Whitefish, MT

Although I had never heard of Whitefish until embarking on the Goldilocks Project, I was recently told to think of Whitefish as a “mini Jackson, WY.” Upon hearing that, I was less interested, since post-Jackson I declared that resort towns were going to be off the list, but I was still willing to give it a few days time, if for nothing else than for project completeness.

Maybe it was just that we were there in the least touristy time of year, but Whitefish felt very residential to me, and the costs of homes and shopping costs were not unreasonable. I expect that within the decade Whitefish will become outrageous but was surprised it hasn’t yet. It’s between two large lakes (Whitefish Lake and Flathead Lake, downtown is 8 miles away from the ski area, and Glacier National Park is less than 45 minutes away. Despite feeling remote, there is an international airport with approximately a dozen cities (including Seattle) that are directly serviced, and the larger city of Kalispell is within a half-hour drive.

That said, I don’t think you need to visit Kalispell on a regular basis, and it’s not like Kalispell is a huge metropolis (it’s only a population of 26,000). Whitefish has everything we’d need for day-to-day living: gas stations, grocery stores, and cultural/entertainment-type events. There’s also a good ice cream shop (Sweet Peaks – the same shop we ate at in Missoula), multiple bakeries (I really enjoyed Fleur), and tons of restaurants (we ate at Blackstar, which was not my favorite but I also think I ordered the wrong meal for my mood).

The Good

• Felt like a friendly, happy, and tight-knit community. We were there for Halloween and got to watch all of the families trick-or-treat at the downtown businesses.
• Really well located for all of the things we like to do. I especially like the proximity to Glacier National Park, but that's just a bonus to the neighboring lake and ski area.

The Bad

• Likely excessively touristy in the summer and winter months. It was clear that many of the businesses were set up to handle huge amounts of customers, which makes me think it’s pretty difficult to avoid crowds most of the year.
• Per the employee at Stumptown Snowboards, winter stays pretty drab and gray. It keeps the snow fresh, but definitely is not great for someone like me who suffers from SAD (seasonal affect disorder).
• Food was mediocre. In another setting it would have been good, but it felt like it was catering large touristy crowds rather than focusing on top-notch dining. 

The Verdict

Maybe. There wasn’t anything that would lead to an immediate “no,” but I think there are other places on the list that I like better. Being in the same state makes it easy to compare Whitefish to Missoula, and ultimately I think choosing a small city like Missoula is a better compromise for the full-picture lifestyle I’m hoping for.

This whole section of Montana is full of larches – the "evergreen" trees that turn yellow in the fall.

Glacier National Park is only 45 minutes from Whitefish. Unfortunately, the Going to the Sun Road, the main scenic route, was closed, so the hike we chose was not the most stunning, but still beautiful. 

It was hard to gauge what type of community activities go on around town. We were there for Halloween, and there was a lot of holiday focus, but I didn't see any indication that there were other things that happen on a regular basis.

It was unclear if any neighborhoods were opening up to trick-or-treaters, but downtown sure was popping with then! 

We had dinner at Blackstar, which was fine, but it was clearly laid out to serve large post-skiing crowds. 

The permanent sidewalk art around town was really cute!

The buildings around downtown had the same boxy style that I've been associating with the northern ranching states. 

Fleur was the tastiest bakery we've ate at in a while, and based on the conversations we overheard it did seem to cater to locals more than other eateries in town.

Although thought of as a skiing destination, Whitefish Lake is beautiful and likely brings in its own fair share of summer tourism. 

Although hard to read, these were a hoot to read, but also a bit of a turnoff. Not only did it emphasize that Whitefish survives on tourism, but it seemed to imply that it's almost impossible to live in town unless you work 3+ jobs.

Missoula, MT

From the beginning, I had a not-so-secret hope that Missoula would be a top contender. I visited Missoula for a two-day work trip about five years ago, and came back announcing I was going to start the hashtag, #movemetomissoula, and you know I love the narrative of this little long-ago meet-cute for our final destination. 

