveling, writing, designing, socializing— yet it felt like some of my friends were on completely different paths.

“I think I just feel—”

“Like you’re falling behind?” Jesse interjected.

“Yes!” I replied, relieved he said it out loud. Sometimes it feels like the thing you’re not supposed to admit. I’m not supposed to measure where I am based on my age. And yet, I catch myself adjusting to everyone else’s evolving lives. My life has evolved too, just not in the obvious, conventional ways. Rather than being marked by marriage certificates or mortgages, my milestones have been the hard shifts I’ve made, the intensive work I’ve done to heal from deep wounds, and navigating the weight of grief along the way. Mine are milestones of survival.

In some ways, it feels like I’m really just getting started in my 30s. I’m confident I’m on the right track, content with where I am, yet I always hold space for what’s to come—managing a mix of peace and possibility.

Holbrook Overlook

Peaks, Lakes, & Local Finds

After a hearty meal and some soul-filling conversation, we continued the short drive to Whitefish, ready to kick off the day with an easy hike on Lion Mountain Trail. The weather couldn’t have been better—sunny, cool, and perfectly crisp. The trail wound gently through thin woods, opening up to glimpses of mountain peaks in the distance. Eventually, we reached the overlook at the top, where Skyles Lake shimmered below—a small, glassy patch of water surrounded by golden trees. It was peaceful, quiet, and effortlessly beautiful.

The better view, though—at least in my opinion—was from Holbrook Overlook, where we drove up to take in the sweeping view of Whitefish Lake. The water stretched out below us, deep blue and still, framed by evergreens and mountain ridges in the distance. 

Downtown Whitefish, MT

From there, we headed downtown to browse the local shops, popping in and out in search of a touristy T-shirt or sweatshirt. Instead, I ended up with a bag of huckleberry taffy. Later, we grabbed huckleberry ice cream from Sweet Peaks and wandered along the rocky beach near the lake.

Après Evenings & Supermoons

The day stretched into late afternoon, and we checked in to Après Whitefish. Just outside downtown, the boutique hotel exudes a vintage-Montana vibe—minimal, cozy, and effortlessly cool. I especially loved the tiny A-frame sauna tucked behind the hotel, right next to a large fire pit.

Outdoor sauna behind the hotel

“We will be having a fire later,” I announced to Mackenzie and Jesse. We couldn’t not. After regrouping at the hotel, we headed to Blackstar for dinner—a multi-level spot with natural materials and a color palette inspired by historic train cars, nodding to the town’s railroading history. I ordered the Pizza Night, washed down with an Oktoberfest beer. Busy for a Sunday, yet the atmosphere felt warm and familiar, like families gathering before the start of a new week.

As we made our way back to the hotel, we spotted the moon looming grandly in the darkening sky.

“It’s a supermoon,” I informed my friends.

“What does that mean?” they asked.

“I don’t know… it just appears larger and brighter than a typical full moon,” I replied. I casually track the phases—in the most non-weird way. There’s something endlessly fascinating about the moon, and I am drawn in by her strong magnetic pull. I love that there are cycles, changes… chapters.

Supermoon

Embers and Departures

We did, in fact, have a fire, thanks to Mackenzie’s absolutely superb fire-making skills. I sipped my huckleberry beer and enjoyed the warmth as we all huddled close. Just as we were about to process our weekend together on our final night, some hotel guests wandered up to share in the fire’s glow. They’d just returned from Banff, so we had that to talk about. Not that we were in the mood for conversations with strangers, but it was nice nonetheless. It dawned on me, though, that our chat mostly revolved around work and where we live—echoing the same small-talk we’d had with our friends in Lakeside.

The couple eventually left for bed, wishing us safe travels home. We watched the fire slowly dwindle, its glowing embers drawing their last breaths—shimmering and winking like stars above, soon to fade into the darkness.

Whitefish River

Mackenzie, Jesse, and I parted ways at the Whitefish train station the next morning—them heading north back to Alberta, me east to North Dakota. Promising each other we’d plan our next trip soon.The weekend had given me much to think about, and thoughts swirled through my mind as I boarded the train.

The Long Way Home

This trip wasn’t exactly what I expected. I thought I might catch the spark of youth again—the rush of change, the novelty that once made this place feel so special. But time has a way of testing the strength and longevity of friendship. I expected the reunion with our Lakeside friends to feel more emotional; after all, we’d spent six intense months together navigating a foreign country in our formative years. Maybe I hoped to rekindle a connection that had quietly faded over time. Instead, on the train and later around the campfire in Whitefish, I found myself having the same conversations with strangers as I did with old friends—Where do you live? What do you do? Married or single? I struggle with small talk, but I understand that sometimes that’s all there’s space for.

Misty Mountain Morning

And yet, I’m not disappointed.

There’s a line from the movie, Before Sunset: “I guess when you’re young, you just believe there’ll be many people with whom you’ll connect with. Later in life, you realize it only happens a few times.”

It rings true for me. I have a handful of people with whom I share a truly meaningful connection. I feel deeply grateful for this little pocket of people—gems both near and far. Some we talk every day, some once a month, and with others, like Mackenzie, we can pick up right where we left off after years. Whether they’ve been around for the highlights, lowlights, or the long stretches of miles in between.

As the train hummed along through mountains and mist, I fought off the early-morning drowsiness—afraid that if I closed my eyes, I’d wake to flat prairie land again and find it had all been a dream. The novelty of youth may have faded, as the years carve deeper grooves in us like rings on a tree trunk—marking the passage of time and the seasons we’ve survived. But these mountains—this place—will always be magical to me.