When I moved to Bozeman 31 years ago, I lived less than half a mile from the Pickle Barrel for my first year at MSU. My palate was as naive as I was, my wallet was thin, and I didn’t explore the Bozeman food scene much.
      
The Pickle Barrel was already an institution in Bozeman when I arrived, having served our community delicious, huge sandwiches for over two decades at that point. Opened in 1973 and taken over by Ken and Carrie Olsen in 1974, The Pickle Barrel is Bozeman’s original sandwich shop. This is their 52nd year on College Street, and there aren’t many places in Bozeman with the nostalgia, ambiance—and definitely not the taste—that you’ll find there. 

For the past 24 years, Jenny O’Brien has been leading the team at The Pickle Barrel, holding its traditions strong, and keeping the vibe old school. She carved out a few minutes to speak on the phone as MSU students flooded campus for a new school year, and the energy on College Street was ramping up for another season of sandwich slaying.

Angie Ripple: What do you hope people will experience when they walk through your door?

Jenny O’Brien: A guy just asked me this last week. I think, first and foremost, just fun. I want them to feel like they’re part of something. I want them to have fun. People walk in, and I think they’re not surprised, but you walk into a chain [restaurant] and it seems very... sterile, I guess is the word. But you walk in here, and you can tell this shop has been around for ages. It’s almost like walking into a museum because we have pictures on the walls from the ‘70s, ‘80s and ‘90s. We have pictures up there from a month ago. You can see the fun that has been had by the owners and the employees. I think it’s just a different feel, and sometimes it is almost hard to describe. But I guess a feeling of belonging, too, because when you walk in the door, we’re very genuine in our ‘Hey, how you doing? What’s up?’ My crew is happy to be here; they’re happy the customers are there, and they’re in a good mood.

I definitely have had people come in—depending on how much research they did, they obviously have been told to go to Pickle Barrel—and they walk in and they’re like, ‘Wait a second. Where do we sit?’ We’ve even had people call and ask for reservations, which makes us all kind of laugh. We’ve added about 10 seats where we used to serve Wilcoxson’s Ice Cream, and where we currently do all our baking. We also have outdoor seating, which is great for families in the summer, and picnic tables on campus.

AR: What would you say makes The Pickle Barrel unique in the Bozeman food scene?

JO: I would say its longevity, its location near the MSU campus, and the sort of family atmosphere. Ken and Carrie definitely always created a family atmosphere. They did a lot of outings together, parties and skiing. It was more than just a job.

I think it definitely has that mom-and-pop hometown feel to it, especially when you walk into the shop. It’s a vibe, which is how I’ve described it many times.

AR: What menu item do regulars keep coming back for?

JO: The cheesesteak. It’s the most popular sandwich on the menu. It’s grilled steak, onions, jack cheese, and a secret recipe barbecue sauce.

AR: Is there a second favorite?

JO: The Bobcat. That is roast beef, turkey, Swiss cheese and jack cheese. All of these are on our own bread that we bake fresh every day.

AR: Do you have a favorite?

JO: Yes. Mine is the pepper steak. That is grilled steak, onions, green peppers, and cheese. I would say that one is a staff favorite as well.

AR: What do you personally enjoy most about being part of the Bozeman community?

JO: The energy of it, especially with the college. The students bring in a different level of energy.
I started as a college kid, and I work with college kids. They are a lot of fun, and I would say they keep me young. They kept Ken and Carrie young. But I would say just the energy of Bozeman, the community, and the support they give to Pickle Barrel. I can’t tell you how many times I’ve heard, ‘Pickle Barrel is an institution. My parents brought me here as a kid.’ It definitely is a strong part of what Bozeman is.

AR: What do regulars know about The Pickle Barrel that first-time visitors might not?

JO: Well, unfortunately, we had to move the pickle barrel. You used to be able to walk into the shop and grab your own pickle, preferably with tongs. That’s what a regular will know. After COVID, we had to move it behind the counter. It took us a while to get used to asking people if they wanted a pickle because usually you would just grab your own.

AR: Is there something that your regular diners are surprisingly picky about?

JO: Once again, we used to get a whole pickle from Heinz forever and ever. After COVID, Heinz just stopped making pickles, and it took me forever to find something comparable as far as the taste, the visual and the size. The closest thing I found is a pickle that is cut in half. And they do not like that. I’ve got people who refuse the pickle because it’s half. I try to tell them exactly what I just told you, but we kind of chuckle because it’s free. You’re not paying for this. And it’s really out of my control. I would love to have the Heinz pickle back, and I can’t believe they just stopped. If we were to measure the new one, and weigh it, it’s the same as the other pickle. It’s just the visual of, ‘Oh my God, they cut it in half.’ So it is kind of funny, but there’s really nothing I can do. On the flip side, we still get a lot of compliments on it. It’s a great pickle. It’s the best thing I could find. And my gosh, if Heinz ever decides to make pickles again, I will definitely bring that back.

AR: Has your menu changed lately? When was the last time something new was added?

JO: Over the 24 years that I have been with the shop, the only two additions were our Downtown Chicken and the Blue Streak, which is probably the newest sandwich. The Blue Streak is basically grilled steak with blue cheese dressing, mushrooms, lettuce and tomato.

As far as if you were to ask me to predict any future sandwiches, honestly, I would say no, just because I feel the menu is kind of as good as it can get. 

Although, I will say there is an opportunity for a possible Pickle Barrel secret sandwich menu.

AR: Is there anything special happening in September that doesn’t happen any other time of the year?

JO: Something that has been happening over the years is that gluten-free is becoming a bigger request. Although we will never get a gluten-free bread, we have something seasonal that will move into September. It’s more of a midsummer-to-fall offer, and it’s our pickle pocket. Basically, it is a huge cucumber that we pickle in-house and season. They’re about the size of our half sandwich, so they’re big. We carve out the middle, and then you put whatever sandwich you want in it. It is very popular in the summer, and that’s also the best time for me to get these cucumbers. We’ve advertised it is, ‘No bread, no problem. Try our pickle pocket.’ If you’re gluten-free and you don’t really like pickles, we also offer any sandwich as a salad.

AR: Is there anything we missed that you would like readers to know about?

JO: I’m so grateful for the shop being as old as it is, and for the new types of restaurants moving into Bozeman. They’re very high-end, I guess I would say. We don’t really fit in with them much, which is maybe why we’re still super busy. We’re definitely different. I am so thankful for the many years and the hard work that Ken and Carrie put into it so that I could just maintain what they built.

AR: Are you guys still doing your own deliveries?

JO: We do, yes and no. We deliver our catering orders, but I did make the decision to go with DoorDash because DoorDash has the ability to go everywhere, and it just wasn’t financially feasible for me to do that. You can order on our site, and DoorDash will deliver.

Whether it’s been two weeks or twenty years since you’ve visited The Pickle Barrel, it really hasn’t changed a bit. It still offers the same thing it always has: a great sandwich, a friendly welcome, and the feeling that you’ve walked into something that belongs to Bozeman.