The drive across Montana was stunning, but started to feel more hilly rather than mountainous as we approached the city. I do use the term "city" intentionally. This was the first spot so far that was a true stand-alone city, albeit small – not a stand alone town or a quaint suburb. There were the standard pros and cons of a city: more diversity, higher-end stores, and a noticeable homeless community. Unlike most cities, Missoula is surrounded by an abundance of accessible public lands. 

Cameron and I made use of the shopping available: he bought some new running shoes, I found a ceramic planter for our air plant (inside a boba shop to boot!), we enjoyed Sweet Peaks Ice Cream, and Top Hat for dinner. As it was the Saturday before Halloween, many of our fellow diners were in primo Rocky Horror Picture Show attire. We also did a little walk along the Bitterroot River and hiked the "M" trail overlooking the University of Montana campus. Many parts of Missoula made it very clearly a college town, but we didn't find as many cheap student haunts as I would have hoped. That is, until our drive back through on the way home, where we found the more run down and affordable student-focused part of the city.

The Good

• Small-city charm and amenities, such as cultural events, entertainment, and a really close airport.
• Lots of outdoor options, in and out of town. From the top of the "M" trail, you can see the whole city, which has a hearty distribution of trees and is fully surrounded by hilly pine forests. 
• Some exceptionally cute shops. Oddly, the artwork sold inside of Pearl Boba was my favorite. 
• Two sections to downtown – the main downtown area that is relatively upscale, and then the student-focused areas across the river, known as the "Hip Strip."
• A great trail system, including many riverside paths.
• Diversity in all senses of the word. As far as economic diversity, we could (probably) afford the type of property we'd ultimately be looking for. 

The Bad

• Lots of casinos nearby. It doesn't bother me too much, and we even spent a night in the parking lot of the Gray Wolf Casino, but Cameron finds them off putting. 
• Football-heavy focus for the college, and around town in general. 
• A noticeable population of folks who were homeless and likely would benefit from social services, if they were available. To decrease the impact of this negative, I did see one business front that clearly existed for that purpose. 
• Per a former long-time resident, some winters days can feel very short (it is at a high latitude) and summertime smoke can be oppressive for weeks. 

The Verdict

Yes. Honestly, I couldn't think of anything that Missoula lacked, except the giddy excitement I want to feel, and that I think I did feel during my first introduction to Missoula. Perhaps I put too much pressure on this visit and my expectations outran reality. However, we got to come back through Missoula approximately a week after the "official" visit. Whereas the first days were warm and colorful, visit #2 presented the surrounding hillsides in a heavy dusting of snow. Despite the near-freezing weather and graying skies, the excitement began to grow. I guess what I'm saying is, don't be surprised if I announce next year that Cameron and I are moving to Zootown. 

Birdseye view of the city from the top of the "M" Trail. You look down directly at the university campus, but can see all of the surrounding hills and mountains (most of which are national forest lands). Although not pictured, off to the right you get peek-a-boo views of a nearby sk

This manmade surf wave on the Clark Fork River is in downtown and nestled next to Caras Park. It's what initially won me over five years ago. 

"No Hate in our State" was one of many slogans I saw posted on business widows. Other common ones were "Black Lives Matter" and "Shop Small Missoula." I took them as a positive sign.  

There was so much going on! Live music, plays, Halloween events, running races, and surely many others that I didn't pick up on were advertised around town. And of course, there's the seemingly mandatory "Griz Country" sign in the top corner of this window.

Look at all those green park spaces on this map! 

Pictured in the map above is the Clark Fork River, and this is the Bitterroot River. We drove by some houses for sale along this river, and I couldn't help but visualize floating down it in the summertimes. 

When we returned to Missoula about a week later, it was definitely grayer and some snow was lingering on the ground. Nonetheless, I thought the neighborhoods were ideal and many had mixed-home options. 

