Billings is the kind of place where a weekend with friends turns into an adventure without much effort. The city sits between sandstone cliffs, open prairie and the Yellowstone River, making it a natural basecamp for hiking, fishing, exploring and good food at the end of a long day outdoors. With rugged landscapes minutes from downtown and a growing craft beer and restaurant scene, Billings offers the ideal mix of outdoor adrenaline and laid-back evenings. Over four days, a guy’s getaway here unfolds across cliffside trails, historic landmarks, and long dinners that stretch late into the night.
3 p.m. Check in and head for the Rimrocks
Drop your bags before heading straight to Zimmerman Park. Sitting along the Rimrocks that frame the city, the park offers cliffside trails and panoramic views across the Yellowstone River Valley. A short hike along the sandstone edges gives you a feel for the wide-open landscape that defines this part of Montana. Locals often gather here in the late afternoon to watch the sun dip toward the horizon.
6 p.m. Explore the Billings Brew Trail
Exploring the Billings Brew Trail with friends turns an ordinary night out into an easygoing adventure through the city’s craft beer scene. The trail boasts 10 breweries, two distilleries, a cider mill and a winery. Many of the stops are along a 1.5-mile loop through the historic downtown region, while others allow you to explore beyond the downtown core and broaden your Billings experience. Be sure to stop in at Undammed Distillery and check out the Billings-only bourbon released in 2025 – Pryor Creek Bourbon. It’s literally a bourbon you won’t find outside of Billings.
Food is part of the experience as well. Some breweries offer full menus with burgers, pizzas or shareable appetizers, while others regularly host food trucks parked just outside the taproom doors. It is easy for a group to grab a round of beers alongside baskets of fries, flatbreads or hearty pub fare, making each stop feel like its own casual hangout spot.
8 a.m. Breakfast at Bernie’s Diner
Start the day with a classic diner breakfast at Bernie’s Diner, a longtime Billings favorite known for its retro atmosphere and generous portions. Inside, chrome stools line the counter and cozy booths fill the dining room as locals gather over steaming mugs of coffee and hearty morning plates.
The menu features all the comforting breakfast staples needed to fuel a full day of adventure, from fluffy pancakes and omelets loaded with fresh ingredients to breakfast sandwiches and crispy hash browns. Friendly service and a laid-back vibe make it an easy, satisfying way to kick off the morning before heading out to explore the wide-open landscapes around Billings.
9:30 a.m. Rock climbing at Acton Recreation Area
Acton Recreation Area offers sandstone cliffs and climbing routes overlooking open prairie. The rugged setting feels remote even though it is close to town. Climbers will find a variety of routes across the cliff faces, while others can scramble among the rock formations and take in sweeping views of the surrounding landscape. The contrast between the red sandstone cliffs and the rolling prairie below creates a dramatic setting that feels distinctly Montana.
For those who need gear or local advice before heading out, stop by Steepworld Climbing & Fitness. The climbing gym and outdoor shop is a hub for the local climbing community and a great place to gather route information, conditions and safety tips for the Acton area. Visitors can rent equipment such as harnesses, shoes and ropes, or connect with experienced climbers who know the local routes. Staff are happy to point newcomers toward beginner-friendly climbs and explain what to expect at the site.
1 p.m. Lunch at The Divide Bar & Grill
After a morning outdoors, stop for lunch at The Divide Bar & Grill, a laid-back spot known for its hearty comfort food and welcoming Montana vibe. The restaurant blends a casual sports bar atmosphere with a menu full of satisfying options that hit the spot after a morning of climbing or exploring.
The menu features classic favorites like stacked burgers, sandwiches, wings and baskets of crispy fries, along with cold beers on tap that make it easy to relax and refuel. Large portions and a lively dining room make The Divide a great gathering place for groups, where friends can swap stories from the morning’s adventure before heading back out to explore more of Billings and the surrounding landscape.
