Our Held at Gunpoint Top Ten Best Towns

Jason

Dec 7, 2014 — 8 min read

If someone held a gun to our head and said pick a place to live now, there are a few places that immediately pop into our heads. Our top ten best towns of North America are places we would consider living should we ever decide to stop traveling (but why would we want to do that).

The cities and towns we’ve chosen are NOT in an order of any kind since that would take loads more critical thinking, and alcohol, and since we’re not planning on stopping our perpetual travels we just don’t want to invest that kind of energy.

Now here is the big disclaimer: We are NOT including the Best National Parks in this top ten because we can’t live year round inside Yellowstone NP or The Great Sequoia NP; we’re NOT including Our Favorite Small Quirky Towns like Idyllwild, Marfa, Trinidad, Mt. Airy, etc. While we love visiting certain cities like Chicago, Portland, Seattle and San Diego; we’re only choosing towns that both of us want to live in. So, some of my favorite places to visit such as Lake Havasu City or Palm Springs didn’t make the cut; we’re only featuring towns that we’ve visited since we’ve been on the road full-time so places like Sayulita Mexico, Sweden, Switzerland, or Puerto Rico didn’t make the list. Ok, I think that pretty much covers it.

Below we’ve listed our Top Ten Best Towns that we feel most represent our lifestyle, enjoy.

The past several years have been good to Asheville, North Carolina garnering them accolades from news outlets to retirees to hipsters, it seems everyone wants to live in Asheville; but with a population under 90,000 it’s still a small city. There are loads of outdoor activities (which is important to us) from white water to foraging, a crazy awesome local food scene, and a whopping 17 local breweries and counting.

Our Bests: Chocolate at French Broad, Cider at Urban Orchard and a crazy good Gluten Free restaurant called Posana. To see more on this town, click the links below:

The population of Bend, Oregon sits around 80,000 and the climate is transitional where the Ponderosa Pine Forest meets the High Desert, so temperatures are fairly mild and rainfall is nowhere near the levels of the more western towns. Winter adventures are a short drive away in the Cascade Mountains while summer months provide loads of paragliding, rafting, and mountain bike trails to conquer. There are 19 breweries in Bend (26 if you count the surrounding area) and plenty of great people to raise a glass with.

Our Bests: Unique ales at Crux Fermentation Project and a killer smoked salmon pizza at Jackson’s Corner. To see more on this town, click the links below:

Charleston, South Carolina is the perfect melting pot of hipster hangouts, European sex appeal, southern charm, history, and don’t forget the ocean is right there too! We stayed in the Francis Marion National Forest and came down to visit the city 3 different days and we just couldn’t get enough! With a population around 130,000 it’s a little larger than we prefer but it’s really hard to beat the friendly people and the killer food.

Our Bests: Get lost on the cobblestone streets downtown and when you’re hungry wander into any of the tiny restaurants tucked away in residential streets or head over to SNOB (slightly north of broad), you won’t be disappointed. To see more on this town, click the links below:

Charleston, South Carolina – Is this Europe

I know we said no big cities but we couldn’t resist one of our favorite Canadian places (granted we didn’t visit in winter so maybe our dreams would be shattered after a day or two of frigid temps). However, we wouldn’t live in the city, we would choose one of its smaller, more quaint neighboring towns. Just outside of Toronto is Niagara Falls, Burlington, Waterdown, Prince Edward County and the Great Lakes all of which we fell in love with for different reasons. Now back to Toronto…the city is full of history yet it’s all new and shiny at the same time. Toronto Island is a fun little tourist trap, and we happened upon a nude beach which is always good and awkward (when you are fully clothed).

Our Bests: Pure Spirits Oyster House and Grill and a Fritter from the Brown Dog Coffee Shoppe (Waterdown). To see more on this town, click the links below:

Lots of MI is awesome but the gem of this state has to be Traverse City! Famous for cherries blah blah blah; what this town knows is Beer, Wine and Cider! With a population of 15,000 people it’s a small town that packs a HUGE punch! We could have spent months exploring all the local eateries, coffee roasters, bakers, food trucks and booze crafters. A short drive up the Leelanau Peninsula or the Old Mission Peninsula put us deep in the heart of MI wine country, not a bad way to blow through a few days.