Once we found the Hip Strip, I knew there was enough college grunge to be fun!

The college side of town is where all of the good cheap food is. I got a mega burrito for $8.

Per the internet's recommendation, we also stopped in for a Veera doughnut, despite being stuffed on $8 burritos. 

Sheridan, WY

I really wanted to like somewhere in Wyoming. I like that Wyoming is "the equality state" (they were the first state to elect a woman governor), and I like the slogans "that's WY," "Wy Not?," and "square but fun." Although Sheridan was not on the original list, it seems like it was the nice in-between compared to what towns were we had already visited so I'm very thankful we had occasion to stop and visit some family. 

Sheridan's park and trail systems made the first good impression, and Main Street was popping! I was on the quest for some nice bread, which I found at a specialty wine and grocer just off of the main strip. All around town were metal statues, with a range in themes. Although largely cowboy-focused, there were plenty others, including three cheeky monkeys, that caught my eye. 

Our family (on Cameron's side), feel like they live in a rural neighborhood, and they have enough land for horses, yet they were only 10 minutes away on an easy road. Plus, it sounds like they can ride said horses into town via a hilltop trail. I wondered aloud if I would need to adopt cowboy culture, but they assured me that wasn't necessary to fit in. Cameron's cousin also emphasized that the town had a healthy percentage of remote workers (like us!) and heirs from well-known companies (not like us, but still interesting) that were contributing to the local economy, rather than detracting from it.  

The Good

• Active community, both in the sense that people are sporty/outdoorsy, but also that they are contributing members of their community. 
• Lots of town culture. I was bummed we'd be missing the post-Halloween pumpkin smash. 
• Large and well-maintained trail and in-town park system. 
• Safe, family-focused community that seems like a great place to grow up as a kid. Cameron's second cousin has a variety of activities he does (4H, hockey, STEM, soccer...), and per his mom, they're heavily subsidized by the community. 
• Although seemingly isolated, Sheridan has everything you would need, including basics like Walmart and an airport, while still having room for local and higher-end businesses to thrive.
• A sector of our family lives nearby, and although I've only recently met them, I have the feeling they'd be good family to live close to. 

The Bad

• It seems like a big enough community that we would find our niche, but as liberal non-ranchers I expect we'd be in the minority. We were listening to Wyoming Public Radio and it was clear the values of the community (ensuring elementary school students are eating locally raised beef and that the warmer autumn is making elk hunting more challenging) are outside of my general interests. 
• Virtually no diversity. This relates to the above comment, but I did not see a single non-white person. 
• There is a lot of outdoor recreation in the nearby vicinity, but big downhill skiing is relatively limited. Antelope Butte is nearby, and meets my minimum skiing requirements, but it's definitely less than ideal. 
• Like most of Wyoming, the immediate surroundings are largely grassy/shrubby hills that give the impression of being desolate and inhospitable, although there were more trees in Sheridan proper than we'd seen in most of the rest of the state.

The Verdict

Maybe. I want to do some further research about why Sheridan didn't make it onto my original list, and assuming nothing awful comes up, I'd like to revisit with a more discerning eye. Luckily, I think we'll have the excuse to re-visit the family in the not-so-distant future. 

We spent the night before Sheridan in the nearby National Forest. The sunrise on semi-snowy roads was pretty, but the surrounding landscape is barren-looking grassland.  (Sorry for the wet spots on the window shield; we were frozen in that night!)

This historical(?) thatch roof building within a large park complex was my first tip off that I might like Sheridan. 

Another tip off was all of the kids playing outside (and the blue waterslide in the background). 

The cowboy motif was prominent, but not necessarily off putting. 

The cowboys were offset by some other humorous art, including these cheeky monkeys. 

Downtown was full of cool looking buildings filled with all of the things I look for: interesting shops, varied restaurants, quirky art, and people! 

I didn't recognize whoever was playing at the Wyo Theater while we were visiting, but it looked like there was an ongoing lineup. 