3 p.m. Fly fishing on the Yellowstone River
In the afternoon, head toward the Yellowstone River, one of the most iconic waterways in the American West and the longest undammed river in the contiguous United States. Just minutes from downtown Billings, anglers can access long stretches of river where clear currents wind through cottonwood groves and open prairie. The river is known for healthy populations of rainbow and brown trout, making it a favorite destination for fly fishing enthusiasts.
Depending on the group’s experience level, visitors can fish from the banks, wade into slower-moving sections or arrange a guided float trip that drifts through scenic stretches of the river. Floating the Yellowstone offers a unique perspective of the landscape, with sandstone cliffs, wildlife and wide Montana skies unfolding along the route.
For gear, guidance and rentals, stop by East Rosebud Fly & Tackle, a well-known outfitter among local anglers that offers fly rod rentals, waders, flies and other essential equipment. Staff also can provide up-to-date information on river conditions, recommended fishing spots and techniques for the season. Guided trips are available as well, giving visitors the chance to learn from experienced anglers who know the Yellowstone’s currents and trout patterns.
You also can gear up at SCHEELS in the West End. SCHEELS is more than a sporting goods store. It’s a destination experience for locals and visitors alike. The massive two-story, 220,000-square-foot store features Montana’s largest selection of sporting gear, outdoor equipment, apparel and footwear, making it a go-to stop for everything from fishing and hunting to hiking and fitness.
7 p.m. Dinner at TEN at the Northern
End the day with dinner at TEN, the signature restaurant inside Northern Hotel, one of downtown Billings’ most iconic historic properties. The restaurant blends classic steakhouse tradition with a modern Montana sensibility, making it a fitting place to unwind after a full day of outdoor adventure.
The menu focuses on premium steaks, fresh seafood and thoughtfully prepared sides. Guests often start with shareable appetizers before moving on to expertly grilled cuts of beef, seasonal dishes and house specialties that highlight regional ingredients. The polished dining room, warm lighting and attentive service create an atmosphere that feels upscale but still relaxed enough for a group dinner.
8:30 a.m. Coffee and breakfast at McCormick Cafe
Start the morning at McCormick Cafe, a longtime downtown Billings favorite known for its no-frills atmosphere and classic diner-style breakfast. Early risers and regulars fill the booths while the smell of fresh coffee and sizzling breakfast plates drifts from the kitchen.
The menu focuses on hearty morning staples that are perfect before a day of exploring, including eggs cooked to order, bacon, hash browns, pancakes and breakfast sandwiches. Strong coffee keeps the table refilled while friends ease into the morning and map out the day’s plans. It is the kind of authentic local stop that gives visitors a taste of everyday Billings before heading back out onto the road.
10 a.m. Biking at Swords Rimrock Park
Start the morning with a ride along the trails at Swords Rimrock Park, one of Billings’ most scenic places to explore on two wheels. Perched along the sandstone Rimrocks that overlook the city, the park offers paved paths and rugged dirt trails that follow the edge of the cliffs, delivering sweeping views of the Yellowstone River Valley below.
Cyclists can cruise along the Rimrock Road corridor or venture onto nearby trail networks that weave through prairie grasses and rocky outcrops. The elevated vantage point provides a dramatic perspective of Billings, with the city stretching across the valley floor while wide-open Montana landscapes unfold toward distant mountain ranges.
For those who need bikes or gear, visitors can rent equipment from local outfitters such as The Spoke Shop, which offers bike rentals, helmets and local trail advice. Starting the day with a ride along the Rimrocks is a great way to take in Billings’ signature landscape while getting one more dose of adventure before the weekend wraps up.
