Southwest Billings Runs Its Summer Around a 108-Year-Old Hill and a Tuesday Night Concert

On a Tuesday evening in late summer, the amphitheater at Josephine Crossing fills in the way it always does: lawn chairs staked out an hour early, a line at the food truck, kids chasing each other around the edge of the crowd while a local band tunes up. It looks like the kind of scene a master-planned neighborhood pays a marketing firm to invent. It isn't. It's a volunteer-run concert series that's been happening on and off since 2017, and this season's lineup includes Juliette Angelo and the Heartaches with opener Jillian Nordberg, the proceeds going to Love and SONshine Ministries, one of a rotating cast of local nonprofits the series has supported over the years, from CASA of Yellowstone County to the Songbird Community Garden to the Yellowstone Boys and Girls Ranch.

Ten minutes south, past Blue Creek Road, sits a hill that has nothing to do with any of that. It's rutted, steep, and named the Bentonite Nightmare, and it has been humbling motorcycle riders since 1918. The Billings Motorcycle Club runs the Great American Hill Climb there every summer, and the 2025 running was the 107th consecutive year the event has happened. That means the hill predates Josephine Crossing, Annafeld, Briarwood, and pretty much every other name residents associate with this part of town, by nearly a century.

That's the thing about Southwest Billings that doesn't show up on a map of new subdivisions: the neighborhood's summer calendar isn't organized around what's newest here. It's organized around what's oldest, with the new developments filling in the space around it.

The Newest Part of the Neighborhood Still Runs on a Decades-Old Format

Josephine Crossing is the kind of development real estate marketing usually leans on hard: walkable streets, pocket parks, a mile of trail along the Yellowstone River. What doesn't get mentioned as often is that the neighborhood's actual social glue is a free concert series held at an outdoor amphitheater, running Tuesdays through the summer from 5 to 8:30 p.m., with each show benefiting a different local cause. Food trucks and a beer and wine tent show up every week, and organizers ask attendees to leave dogs at home given how packed the amphitheater gets. Parking is street-only, with the overflow lot running south along the river, which is a detail that matters more than it sounds like it should if you're planning to show up after 5:15.

The format hasn't changed much since the series started. It isn't a festival with headliners and ticket tiers. It's a neighborhood passing a bucket for a school PTO or a food pantry while a local act plays 70s-style soul or country covers. That consistency is arguably the point. New subdivisions get built with a five-year plan for parks and amenities. This one built a weekly ritual instead, and residents have kept showing up for it for the better part of a decade.

A Hill That's Older Than Every Subdivision Around It

If Josephine Crossing represents what's new in Southwest Billings, the Great American Hill Climb represents the opposite end of the timeline. The Billings Motorcycle Club has been running hill climbs at its grounds on Old Blue Creek Road since before Montana had paved highways connecting most of its towns, and the event has earned a reputation as one of the largest and richest motorcycle hill climbs in the country. Riders travel in from across the United States to attempt the Bentonite Nightmare, a climb built from bentonite clay, shale, and gumbo that changes texture depending on how much it's been watered that week. The professional purse has run into the tens of thousands of dollars in recent years, and past champions have included multiple riders with Billings addresses, which gives the event a hometown-pride element that a lot of motorsport spectacles don't have.

What's notable for anyone living nearby isn't just the scale of the event. It's the location. The hill climb happens in the same South Hills stretch of Southwest Billings where Blue Creek Elementary and the sport shooting range sit, land that looks rural on a map but is a short drive from Josephine Crossing's front gate. The neighborhood contains both the newest planned community in the city and one of its oldest continuously run sporting traditions, separated by a few miles of road.

The Golf Course You Don't Need to Join

Briarwood Golf Club sits just south of Interstate 90 and has been rated among the top courses in Montana by Golf Digest more than once since it opened in the mid-1980s. It's a private club, which is the detail that tends to stop people from ever walking through the door. What doesn't get advertised as clearly is that the Black Bunker Bar & Grill, the restaurant attached to the clubhouse, is open to the public. You don't need a membership to sit on the deck, order dinner, and watch the course roll out toward downtown Billings in the distance. For a neighborhood built around golf-course views in its marketing materials, that's a useful thing to actually know: the dining room with the best sightline in Southwest Billings doesn't require joining anything.

Between the Big Nights

Not every evening in Southwest Billings involves a concert or a motorcycle. Most of the actual daily rhythm happens in smaller places, and Annafeld, the newer McCall Homes development about a mile west of Josephine Crossing along the river, has become one of the spots where that rhythm shows up. The neighborhood mixes single-family homes with townhomes and a small commercial corridor along Elysian Road, including live-work units where residents can run a business on the ground floor and live upstairs. Maple Moose Coffee and Pop Shop opened as part of that stretch and has settled into the role of informal gathering spot, the kind of place where a coffee run turns into a ten-minute conversation with a neighbor.

None of this is dramatic. That's the point. Between the Tuesday concerts and the summer hill climb, the actual texture of life here is a coffee shop, a golf course restaurant that doesn't require a membership card, and a river trail that connects most of it on foot.

What Ties It Together

It would be easy to write Southwest Billings off as just a collection of new subdivisions stitched together along the Yellowstone River, and a lot of the marketing copy for individual developments encourages exactly that reading. But the neighborhood's actual identity gets built somewhere else. It's built at a hill that's been challenging riders since before most of the streets around it existed, and at an amphitheater where a rotating cast of local nonprofits gets a Tuesday night spotlight every summer. The new construction gives people a place to live. The older institutions are what give the area something to organize a summer around.

If you already call this part of Billings home, none of this is news exactly, but it's worth noticing how much of what makes the neighborhood feel like a neighborhood traces back to things that were here long before the newest cul-de-sac got its name.

If you're ever curious what your home in Southwest Billings would sell for in today's market, or just want to talk through what's changing in the area, the team at Live.Laugh.Montana. is happy to help. You can get an instant home valuation and schedule a consultation anytime. Until then, we'll see you at the amphitheater on Tuesday.