I was bummed we were going to miss the post-Halloween pumpkin smashing. We also missed the weekly farmers market and the monthly art fair. 

In addition to the parks and trails, the river appears to be well used for summer rafting. 

I expect this seasonal ice cream stand also is well used in the summer. Although not pictured, many of the buildings and shelters within the parks advertised that they were paid for by an optional 1-cent tax. I appreciate seeing tax dollars at work. 

Buffalo, WY

Going in, I was amped for Buffalo. The drive through Wyoming was pretty, and Cameron's dad, virtually unprompted, was talking about how much he liked Buffalo when he biked through (albeit a few decades ago). From the drive in, I knew a snowy pass with recreation options was nearby and per the town's tourism website, I knew there was going to be a charming historic downtown.

The day we arrived, we treated ourselves to a paid campground for their showers and laundry services. The morning was brisk and frosty, but yellow leave were falling and I felt clean and fresh – a great start for this town to make a good impression. 

While there, we worked from City Park, and ate dinner at the Virginian. I also spent some time walking through town and some neighborhoods, and stopped in an outdoor supplies shop (the Sports Lure), a thrift store (GiGi's Vintage and Upscale Resale), and a local art gift shop (Wyoming in Color). All were nice, and had degrees of small-town charm, but it was obvious that everyone I interacted with knew I was an outsider. I don't know if it was just the time of day, or the tight-knitness of the town, or my yellow corduroy pants, but I could tell I was not blending in. 

The Good

• Historic downtown with character and some seemingly long-standing businesses. 
• Close proximity to Bighorn National Forest. We spent a night there, and it seemed like there were lots of hiking trails and likely snowmobiling access in the winter. 
• The in-town trail system parallels a pretty creek and has direct access to the national forest. 

The Bad

• Very limited amenities in town. It seemed like if you wanted anything more than a limited local grocer, you'd be driving at least 35 minutes. 
• Felt like a locals-only vibe. I think all of the store owners recognize the economic value of tourism, but I didn't feel like I'd be welcomed if I moved there. 
• Per Cameron – too dry and shrubby, despite being able to see snow-capped hills nearby.
• When looking for a place to eat, only ~20% of the nearby options were opened on a Wednesday night. Maybe the town is popping on the weekends, but weekdays are pretty bland. 

The Verdict

No. It was hard to not compare to Jackson, WY given the proximity of our visit, but whereas Jackson was far too bougie, Buffalo was not bougie enough. I'm not against a remote town, but Buffalo didn't have enough on the good side to counteract the challenges that there would be. 

Per the town's website, they are unsure if Buffalo is named after the animal or the town in New York. As an outsider, it seems far more likely that it's named after the animal.

There were lots of murals around town and they all seemed to boast odd facts and slogans that made me giggle. This one reads "more than a one horse town"...

...and this one: "a creek runs through it."

The main town square is named "Crazy Woman Square." I thought that was simultaneously funny and rude, but then we started so see more spots and shops around town boasting the Crazy Woman nomenclature. Turns out there is a nearby creek and canyon that bears that name.

It seemed like Clearwater Creek was the primary selling point for the town. It was nice, and the parallel trail took you into the national forest. 

Maybe it was the time of year or the time of the week, but downtown seemed pretty lifeless, despite the historic charm it seemed to boast. 

The town notice board advertised some upcoming events. A showing of Rocky Horror Picture Show is a plus in my books, and, although not pictured, another flyer I saw nearby was for a weekend fall arts and crafts and crafts fair. 

All of the statues in town were historic in nature. I prefer a bit more whimsy, but I suppose this one's proof that it's more than a one horse town. 

Frank Prosinski Park, where we hung out most of the day, was nice and relatively-well attended, albeit mostly by retirees walking their small dogs. 

We parked next to a fenced-in horseshoe lawn, so Pancake got some unleashed outdoor time.