At the start of 2026, the stretch of downtown Helena where Sixth Avenue meets North Last Chance Gulch had several empty rooms. Last Chance Market and Catering closed around January. O'Toole's Bar and Lounge was gone. The Original Montana Club had been shut since its 2024 bankruptcy. Benny's Bistro was waiting for a new owner.
All of those rooms are open again this fall. The new tenants didn't pile into the same dinner rush. Each one took a different part of the day. Together they cover a two-block walk from a 10 a.m. sandwich counter to a basement bar that stays open until midnight on weekends.
The Late Morning and Lunch Hours Went First
The quickest turnaround happened at 32 W. 6th Ave. The building's owner was a regular at the Wassweiler Dinner House, and after Last Chance Market and Catering closed, he asked Wassweiler owner Keith Jackson to take the space. Jackson got the request in March. With $5,000 of his own money and some help from the landlord, he opened Jackson's Market and Deli in mid-July.
This is the Wassweiler kitchen working at lunch speed. Jackson's bakes focaccia every day, sells meats by the slice, and keeps a regular menu next to rotating seasonal dishes. The $16 chimichurri steak sandwich with strawberries and feta is on the regular menu. A $7 spicy watermelon gazpacho was one of the summer specials. Local reporting in July gave the hours as Tuesday through Saturday, 10 a.m. to 3 p.m. That's a daytime-only schedule, and it fits a downtown full of state offices. Jackson grew up in Missoula restaurants, where his parents ran Front Street Pasta and Wraps from 2002 to 2012.
A few doors away, Bambino's Deli had its grand opening on Thursday, Sept. 3, in the old O'Toole's space at 330 N. Last Chance Gulch. It served 50 sandwich orders in the first few hours. Owner Derek Kraus coaches Helena American Legion Baseball. He came back to Helena after a career with software startups in Boulder, Colorado. His sandwiches cost $10 to $15 and are named after places in Italy, like the Dolomites and Naples. Customers can choose from six cured meats and three kinds of salami. On opening day, several people asked him what capocollo and bresaola taste like.
"Everyone knows prosciutto; it's like the bacon of cured meats," Kraus told the Independent Record.
Bambino's overlaps with Jackson's at noon but runs much later. Reported hours are 11 a.m. to 4 p.m. Monday and Tuesday, and 11 a.m. to 8 p.m. Wednesday through Saturday. The menu also includes gelato and a dairy-free sorbetto. So Bambino's covers Mondays, when Jackson's is closed, and serves an early-evening sandwich crowd Jackson's never sees. Kraus has his own memory of this block. As a teenager he hung out with friends who worked at Coney Island, a hot dog stand that used to sit across the street from where Bambino's is now.
The Montana Club Took the Afternoon and the Late Night
Most new restaurants skip the hours between lunch and dinner. The Original Montana Club at 24 W. Sixth Ave. has rooms built for them.
The building dates to 1885. According to the Independent Record, it was the longest-running gentlemen's club of its kind west of Minneapolis. It opened to the public in 2018 and closed completely in 2024. California entrepreneur Ajitpal Pannu bought it and has spent $2.5 million reopening the six-story building floor by floor. Each venue is meant for a different kind of occasion. The club says three of those venues are open to the public: the Rathskeller, the Garden Room, and the 1885 Steakhouse.
- The Garden Room serves tea by reservation only, Friday from 2 to 6 p.m. and Saturday and Sunday from 10 a.m. to 4 p.m.
- The Rathskeller is the basement speakeasy that started the revival in May 2025. It has poker tables, a stage, and booths that reach out under the city streets, plus cocktails based on recipes from 1890s Helena bartender Julian Anderson. It opens at 3 p.m. Tuesday through Sunday. It closes at 10 p.m. Tuesday through Thursday, at midnight Friday and Saturday, and at 8 p.m. Sunday. It's closed Monday.
- The 1885 Steakhouse opened in June. Its page on the club's website doesn't list hours of its own, so check with the club before you plan a dinner around it.
General manager Samantha DeWit described the goal as pairing luxury with local access. Every venue except the private second-floor lounge is open to guests who aren't members. In practice, that means Jackson's closes at 3 and the Rathskeller opens at 3, just a few doors apart.