Our Bests: Loads of National Lakeshore, nearby Sleeping Bear Dunes and plenty of state parks and National Forest provide plenty of outdoor adventures. After all that exercise stop into any of 13+ local breweries and raise a pint, you won’t be disappointed! To see more on this town, click the links below:

Basking in Sunshine and Wine, A Traverse City Guide

It even surprises me when I say Alabama is one of our favorite places! I guess Gulf Shores, Alabama makes the list because this area came out of left field for us, we never expected the coast of AL to be so much fun! 32 miles of unobstructed soft sand and clear water lured us to the beach daily to soak up the sun. We visited in late winter and stayed at the Gulf State Park that felt more like a fancy private park. With a population around 10,000 it’s not a very large town but the surrounding areas including Orange Beach, Dauphin Island, Mobile, Fairhope and Foley provide ample exploration opportunities.

Our Bests: Royal Red Shrimp are simply divine and Doc’s does them up right. To see more on this town, click the links below:

The nickname “City of Subdued Excitement” pretty much sums up our feelings on Bellingham, Washington: they’re not boastful, they’re just quietly awesome! We did zero research on this small town before arriving, but one visit to the local farmers market and we were hooked! Then we popped into a local brunch spot and we were hooked again. A hike at Watcom Falls, a walk through historic downtown Fairhaven, a visit to WWU and a killer cup o’ joe on the waterfront Boulevard Park at sunset and it was hook-line-and-sinker. Easy access to the San Juan Islands, the Cascade Mountain Range and a short drive to Seattle or Vancouver make this town of 80,000 people feel like the perfect spot to settle down between the big cities.

Our Bests: Crab Benedict atop a Belgian Waffle at Mount Bakery Café…need I say more?!? To see more on this town, click the links below:

Bellingham, WA – The City of Subdued Excitement

Surrounded by the Rocky Mountains yet only a short drive from Denver, Breckenridge, Colorado is a town of nearly 5,000 people and is a world class destination for outdoor adventure. If you get bored exploring the 5 peaks and 187+ trails of the Breckenridge Resort there are a handful of other great mountains within a short drive. There’s a top notch distillery, a nationally recognized brewery and a picturesque main street to round out this little towns charm. Sure it’s a little cold in the winter but the summer is absolutely perfect and the mountain provides endless activities all year.

Our Bests: Breckenridge + Dude Sweet Chocolate “Break-Up Potion” and cheap happy hours all over town! To see more on this town, click the links below:

If you haven’t physically been to Sebastopol, California you’ve most likely had a taste of it: famous for Christmas Trees, beautiful wines (especially Pinot Noir, our personal favorite), Kozlowski Farms Jam, GUAYAKI YERBA MATE, Plums, Apples and ACE Cider. With a population around 7,000 it’s amazing how much this little town provides for the surrounding areas of California and beyond. With an amazing local food scene, 15 (or so) local wineries and a quaint little main street make this small town feel much larger than it is. A short drive to the coast for whale watching, a quick visit to that creepy church in Bodega (Thanks Hitchcock, I still get creeped out by crows) and an afternoon in nearby Healdsburg pretty much sealed the deal for us falling in love with this area.

Our Bests: Moustache Bakery in Healdsburg makes the best cupcakes we’ve ever eaten and Iron Horse makes a tasty sparkling wine with (of course) Pinot Noir grapes. Just down the road in Petaluma is home to Strauss – THE BEST (store bought) ICE CREAM IN THE WORLD! To see more on this town, click the links below:

Unusual and Tasty finds in Sonoma County

Hip doesn’t even start to describe the awesomeness that is Santa Cruz, California. With around 63,000 people it’s in our population sweet spot, and even better SC sits just south of the crazy fog you get in San Francisco so the weather is often “Perfect”. Hop on the bike path and ride along the coast to people watch at the boardwalk, pick up some local, organic and tasty grub downtown, swing by the surf museum and lighthouse and finish the day watching the sunset on the dog friendly Lighthouse Field State Beach. Spend the next day high in the redwoods on a hiking trail or browsing the local farmers market. Culture, Nature, Beautiful Weather, Great food and drink…what more can you ask for in a town?

Our Bests: Crazy good coffee at Verve Coffee Roasters and the yummiest ice cream ever at Penny Ice Creamery. To see more on this town, click the links below:

Santa Cruz is Uber Hip Cali

Keep in mind we haven’t been everywhere (yet) so I’m sure we’ve missed several great places along the way. If you want to chime in with a few of your favorites, and why you like them, we’d love to hear from you too. We are evolving as travelers every day, and each new community we visit opens our eyes to another way of life, so if we didn’t mention your favorite spot this time just remember there’s always next year, and the year after……