You’ve been to Subway, right? Imagine Subway on steroids—that is exactly how I would describe The Pickle Barrel, a small business located on College Street with lots of amazing sandwiches, and even some merch! Owned by Jen O’Brien, the menu includes both hot and cold sandwiches, salads, and some baked goods. If you’re more of a turkey and cheese kind of person, they’ve got that, but they also have sandwiches like a hot meatball sub. Pretty much any combination you can think of is going to be on the menu. The best part about The Pickle Barrel is that they offer not only quality food, but quantity as well. At 17.5” long, their sandwiches are HUGE! Fortunately, you can order a full, half, or quarter length.

Maisie Bissell: How was The Pickle Barrel conceptualized?

Jen O’Brien: The Pickle Barrel was founded by Ken and Kerry Olson in 1974. Prior to Ken and Kerry purchasing The Pickle Barrel in 1974, it was an established sandwich shop, but The Pickle Barrel is what it is today because of Ken and Kerry.

Together, they created the fun atmosphere, along with the amazing and huge subs that have become truly an Institution in Bozeman, if not in the entire state of Montana. Ken and Kerry had the ability to bring crews together and create lasting friendships. From their employee ski trips to Grand Targhee, to summer parties riding jet skis, lasting memories were created. To this day, past employees frequently visit the shop and reminisce about their time at The Pickle Barrel.

MB: What do you want people to experience when they walk through your doors?

JO: When people walk through the door, I want them to be reminded of their college days! We have a lot of MSU Alumni, and as soon as they walk in the door, I can see the memories come flooding back. For those that did not attend MSU, I want them to experience a crew that acts like they’ve been working together forever. A super fun, chill atmosphere, where the music is playing, the crew laughing and putting out sandwiches at a record pace, like a well-oiled machine. Sometimes it’s as if you are walking into a party. Quite often the crew describes the job as a place they come hang out with their friends, listen to music, and make sandwiches. They laugh and add, ‘we get paid to do this!’

MB: What makes The Pickle Barrel unique in the Bozeman Food Scene?

JO: Pickle Barrel is unique because of the size of our sandwiches. When a new customer asks about the sizes and we show them our whole-size sandwich, every single time, eyes widen, and jaws drop. I also think Pickle Barrel is one-of-a-kind because it has not changed whatsoever since 1974. In fact, there are jars of pickles from the 70’s on the shelves, the original chalkboard menu board, and old-time photos from some of the very first PB crews.

MB: What do your regulars keep coming back for?

JO: Hands down, the regulars keep coming back for our famous cheesesteak! It’s grilled steak, onions, Jack cheese, our own signature BBQ sauce—and you can’t forget the pickle. Every sandwich gets a pickle from the actual barrel.

MB: What is your personal favorite menu item?

JO: My personal favorite menu item is the Pepper Steak. Grilled steak, onions, green peppers, and Jack cheese! Not that it needs anything else, but a little chipotle sauce gives it an extra kick!

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

JO: As a local business owner, the loyalty of the Bozeman community means the most to me. With the growth of Bozeman and the numerous eating establishments opening, I am incredibly grateful for the Bozeman community and their support of Pickle Barrel. I can always tell a Montana native because the ‘I remember when’ story always includes coming to Pickle Barrel as a child and grabbing their pickle from the barrel! To see these same people bringing their children to Pickle Barrel makes me so thankful for the Bozeman community.

MB: Do you have anything coming up that readers should know about?

JO: I know that Pickle Barrel’s reputation reaches across Montana. With only a few locations, not many customers can get their favorite subs on a regular basis. This may change! We are working diligently on providing an online site where customers can place an order to be shipped anywhere in Montana. Along with this, Pickle Barrel will turn 50 in 2024! There are plans for a Pickle Barrel reunion; this won’t be any regular reunion, as the stories stretch over 50 years, with hundreds of employees. We’re planning a week-long celebration.

MB: How often do you change your menu?

JO: The Pickle Barrel menu has remained the same since 1974. In fact, the menu has never changed, it has only had a few additions. ‘The Pickle Barrel way’ is to stick with what works; keep it simple, so that you can provide the best, most consistent sandwich for our customers. Over the past 45+ years, the original menu has remained the same, only four sandwiches have been added.

MB: Do you have any goals for expanding The Pickle Barrel?

JO: Currently, there are no plans for expansion. Billings, Livingston, and Sioux Falls, SD have a Pickle Barrel. In the past, there have been Pickle Barrels in Great Falls, Missoula, and Belgrade.

MB: What qualities do you look for when hiring new employees?

JO: The quality I look for most in a potential employee is the ability to hold a conversation with me. The shop is extremely small; there are no hiding places, no cubicles, or divisions within the kitchen. A person needs to be able to converse with their co-workers. In turn, this will allow for everyone to get to know each other, and the result is a more efficient workplace. Employees who know each other get along together, and therefore work better together.

If it’s been a while since you’ve been to The Pickle Barrel, I suggest you go for a delicious meal and a genuine Bozeman experience. Since opening in 1974 it has basically stayed the same! Try the Big Sky Special sandwich, my personal favorite. The Pickle Barrel is a perfect place to go out to lunch with some friends, especially if you are a college student living on campus. They also offer delivery, so you can be anywhere in town to enjoy a mega-sandwich. Hours are 10 am – 10 pm Monday through Saturday, and 10 am – 5 pm Sundays. Visit picklebarrelbozeman.com to check out the menu.