Top 5 Most Charming Small Towns

Are you in, or visiting Washington State? Lucky you! Washington is blessed with charming towns. I had to visit a lot to come up with this shortlist of my Top 5 Most Charming Small Towns in Washington.

What’s even better, is that these towns are all do-able as a day trip from Seattle. So if you’re visiting Seattle, and want to get out and experience more, these are perfect for you. Just as perfect, if you’re a Seattlelite, and need to see more of your own State. C’mon – you live in a beautiful state – stop the excuses and get out and explore.

If you’re wanting to experience the best of Washington, a hike would always be up there on that list. However, if you’d prefer something a little less energetic, any of these top 5 most charming small towns in Washington will make a perfect destination for you.

My heart goes into little palpitations when I find a town where character abounds.  Where the owner of the shop is in the shop, sharing her heart and soul in the displays and products around her.  Where the man pouring the drink, knows its full story, because he’s part of that story. 

When traveling through Washington with hubby, it makes life much simpler, if we can find a town to keep us both ably occupied – me delighting in the shops, and hubby enjoying a nice cold IPA somewhere.  This is my secret to a happy marriage. 😉

So, if you’d like to spend a day out of Seattle, sipping and shopping, here’s my pick for your top 5 most charming small town destinations.

1. Downtown Bainbridge Island (Winslow Way)

You will need to jump on a ferry to get to this town, but that just enhances its charm.    Once you get off the ferry, head straight up the road, and turn left onto Winslow Way.  This is the main shopping centre of the island – plan to spend some time here!  If you enjoy shopping, this township will delight you with bespoke boutiques and homeware stores.  If you’ve got hubby with you, and he’s not keen on the shopping (are there any that are?) then you can park him in a brewery or winery where he’ll be happily occupied.

Bainbridge Island - one of the top 5 Most Charming Small Towns in Washington

Distance from Seattle: 30 minutes by ferry from downtown

Top Tip: If you’re only going to enjoy Bainbridge town, leave your car at home, especially on weekends. The ferry lines to return home via vehicle in the afternoons can be extremely long. Here’s all the info you need on the ferry, for passenger and vehicles.


2. Winthrop

Step back into old world charm in the old west town of Winthrop (or ride up on your horse!).    Located along Highway 20 (North Cascades Scenic Biway), you’ll need your camera out from the minute you hit the highway, until you reach the town.   This is a stunning drive, and the town is a fitting destination. 

Winthrop - one of the top 5 most charming small towns


Saunter through town on old wooden boardwalks, stopping to browse at local shops that display products from local craftsmen.    Watch the resident glass blower transform clear melted glass into a colorful art piece.  Sit down and reflect on old western ways over a delicious coffee, or local brew, or grab a sandwich and take it down to the river to enjoy with the view. There is something for all to enjoy in Winthrop. 

Distance from Seattle: 189 miles

Tip: This trip is best done in summer.  Hwy 20 closes for winter.  You can still get to Winthrop, but it’s a much longer way around.   When you do get there, enjoy a cuppa at Rocking Horse bakery, and lunch at Oliver’s. If you’ve got a beer drinker with you, park him at the Old Schoolhouse Brewery (great place for dinner also).


3.   Leavenworth

Visiting Leavenworth is like leaving the States, because the entire town is modeled on a Bavarian village.  It’s success in this is aided by its setting – it sits in the heart of the Cascade Mountains, and the town borders a beautiful river.  

The town itself is filled with artisan shops, eateries, ice creameries, pubs etc – there’s no shortage of retail therapy available to you.  And if you’re a ‘Christmasaholic’ there’s a Christmas shop (Kris Kingl) that will make your heart sing and most likely occupy you for the day. 

Leavenworth - one of the top 5 most charming small towns

BUT – for me – the best part of Leavenworth is actually getting there.  The drive along Highway 2 is simply stunning.  You follow a river for most of the way, with vistas across the river, up to snow peaked mountains.    I had a friend who recently drove from the East to West coast, via several national parks – even after all of that driving, she still said the drive to Leavenworth was a highlight.  

