Entry No. 33 — the Bozeman file — filed under: speakeasy
Devil's Toboggan
Up an unmarked stairway on the second floor of a converted factory in the Cannery District, Devil's Toboggan hides a velvet-and-crystal cocktail den that's been one of Bozeman's worst-kept secrets since 2018. The drinks lean hard into the golden age of the 1920s, with classic bourbon-forward cocktails alongside an eclectic menu of tapas-sized small plates. Plush red seating, chandeliers, and lantern-lit entryways make it feel a world away from the brewery-and-restaurant complex below.
The story
Up on the second floor of a converted pea cannery on East Oak Street, you walk past industrial drywall and stairwells into a room that feels engineered to hide you away. Owner Chris Burgard opened Devil's Toboggan in 2018, tucking a velvet-and-crystal drinking den behind an unmarked door above the ground-floor commercial spaces. There is no flashing sign on the street; you either know suite 2B exists or you walk right past the stairwell.
Once you pass the lantern-lit entryway, the concrete factory hall gives way to dark plush red booths, heavy chandeliers, and a bar focused on golden-age drink construction. The bartenders pour spirit-forward cocktails heavily weighted toward bourbon and pre-Prohibition recipes, paired with an eclectic kitchen menu of international tapas plates. Before you even open the drink menu, the house greets seated guests with a tiny complimentary welcome pour.
Burgard eventually expanded on the building's hidden-lounge setup by opening a late-1960s lounge, It Will Always Be That Way, just a few doors down the same hallway. While that sister venue leans into vintage TV trays and orange laminate decor, Devil's Toboggan remains the darker, quieter anchor built for slow sipping away from the brewery noise downstairs.
What it's like
Finding Devil's Toboggan means taking the stairs up to the second floor of 113 East Oak Street and scanning the hallway for suite 2B's plain, unmarked door. Inside, the vibe shifts immediately from utility hallway to dimly lit 1920s lounge lined with velvet booths. Table space is tight and drinks are crafted carefully, making it a heavily booked date night spot on weekends. To avoid a wait, book a reservation ahead of time or arrive right around the 4:00 PM opening on a weeknight, take your seat, and sip the complimentary welcome splash while you read the cocktail list.
The move: Find the unmarked upstairs door, settle into a velvet booth, and split a tasting flight of 1920s-inspired cocktails with a few small plates.
- 📍 Bozeman
- 💸 $$
- ⚡ Up for anything
- 🌗 Indoors
Where: 113 E Oak St #2B, Bozeman, MT 59715
Hours: Added 2026-06-24 — confirm current hours before you go.
Pair it with
- It Will Always Be That Way — Owner Chris Burgard created both venues in the same building, making it seamless to step out of 1920s velvet and walk down the hall into a late-1960s retro parlor.
- Tinworks Art — Spend the late afternoon walking through large-scale art installations in raw industrial spaces nearby before settling into a quiet booth in the Cannery District.
- Studio Wheelhouse — Take a hands-on workshop two blocks away before heading upstairs for a post-craft cocktail.
- est.1864 Noir Bar & Restaurant — Compare two distinct historical drinking moods by pairing an upstairs 1920s lounge with a basement bar modeled on an 1860s Main Street saloon.
Good to know
How do I find the entrance?
Head into 113 East Oak Street in the Cannery District, go up to the second floor, and look for suite 2B. The door has no prominent bar signage.
Do I need a reservation?
Reservations are strongly recommended, particularly on Friday and Saturday evenings when the limited plush booths fill up fast.
What kind of food and drinks do they offer?
The bar serves 1920s-style classic cocktails with a focus on bourbon, along with wine, craft beer, and a menu of international tapas-style small plates and desserts.
Do they really give you a free sample drink when you sit down?
Yes, guests are greeted at their table with a tiny complimentary welcome cocktail pour.
Plan a visit & invite your people →
Further reading: Official site · Yelp · visit-bozeman.com · bozemandailychronicle.com · saltlakemagazine.com · bozemanmagazine.com
last checked: 2026-06-24