Home Pie Making Small Pies Under Montana’s Big Sky

Making Small Pies Under Montana’s Big Sky

Making Small Pies Under Montana’s Big Sky

My Trip to Wonderful

My friend Jean lives in Columbia Falls, Montana, and started “Sunday Market” in her community as way to bring people together, have fun, and inspire folks to create, grow, and sell things and services for added income. Jean gets stuff done! Several mountain ranges and one time zone away, I marveled at Jean’s hard work and hometown dream to make an outdoor market happen, so of course I wanted to go see her and experience the market for myself. The summer flew by and I finally had an opportunity to head over and help her make pies for the final Sunday Market of the season.

montana RV camper
Columbia Falls Four Seasons, 5-Star Accommodations: Home Sweet Home for a few days…just keep an eye out for bears. 😉

Pie-Making Prowess

Jean is THE pie lady of Columbia Falls, a well-deserved and deliciously divine title for a woman who can make your mouth water merely by reciting a recipe or recounting her pie wares. Since I fancy myself as I’m a bit of a pie guy, I wanted to help her bake, see her place, and check out her small town and market in the shadow of Glacier National Park.

Jean, the pie lady of Columbia Falls, Montana giving the people what they want: personal-size peach pies! She calls them Cutie-Pies!

Prying Myself Off the Island

I must confess that leaving my farm and my island is like prying a barnacle off of a pier. For me, travel takes a bit of planning and managing the home-front; first, I need to find a capable and engaged soul to watch the farm, water the orchard and greenhouse, caretake the house, and parcel oodles of hugs, kisses, and butt rubs on my Buddy. Of all those things, loving Buddy is the main event. Fortunately the stars aligned, clouds opened up, and the angels sang. House-sitter and now friend Susan came into my life through a recommendation and was immediately smitten with Buddy and the farm (in that order). Job filled. Buddy spoiled. Tom happy. If I had stayed a few days longer in Montana, I fear Buddy would have traded me in for his kind, caring and fun-loving new pal. (Thank you Susan, Buddy is still raving about you!)

Susan texted me Buddy updates and pics. Here’s a snapshot of the mayor joyriding around the island with his favorite nanny.

Baking My Way to Sunday Market

Jean started Sunday Market in Columbia Falls: spearheading and organizing the weekly summer event by getting permits; finding and organizing vendors; and basically getting the word out and making it happen. When I asked if I could come help her, she said, “of course!” So off I went to join my sister in pies for an intense and wonderful weekend of baking and laughing and sampling.

Blackberry Cutie-Pies! Let the pie-making begin! Note to self, next time bring an apron.

The Journey Begins Long Before the Airport

One of the jokes of living on an island with limited ferry service is that it takes longer to get to the airport than it does to fly to your destination. Flying east from Seattle to Kalispell, Montana takes about an hour and a half. Gaming late ferries, dicey parking options, unrelenting traffic and circuitous security lines usually takes at least four hours from island doorstep to Sea-Tac departure gate. Sometimes you feel like Indiana Jones in sweaty pursuit of a fabled destination–minus the poison darts and rolling boulders.

mini peach pies
I may have to bestow another title on Jean: Queen of Crimping!

Making Pies, Cakes, Cookies and Scones!

We started prepping pastries on Friday, the day I got there, but only after a fine Montana steak at the Night Owl restaurant. Saturday morning started with a frothy cup of espresso and a lumberjack breakfast. Then, I awaited my baking orders. Jean is a model of efficiency and organization, so it was a pleasure to be part of her kitchen operation. And besides, she’s excellent company.

homemade poptarts
Jeans made two types of “pop tarts” for this Sunday Market, one with fruit (strawberry shown above) and another with savory fillings, such as cream cheese, gruyere, scallions and chopped parsley.

In a regular Santa’s workshop, these elves measured, mixed, kneaded, chopped, rolled, crimped, baked, cooled, portioned, and packed up some of the tastiest baked goods in the valley. We rewarded our efforts and full day of baking fun with a tasty Italian dinner in nearby Whitefish–a fancier version of Montana.

The starting lineup: Jean’s cutie-pies. Fillings included: blackberry, apple, strawberry-rhubarb, peach, pecan, cherry, and triple berry.

Big (and Little) Pie Country

On Sunday, a little after 7 a.m., we blocked off 6th Street West, in front of City Hall and the library, and begin to set up the market. So what did we sell at Jean’s booth, Prairie Girl Farms? From local farmers, we offered fresh corn, tomatoes, peppers, cabbages, squash, onions and plums. And on the pastry side, our marathon Saturday bake-a-rama produced Cutie-pies, Montana-shaped sugar cookies, Plum-Almond Cake, Shaker Lemon pie by the slice, Big Mountain peanut-butter cookies, Strawberry jam pop tarts, savory cheese pop tarts, cherry-lemon yogurt cake, and scones. And I’m delighted to say, we sold out of everything. I’ll be featuring some recipes and how-tos in the coming months on the blog, starting out with the pop tarts, which you can make and freeze for later, too.

shaker lemon pie unbaked
Oven-ready Shaker lemon pie!