12:30 p.m. Lunch at Montana Brewing Company
Lunch at Montana Brewing Company offers a relaxed midday break in the heart of downtown Billings. The longtime local favorite pairs a lively brewpub atmosphere with a menu built for hearty appetites. Guests can choose from wood-fired pizzas, stacked burgers, sandwiches and fresh salads while sampling a rotating lineup of house-brewed beers, from crisp lagers to bold IPAs. Large tables and a bustling dining room make it an easy place for groups to gather, refuel and swap stories from the morning’s adventures before heading back out to explore more of Billings.
1:30 p.m. Tee It Up
Golfing in Billings offers a chance to play beneath Montana’s wide-open skies while surrounded by dramatic Western landscapes. The city is home to several public courses, where rolling fairways, tree-lined holes and views of the nearby Rimrocks create a setting that feels distinctly Montana. With welcoming clubhouses, scenic layouts and an easygoing atmosphere, golf in Billings blends sport, scenery and the unhurried rhythm of a Montana getaway.
7 p.m. Dinner at Montana Rib and Chop House
Settle in for dinner at Montana Rib and Chop House, a classic Montana steakhouse known for its hearty portions and Western hospitality. The restaurant’s warm, rustic atmosphere makes it an ideal gathering spot for groups looking to relax after a full day of exploring.
The menu highlights the kinds of bold, satisfying dishes the region is known for, including slow-roasted prime rib, grilled steaks, fall-off-the-bone ribs and fresh seafood. Shareable appetizers, generous sides and a solid lineup of beers and cocktails make it easy to linger at the table while swapping stories from the day’s adventures.
9 p.m. Speakeasy drinks at The Waiting Room
Finish the night with craft cocktails at The Waiting Room, a hidden Prohibition-style speakeasy tucked away in downtown Billings. The intimate bar is designed to evoke the feel of the 1920s, with low lighting, vintage décor, marble-topped tables and classic jazz often playing softly in the background.
Bartenders here take their craft seriously, mixing carefully balanced cocktails that range from timeless classics like Old Fashioneds and Manhattans to house creations featuring unexpected ingredients and premium spirits. Guests typically settle into leather chairs or gather around small tables, where conversation flows easily and the pace of the evening slows down.
8:30 a.m. Breakfast at Sophie’s Kitchen
Ease into the final day of the trip with a relaxed breakfast at Sophie’s Kitchen, a welcoming local café known for its comforting breakfast plates and friendly neighborhood atmosphere. The dining room fills early with the aroma of fresh coffee and sizzling breakfast skillets as locals settle into booths and gather around tables to start the morning.
The menu features hearty favorites like fluffy pancakes, omelets packed with fresh ingredients, breakfast sandwiches and crispy hash browns. Many guests opt for one of the café’s classic breakfast platters, pairing eggs and bacon with warm toast and plenty of strong coffee.
10 a.m. Explore Phipps Park and disc golf at Diamond X Disc Golf Course
Start the morning at Phipps Park, a rugged outdoor recreation area where sandstone cliffs rise above rolling prairie and open trails stretch into the surrounding hills. The park is popular with hikers, mountain bikers and trail runners, offering a quiet setting that feels far removed from the city.
From Phipps Park, head over to the nearby Diamond X Disc Golf Course, one of Billings’ most well-known courses. Set among rocky terrain, juniper trees and sweeping Rimrock views, the course offers a fun challenge for both experienced players and newcomers. Long drives, elevation changes and wide-open fairways make each hole feel like its own small adventure, with the surrounding landscape providing dramatic scenery along the way.
1:30 p.m. Lunch at Captain Scurvy’s Black Dragon
Wrap up the trip with a laid-back lunch at Captain Scurvy’s Black Dragon, a unique local spot known for its bold flavors and pirate-themed atmosphere. The restaurant has built a reputation for creative takes on comfort food, especially its loaded sandwiches and hearty plates that satisfy big appetites after a morning of adventure.
Guests can choose from stacked sandwiches, flavorful seafood options and other casual favorites, often paired with cold drinks and generous sides. The playful décor and relaxed vibe make it a fun final stop for a group of friends.
