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The Pickle Barrel - one of Bozeman’s most popular restaurants - remains a community staple, even after 40 years of operation. The squat brown building is barely tall enough for the wooden screen door; the door’s handle is worn smooth from years of hands. Started by Ken and Kerry Olson in 1974, and currently owned by Jenny O’Brien, this is the original Pickle Barrel establishment. Despite Bozeman being one of the fastest growing cities in the U.S., The Pickle Barrel has retained its unique character and remains true to its roots - one of the many reasons this place is so special.
The small space is crowded with a bench cut from half a log, a drinks cooler, a soda machine, shelves overflowing with shirts and sweatshirts for sale, a bulletin board tacked full of local announcements, and a waist-high barrel in the corner. Though the barrel may seem out of place, don’t be fooled - this is a critical part of the establishment decor. Open the lid and floating pickles greet you. For every half sandwich you buy, you get to fish out a free pickle. Put a pickle barrel in the corner and well, now you understand the famous name. The place feels homey — a place where it’s natural for the guy behind the counter to joke with you while he operates the huge grill, which takes up an entire wall. The employees are mostly college-aged and they work back-to-back, as their hands flash over lettuce and tomatoes, quick banter flowing.
The whole sandwiches are enormous, and those sandwiches are what make Pickle Barrel stick out from the rest of the competition. Across Montana, there are other Pickle Barrel locations, but the original on West College is the real deal. These colossal sandwiches are so popular, people who graduated from Montana State University years ago still come back to get their favorite sandwich - making their Bozeman visit complete and sharing the unique experience with family and friends.
Jessica Lewis: How was Pickle Barrel conceptualized? How did this place come about?
Jenny O’Brien: It was already a sandwich shop and the majority of the sandwiches were already in place. Ken and Kerry Olson bought the business in 1974 and between Ken’s marketing power and Kerry’s work ethic, it blossomed into what it is today. They saw something in what the original owners started; it was open for around a year before they bought it. Ken and Kerry are known as the original founders. Between the marketing and getting it out to MSU and Bozeman, Ken had a knack for spreading the word.
JL: Tell me a little about yourself. What made you want to get into the restaurant business?
JO: It was one of those things where I played restaurant as a child, and I look back at that and kind of laugh at remembering that and where I am at now. I moved to Bozeman in 2000, and I was like any young person living here; I had graduated but I hadn’t really figured out what it was that I really wanted to do. Another mountain town seemed great along with the atmosphere and activities and I needed another job. I was amazed and I just fit in, it was such a family oriented, relaxed, chill and fun atmosphere for kids in their 20s and early 30s. I blended in and I just kind of fell in love with the place. I didn’t have too much restaurant experience prior to this, besides some other managerial things, but I picked it up. It was more a mom-and-pop oriented business rather than a restaurant, and that’s what I loved. I saw Ken and Kerry every day, we all did, and it was more like home to all of us. Especially when you’re away from home and away from your family at school, you could have the owners’ presence and talk to them. They got to know all of us on a different level than just as their employees.
JL: Bozeman continues to grow and change; how have you been able to keep the tradition alive?
JO: It’s definitely a respect for what Ken and Kerry built. I would never want to change that. They both said “why fix it if it’s not broken?” They built the cheesesteak, the size of the sandwiches, the cozy atmosphere, and the college vibe. That just fits into this town so well, why would you ever want to change it? What they had a knack for doing, which I hope I’m continuing, is not changing the core of what Pickle Barrel is, but they were able to adapt to the changing times. I remember when they first started taking credit cards; that was a huge thing. They didn’t want to, but they had to. Then they moved into online ordering and that was a big deal! It was something they had to do to compete with businesses coming in. The biggest thing I’ve done, since I’ve taken over, is getting a touch screen register. That is something I never thought I’d do. I was used to the punch-in-numbers register and doing math in your head and your done. That’s not the age we live in anymore, between the phones and everything it’s all touch screen. This is my employees’ lives now, and maybe not mine, but I had to adapt and work with it. It was those types of things where I think it’s more of an adaptation, not a change.
JL: What makes Pickle Barrel unique in Bozeman? What do you offer that other places don’t?
JO: It’s the size of the sandwich. Any time anybody comes in we go through our spiel and ask have you been here before? When we bring down that loaf off the shelf, every single time someone is like “Wow! Oh my god! I can’t eat that!” So, we definitely can’t change the size of the sandwich. You can’t go wrong with the Cheesesteak, a lot of places have their hot sandwiches but Ken and Kerry would have people from all over the world that just crave that cheesesteak; it’s kind of nuts. We get people who come back to Bozeman and Pickle Barrel is their first stop. It’s kind of cool that we have that craving that people want.
JL: What do you want people to experience here when they step through your doors?
JO: Fun, welcoming, and comfortable. They walk in and every single time are greeted with a “hey, how are you?” Or, a “what’s up?” I think that it’s that the shop is so small and so you have to address somebody and it can’t be avoided. I want them to see how much we all get along and how cool it is. You walk in and its kind of like walking into your home where you are going to have an awesome and huge meal. It’s about the whole experience.
JL: What do you enjoy most about being part of Bozeman?
JO: I love the youthful vibe that the college has, of course that’s where I get most of my employees, and just the beauty of it. Sometimes I’m working so much that I walk out at home, and I can’t believe I live here. I love the small town atmosphere it has, even though it’s growing, and I love the businesses that grew up with Bozeman and that are still here. I hope it never changes; that’s what Bozeman is and I hope they never leave. I love everything that’s coming in, but you want those base businesses because that’s why people come back to Bozeman. It’s because of what these businesses built and business owners contributed to the campus, the Museum of the Rockies, the park system and everything that makes Bozeman.
JL: What’s your most popular sandwich?
JO: The Cheesesteak Sandwich. The Bobcat Sandwich is the second most popular.
JL: Are there any upcoming events or specials you want people to know about?
JO: Yes, from June 1st- September 30th, 10% of our sales of the Bobcat Sandwich goes to the Museum of the Rockies for the entire summer.
The original shop is located in an old barbershop at 809 West College across from Montana State University. Attached to the barbershop building is an old house that was renovated in the mid-80s and now serves Wilcoxson’s ice cream, soups and desserts, and provides seating. Pickle Barrel is open daily from 10 a.m. - 10 p.m. and delivery is available daily from 10 a.m. - 9 p.m.
Pickle Barrel is currently found in 6 different communities from Belgrade to Sioux Falls. However, all share the quality sandwiches and community involvement that has made Pickle Barrel so famous both inside and outside of Montana. Pickle Barrel has been voted Best Sandwich in Bozeman for seven years running and continues to draw new fans from distant and local communities alike. Whether you are a regular or someone just passing through, one visit and you will know that Pickle Barrel is so much more than just a sandwich.