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The Real Reason to Visit Big Sky in the Fall (Hint: More Fun, Fewer People)

We know you’ve seen all of the stunning vacation photos that come out of trips to Big Sky, Montana—your cousins shredding fluffy white slopes in the heart of winter, or a TikTok of your aspiring influencer friend summiting a jaw-dropping mountain peak in the summer. Big Sky, Montana, is one of the best places to visit in the summer and winter, as our state is the ideal location for an outdoor getaway. 

But can you keep a secret? Lean in a little closer.

Fall’s actually the best time to visit Montana. 

We swear–it’s true! Between late August and early November, Big Sky and the surrounding areas transform into a fall wonderland. The Yellowstone crowd parks have faded away, and the air has lightly cooled, leaving the perfect playground for autumnal adventure. Picture cozy cabin vibes, yellow-leafed hikes, swing dancing under fairy lights, and peacefully fishing the Gallatin River in solitude.

That’s Big Sky in the fall.

In this blog, we’re going to let you in on the locals’ best secrets of why visiting Big Sky in the fall is the best choice you can make (and you can have the pics to prove it).

Why Big Sky in the Fall is One of the Best Kept Secrets 

Fall in Big Sky is like a secret level unlocked—quieter trails, golden views, and space to breathe (without sacrificing adventure). Here’s why locals love it and visitors in the know keep coming back this time of year:

  • Fewer People – With summer crowds gone and ski season still weeks away, fall gives you that rare “Montana to yourself” feeling. You won’t have to elbow your way into Yellowstone, wait in line for a latte, or battle for a dinner reservation in Town Center. It’s peaceful, it’s slow, and it’s exactly the kind of vacation pace you’ve been craving.
  • Stunning Fall Colors – The aspen and cottonwood trees show off in early to mid-fall, painting the mountainsides in glowing golds and fiery oranges. Whether you’re hiking, biking, or just sipping coffee on your cabin deck, the views are peak Instagram (no filters necessary). 
  • Mild Weather – Fall in Big Sky means crisp mornings, warm sunny afternoons, and cool sweater-worthy evenings. It’s the Goldilocks zone of Montana weather—not too hot, not too cold—making it perfect for outdoor adventure and cozy downtime.
  • Plenty of Activities to Enjoy – Just because it’s the off-season doesn’t mean it’s off-limits. You can still hike, bike, fish, horseback ride, golf, and even catch live music or farmers’ markets. Plus, the slower pace makes everything feel more spontaneous and relaxed. Want to grab a last-minute trail ride or cast a line at sunrise? No problem. Montana’s got your back.

Planning for Your Big Sky Fall Getaway

Convinced to experience Big Sky in its secret season? Great! Here are a few tips to help you plan the perfect autumn escape to Big Sky:

  1. Book Your Vacation Rental – Start by securing that cozy home-away-from-home. Fall may be the off-season, but Big Sky’s best cabins and condos can still book up, especially on weekends. Snag a vacation rental with a fireplace or hot tub for those chilly nights. After all, part of the fall charm is curling up comfortably after a day of adventure. Two Pines Vacation Rentals has a great selection of fall-friendly cabins complete with mountain views and modern amenities.
  2. Research Activities & Local Sights – Just because it’s quieter doesn’t mean there’s nothing to do. In fact, many summer activities are still in full swing through late fall. Plan out what you want to see and do: Will you hike to a waterfall, cast a fishing line, or take a day trip to Yellowstone? Check local calendars and business hours ahead of time. Some restaurants or tour companies scale back hours in the off-season, and Big Sky Resort’s big attractions (like ziplines or lift rides) usually pause until ski season. With a little research, you’ll know exactly what’s open, and you can line up activities in advance, ensuring you won’t miss any fall gems.
  3. Pack Layers – Montana fall weather can keep you guessing. Mornings start crisp (think frost on the meadow grass), afternoons warm up under that brilliant sunshine, and evenings cool off enough that you’ll want a sweater or light jacket. Pack breathable layers you can add or shed as the day goes on. Sturdy hiking boots are a must for trails that might be damp or muddy. And don’t forget a wool cap and gloves in case you catch an early-season snowfall on a high-altitude hike. (It happens!)

