best outdoor activites in bend oregon

Our Held at Gunpoint Top Ten Best Towns

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.

top 10 towns

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:


best small towns

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:


top ten towns north america

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:


best towns to live

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:


best small towns

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:


top ten towns to live

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:


best small towns to live

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:


top ten towns

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:


top ten best towns

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:


top ten best towns

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:


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……

Famous for my "how-not-to" videos, and typically the man behind the camera, sometimes I’m forced to be here in the “spotlight”. When you see my face you’re probably reading something more technical than adventurous, but either way I do my best to tell it like it is and infuse my opinions into the commentary…after all this is a blog and not MSN.

Comments (34)

  • Many of these are on my favorite towns list too! I’m especially excited to see Traverse City on the list because, as a former Michigander, the northern lower peninsula is ridiculously beautiful and amazing. Also, Bellingham is on my short-list of places I’d consider settling. I know you guys enjoyed Alaska, I recommend catching the AK ferry out of Bellingham sometime!

  • Dana S

    I follow you with relish, dreaming about the opportunity to get on the road. I live south of Belllingham, WA and the area of Skagit and Whatcom counties is full of fun things to do. Except for the unremitting rain in Winter, it is a great place to live. I’m in the process of preparing my sticks and bricks to sell and looking at one of the small RVs in your series. Thanks for all the GREAT info and the interesting travelogs. I like your new look!

  • Hey guys! I’m not saying it would make your top 10, but based on this list, you should check out Lawrence, KS one day. Craft beer: check (Free State Brewery); cool downtown with cool stores and delicious food: check (Mass Street); cultural advantage from being college town: check; not too small but not too big: check (around 100,000).

    Late spring/early summer is truly lovely.
    Disclaimer: please ignore state politics. They’re preposterous.

    • Thanks for the suggestion! We haven’t been to Lawrence but we hear such great things about it. We are going to have to make sure we check it out next time we are that direction.

  • So good to learn about those cities. I am looking to relocate my base outside of California before traveling. Washington, Nevada and Texas have no state taxes so my retirement would go further for fuel costs. I hear Mississippi has no taxes on IRA’s and 401K’s. I kind of like Bend as Oregon has no sales tax which is probably why RV sales are popular there but I think you have to establish residency for a year before getting DMV to give you Oregon tags. But real estate tax is high in Oregon. What are real estate taxes like in Texas? MHSRV looks like a great place to buy. What are sales taxes in Texas?
    You have given me some more places to put on my list to visit. -Thanks, Clay

  • Cathy

    Sedona, AZ is a must stay and see place-like no other.

  • Been to many on this list…I’d have to say Bend or Santa Cruz might be tops on this list. Several I’d like to check out, like Gulf Shores…AL is one of only 3 states I’ve not yet been to.

    • Hey Mike! I am surprised you haven’t been to Alabama yet, you will love it! We are headed that way here in another week or so…you could always come camping with us!

      • Yeah, me too…I was really close a few months ago as I spent 10 days in Louisiana, but just hasn’t happened yet. Soon, I hope.

        Safe travels!

  • Rob Lee

    Not sure if you’ve ever been, but next time you are in the Asheville area, I suggest taking a drive down to Greenville SC (about an hour south).

    It’s a great little city with a beautiful downtown, and probably where we’ll return to if we ever decide to leave the road.

    • We have not been to Greenville but we hear great things about it! We will definitely add it to our list!

  • Ben Ferguson

    Funny you mentioned Mustache Bakery. We ate lunch at Pizzando in Healdsburg a week ago and when we didn’t have their dessert, the waiter recommended Mustache down the street. We had their Salted Caramel cupcake. My wife had been looking for a good filled cupcake and they sure filled the bill!

      • Ben Ferguson

        Hah! Now I know how to torture you!

        Seriously, thanks for your top ten. Several we’ve been to and look forward to others. I’m sorry we missed Sebastopol on our drive through Sonoma. We stayed in Napa for Thanksgiving and had a great (but expensive) time.

        • Yes, sadly that is the one downside to Napa, so easy to spend money there!

  • Too funny that Bellingham is on this list as that is where I grew up. I haven’t been back for a couple of decades (half my life) so I don’t have a crystal clear memory of the town, but I still find it amusing that it is on your list. I do need to go back and refresh my memory, but there are sooooooo many other towns to visit first… 🙂

  • Jim & Warrene Paddock

    Looks like you are back in Dallas for a while. It will be good to be with family and friends for the next few weeks. My wife has been to Bend to visit her family. So we are glad to see that is made your list. She absolutely loved it and wants us to visit up there when we can. She and her mother took the train from Dallas to Oregon. While it isn’t a camper, she loved the California train portion of the trip. Be safe.

      • Corey

        Just curious about your location in the Dallas area. Your current location map shows you’re off the Campion Trails near Valley Ranch. We lived (and still own a house) just off of the trail on the south side of 635, not even a mile from where you’re at. I used to cycle the trail every week but I didn’t realize you could park there overnight. Did you need a city permit or anything? We just acquired our first RV so I’d be interested to know.

        It’s too bad we don’t still live there; we’d invite y’all over for some of my homebrew since you’re craft beer enthusiasts. 😉 We really enjoy all the posts so keep up the great work!

  • We haven’t been to most of the places you name but we like Charleston, SC. One we like is Murfreesboro, TN. We were recently there for a few days and love the places.
    I like the fact that you have favorites all over the country. We were talking with a FT friend yesterday who said how much they liked Gulf Shores, AL. We have to check it out. And the other places you list where we’ve not been yet.

    • There are so many beautiful and unique places around the world it is impossible to settle on just one. 🙂 We always say that everywhere has something to offer, even if you have to look a little harder to find it. Hope you make it to some of these gems soon!

  • Randy Spencer

    It’s that the point of an RV you can have a little house on all those and many more cities. Now I just need one that drives itself there.

    Exquisit list. Not a loser in the bunch. I have been to all but Gulf Shores, there are others that excite me, but I could never take my lifetime of travel and suss a better list than you have done.

  • Lynda

    Thank you for this list! When we hit the road we will try to visit all of these places. I’m curious to know if you have traveled through Mississippi? If the coast of Alabama surprised you, try going up the Natchez Trace in spring time. GORGEOUS.

    Here’s a dumb question. What is the little green icon on the left side of the page on your website? I can’t figure out what it does.


  • We’re new to RVing but have followed your adventures from the beginning. Can honestly say that we’ve visited all of your Top 10 towns (Traverse City cherry pie!)…about half during last summer’s 12000 mile cross-country trip…the other half during many non-RV travels. New Years Day we depart for a winter get-away to Baja Sur, Mexico. Keep On Truckin’!

    Richard and Gwen
    “Duckin’ Out!”, Leisure Travel, Unity 24TB
    Whidbey Island, WA

    • That’s Fantastic!!! And you are traveling in one of our favorite small RV’s! Hope to see you out there!

  • paul van

    AWESOME, I think I’ll buy a little house or cabin in every town!

  • Martine

    We were deciding to buy between Bellingham and anacortes Washington. We went with Anacortes because only 16,000 people. And we can always visit Bellingham.

    • Anacortes is beautiful and such a great location. I can’t blame you!

  • Jerry Minchey

    I know you said that the list was in no partricular order, but I was happy to see that Asheville, NC was the first town you listed.

    I stay in and around the little town of Black Mountain, NC (15 miles east of Asheville) most of the summer and will be heading to Florida to roam for four months the day after Christmas. Then it’s back to the NC mountains.

    I like your taste in towns to live in.

    • Well Jerry, great minds do think alike 🙂 Hope to see you down in Florida!


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