Benny's Took the Dinner Reservation
Benny's, at 108 E. 6th Ave., covers the last part of the day. New owner Derrick Quandt spent about a decade in food sourcing, including buying beans for a chickpea pasta company. "At the core, you notice, in a food system, you're always playing Walmart's game, Safeway's game," he told the Independent Record. "Benny's is us taking a more active role."
The restaurant reopened in early September. Executive chef Panayotis Tzinis visits Montana farms twice a week and rewrites the menu every week based on what he finds. The menu has six sections: amuse, larder, harvest, grain, the pot, and fire. Dishes are listed only by their ingredients, so the soup shows up as "bone broth, bread dumplings, aged cheese." Quandt expects most visits to cost $50 to $60 per person. Individual items run $12 to $20, and cooked entrees run $25 to $70.
The schedule is still changing. The homepage lists Thursday through Saturday dinner, but the reservation page shows dinner Wednesday through Saturday starting at 5:30 p.m., Chef's Table seatings on Wednesdays at 5:30 and 7:30 p.m., and Sunday Grazings from 5:30 to 8 p.m. Book through the reservation page instead of planning around one fixed night. Two dates are coming up this week:
- Wednesday, Oct. 7: a $95 Harvest Dinner, with arrivals from 5:30 to 7:30 p.m.
- Starting Thursday, Oct. 8: Prep Hour, Wednesday through Saturday from 4 to 5:30 p.m. through Nov. 21. Guests can watch the kitchen get ready for dinner service, often with a few small bites.
Prep Hour starts at 4, an hour after Jackson's closes, and that leaves almost no time of day on these two blocks without something open.
The Block, Hour by Hour
| Time | Where | Days |
|---|---|---|
| 10 a.m. to 3 p.m. | Jackson's Market and Deli, 32 W. 6th Ave. | Tue–Sat, per July reporting |
| 11 a.m. to 4 p.m. | Bambino's Deli, 330 N. Last Chance Gulch | Mon–Tue |
| 11 a.m. to 8 p.m. | Bambino's Deli | Wed–Sat |
| 10 a.m. to 4 p.m. | Garden Room tea, Montana Club | Sat–Sun, reservation only |
| 2 to 6 p.m. | Garden Room tea, Montana Club | Fri, reservation only |
| 3 p.m. to 10 p.m. or midnight | The Rathskeller, Montana Club | Tue–Sun; midnight Fri–Sat |
| 4 to 5:30 p.m. | Benny's Prep Hour, 108 E. 6th Ave. | Wed–Sat, Oct. 8–Nov. 21 |
| 5:30 p.m. onward | Benny's dinner | Check the reservation page |
Sixth Avenue has also become a place for events. Septemberfest, which ran Sept. 11–13 with the theme "Gulch Goes Galactic," held a soapbox derby down Sixth Avenue. Coordinator Vanessa Larson oversaw a weekend that also included more than 20 space-themed balloon sculptures, live music, and food trucks.
Off the Block, a Long Run Ends Saturday
On 11th Avenue, the news this week is a closing. Planet Gyros, at 1421 11th Ave., serves its last meals on Saturday, Oct. 10, after more than 32 years in Helena. Dennis O'Reilly has run it for the last 11 of those years. He and his wife, Pam, bought it in 2015, and his family had been eating there since 1995. Over time he moved the menu toward scratch-made soups, and he has a group of regulars who come in every Friday for chowder.
The pandemic years took the staff from seven people down to one. O'Reilly told the Independent Record that customers kept him going, leaving $100 bills for a single gyro, and that one anonymous $500 gift came with a note reading "We need you to stay in business." He said foot traffic never fully came back.
The space isn't going to sit empty like the downtown rooms did. Uphill Grill, a popular breakfast burrito stand, is taking over the lease. Planet Gyros staff are moving with it, and the opening is tentatively planned for the end of October. If that date holds, 1421 11th Ave. will switch from a lunch counter to breakfast service. Downtown's new lineup doesn't cover that slot, since nothing on the Sixth Avenue list opens before 10 a.m. That leaves this week for a last Friday chowder.
Cameron is based in Helena and follows changes like these closely, from a new deli in the old O'Toole's space to a 32-year lease changing hands, because they shape the blocks people live around. If you want to talk about what's changing near your own street, Cameron Hahn is happy to meet over lunch downtown. Schedule a free consultation.