Distance from Seattle: 118 miles

Tip: There are two routes you could take from Seattle – take Hwy 2 for the best scenery!  BUT check the road conditions before you go if you’re traveling in winter.  Leavenworth in winter is another entirely magical experience.


4. La Connor

There are several reasons that may drive you to La Connor.  Most famous would be the beauty of the tulips in the surrounding Skagit Valley fields in spring.  However this cute little town that sits on the edge of the Salish sea, halfway between Seattle and Vancouver, has much to make it a great destination for a day trip.  The town centre is a nationally recognised historic district – this heritage is evident as you wander the township, and brings its character alive.  The area attracts artists, and their art is on display in the many galleries and museums in town.  Feeling pekish – there are fine dining options, alongside breweries and local cafes. 

La Connor - one of the Top 5 Most Charming Small Towns in Washington

Distance from Seattle: 67 miles

Tip: For a special lunch, try the La Connor Seafood & Prime Rib House.

And – if you’re in La Connor, and have some extra time, head north to  Deception Pass – it’s another beautiful area to explore.


5. Snohomish

This is an easy day trip from downtown Seattle, and will appeal to those who just like to wander shops as far away from a mall as possible.  There is a wealth of boutiques and homeware shops, with not a chain shop to be seen.  The town abounds with character, but it’s the shopping that brought me back!   Make sure you have ‘room’ on your credit card!  When you’ve worked up an appetite shopping, there’s a great bakery with lots of lunch options, or plenty of other eateries in town. 

Distance from Seattle: 30 miles

Tip: If you really want to work up an appetite, take your bikes – Snohomish is the start/end of the Centennial Trail, which is built on the old Burlington-Northern railroad line.   Do you know what that means?  It means it’s pretty much flat! 


I truly hope this list inspires you to get out and see more of Washington. It has a bounty of beautiful places to visit – they’re just waiting for you.    

Do you know of any other most charming small towns in Washington that you think should be on the list?  Let me know what you’d include.

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If you’ve read this post, I’m figuring you’re either in Seattle, or will be visiting some time soon. If that’s the case, you may also find this post The Top 10 Things to do in Seattle When It Rains very helpful!

And if you’re looking for more charming towns, consider Friday Harbor on San Juan Island.

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  1. Well now I HAVE to visit Washington and want to go to each of these towns!! The charm calls me! I guess I need to add vacation to my ever growing list!

  2. That town looks so neat, like right out of a movie. Love the look of the buildings and neat stores.

  3. We keep talking about heading south when we visit my parents in Victoria, BC. I think we may just have to go next year!

  4. Leavneworth is my dream town, especially in winter, but I never new about the others. Thank you for pointers!

    1. You’re most welcome. They are all worth visiting – and Winthrop and Leavenworth both offer beautiful journeys as well as a beautiful destination.

  5. This is such an informative blog with so many cute places! I love the photos!

  6. I used to go to Bainbridge Island with my grandmother when I was a child…great memories!

  7. Leavenworth looks like a dream! I miss Germany so much. Would love to visit Washington and see these gorgeous places!

  8. I haven’t been to Washington yet, but it’s on my list for 2021. Thank you for your informative post about these cute towns, great reference here!

  9. Such a beautiful blog on Washington.I have not been to Washington but I know it’s a beautiful place. Loved the Bavarian architecture!

  10. I am fascinated by the faux-bavarian villages all around the US, so I’m glad I now know about Leavenworth. Have you been to Helen in Georgia? It’s got the same look and feel! Washington is on my list of places to visit, so I look forward to all these!

  11. This post makes my Washington heart so happy! I’ve been everywhere but Winthrop. Hope to get there this summer!

  12. I can see why these made the Top 5 Most Charming Small Towns in Washington! They are so charming! And love they are just a day trip from

  13. Emma | The Checklist Chic says:

    These towns are all so cute! Almost like they came out of a movie! Adding to my bucket list.

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