Jean’s Sweet-on-all-levels Homestead

Jean Flynn is one of the most creative, skilled and energetic people I know. She conjures magic always and has transformed her homestead into a welcoming place of delight and hospitality. During the summer, she rents out her home on VRBO (Vacation Rentals by Owner) and lives in a teeny-tiny house on the property. The half-tent platform (shown below), one of her dreamy spots on the property, beckoned this baker for several quick breaks between bake times.

napping tent montana
Montana Shangri-La: Jean built this dreamy open platform tent for summer reading and napping and wiling away the day between chores.

Amazing Jean

Jean is also an interior designer and maker of amazing textile products like custom window treatments, slipcovers and pillows. Here’s her site: jeanflynninteriors.com. She also makes Jeanie’s Beanies, wonderful beanies (as seen on the dashing chap below) made from cashmere sweaters she finds at thrift shops. But that is just a small thread of the quilt that has been Jean’s life. Here’s a fun article about her that gives you an idea of her creative chops: https://www.sfgate.com/homeandgarden/article/Stage-presence-Jean-Flynn-decorated-her-Seattle-2677246.php#photo-2150355

I am sporting one of Jean’s cool caps, Jeanie Beanies, one way to keep my little bald spot toasty, comfy and styling on a chilly Montana morning.

A Big Sky Thank You to the Hostess With the Mostess

It’s rare that I tear myself away from my island hideout, but my trip to wonderful to see and help Jean was a delicious respite and reconnection. And Jean tells me a pie shop may be in the works, so I’ll keep you posted. No one should be without pie. So thank you Jean for the best time and the most baking fun this man has had in a while! I love your slice of pie heaven, and I reveled at having been a part of the activities that make it and you so special.

cup of joe frothy

My Favorite Welcome-Home Committee of One

I love being missed as much as I love the reunion!
Safe travels my friends wherever the winds and waves take you!


  1. Really fun post, Tom. Thanks for sharing your adventure! Lotsa inspiring travel, cooking, kitchen set-up, community activity, and building ideas nestled throughout like Easter Eggs. We too live on a Puget island and never leave, but you make a good point for venturing out to nurture connections with dear friends.

  2. Very fun recount of your Montana adventure, Tom — glad you’ve found the perfect home/pup sitter and all the stars aligned for you to enjoy everything Columbia Falls was serving up.

  3. I would buy one of Jean’s beautiful pies in a heartbeat! The problem would be choosing.
    I really loved her little hideaway spots on her land where one could just plop down and enjoy a good quiet read and a nap without any interruptions.
    I’m so glad Buddy let you go for a little jaunt on your own. He obviously was perfectly happy with his lady looking after him with the respect due the mayor of his empire.
    If I lived in your idyllic spot in the world I don’t think anything would prise me away – not even Jean’s pies!!
    Thankyou Tom for another enjoyable breakfast read. :))

    • Thank you Mary for the nice note and kind words. Jean is having a pop-up pie shop in October should you find yourself in Columbia Falls this autumn season. 🙂

  4. Thank you so much for taking us in this incredible adventure! You had me at hello with “Pies and Montana Skies”.
    I first met you through the Pie Making class hosted by Margo Tantau and I’m so happy to now be able to read your amazing blog!
    You are a gifted writer and I would love to meet Buddy someday.
    Tell him I’m up for “butt rubs” 🤗

    • Hi Debbie, nice to meet you! Thanks for the kind note and support. I sure had fun hosting the pie-making class with Margo. We’ll have to do another one! Buddy says he can’t wait to meet you. Well wishes! Tom and Buddy

  5. Tom Conway! I have admired and worshiped your foodie goings-on on Vashon for many years and I hope you noticed when you looked into my scribbled recipe book page after page said Tom Conway‘s recipe! What an honor and a joy to have you visit Prairie girl Farms and how lucky to have some one with your chops in the kitchen slinging Buckle batter and pie dough! Next up: a visit to Vashon and then after that I hope you will come on the train and bring Buddy because you know he would be super welcome here. Thanks for taking the time to write about your adventure! Mush mush!! Love soup!

  6. Oh, gosh-what a fun article & story about how to ‘live the life❣️‘ My fav food is pie, so you, Tom, & your pie buddies like Jean, amaze me❣️I found you by listening to Margo, & your laid-back pure heart made the podcast joyful❣️

    • Margot I’m sitting down to my first cup of coffee, and reading your lovely note. Thank you so much, what a generous compliment. I have such fun with Margo and we have the best time together. She’s a busy girl so when I get her to myself (even on a podcast) I’m beaming. Thanks again for making my morning, and here’s to lots of pie in our lives!

  7. Tom, is this your latest post? If so, please fill us in on your latest adventures on the island and what’s up with Buddy

    • Hi Laura, Buddy and I are doing fine. I want to get back to posting on the blog regularly, but I’m sorry I haven’t found my writing mojo as of late. I hope to change that soon. Thanks for thinking of us.

  8. Glad to hear all is well! I wanted to reach out and make sure I hadn’t missed any exciting new posts. I’m sure you’re busy right now with weeding, mowing, etc.
    Take care and I will await your next post😀

  9. Tom,

    Just realized – it has been 18 months since I heard from you and Buddy. I hope all is well on Vashon Island?


    • Hi Tad, thanks for checking in on us. Buddy and I doing well. I just took a little break for the blog, but hope to jump back in soon. Again, thanks for your kind inquiry. cheers, Tom and Buddy


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