Best Activities to Do in Big Sky in the Fall

Hit The Trails

The trails are calling, and you’ll practically have them to yourself. Lace up your boots for famous hikes like Ousel Falls or Beehive Basin, which are even more magical decked out in fall colors. Without the summer throngs, you can snap uninterrupted photos of waterfalls and alpine lakes. We’ve even rounded up the top trails in our Big Sky hiking guide for some inspiration. Whether you choose an easy stroll to a waterfall or a day-long trek into the mountains, you’ll be rewarded with golden vistas and that crisp mountain air.

Try Casting a Line Cast

Ask any angler and they’ll tell you: autumn is prime time on the rivers. The Gallatin River (running right by Big Sky) transforms into an oasis of calm in the fall, with fewer fishermen competing for those choice fishing holes. Cool, clear water and active trout make for excellent fly fishing conditions. Local fly shops and guides are still open to set you up with gear or even take you on a guided trip, a great idea if you want to find those secret spots and get a primer on local hatches. A peaceful day of fishing in solitude (maybe with an eagle soaring overhead) is an iconic Big Sky fall experience.

Giddy Up with Horseback Riding 

Fall is a fantastic season for horseback riding in Big Sky. The trails are quiet, the scenery is stunning, and the weather is cool enough to keep you and your horse comfortable. Several local outfitters offer guided trail rides that wind through stands of aspens and across open meadows with Lone Peak looming in the distance. Whether you’re a seasoned rider or a total beginner, guides will match you with a trusty horse and lead you on an unforgettable mosey through Big Sky country’s autumn splendor. And yes, those Instagram pics of you on horseback with golden mountains behind will be epic.

Conquer the Mountain Biking Trails 

The cooler temps and occasional rain in Big Sky make for the perfect trail soil mountain bikers love. Try the local favorite Uplands/Hummocks loop near Town Center for a fun rolling ride through aspen groves, or take on the famed Mountain to Meadow trail, which descends from the ski area down into the Big Sky meadow with breathtaking views. You’ll find everything from gentle beginner paths to white-knuckle downhill runs (if you’re up for a challenge). For a deeper dive into the best trails and tips, check out our insider’s guide to Big Sky mountain biking.

Spot the Fall Colors & Wildlife 

If you’re a leaf-peeper or nature lover, Big Sky in fall will steal your heart. The surrounding forests explode in golds and oranges as aspens and cottonwoods reach peak color in mid-to-late September. Take a scenic drive down the Gallatin Canyon or up into nearby side roads like Taylor Fork. For an up-close view, hit a hiking trail or even just wander around Big Sky’s community parks; don’t forget your camera because every vista is postcard-worthy this time of year. 

Fall is also prime time for wildlife watching. As the weather cools, animals become more active all day long. You might spot elk herds grazing in open meadows or hear the eerie bugle of a bull elk echo in the evening. Deer are commonly seen nibbling in the dusk, moose might meander near creeks, and bears are fattening up before hibernation (so be bear aware and keep your distance if you see one).

Off-Road with an ATV Adventure

Craving a bit of throttle with your sightseeing? Fall is an awesome time to go off-roading in the Big Sky area. With an ATV or side-by-side UTV, you can access remote trails that climb into the mountains or deep into the forest, far beyond where the pavement ends. Several local companies offer rentals or guided ATV tours that will take you to wow-worthy viewpoints. By the end of the day, you’ll have a mud-splattered grin and maybe a new appreciation for just how big Big Sky country really is.

Cruise Through Crowd-Free Yellowstone National Park 

In the fall, America’s first national park truly shines. From Big Sky, it’s only about a 60-minute drive to Yellowstone’s West Entrance, making it an easy day trip. Fall in Yellowstone means fewer people (sometimes you’ll feel like you have the geysers all to yourself) and more wildlife on the move. September and October are great months to spot elk in the rut and to catch sightings of bison, pronghorn, bighorn sheep, or even wolves as they roam the valleys. The park’s landscapes get a gorgeous golden glow, and Old Faithful and the other geothermal features are still going strong. Whether you drive yourself or join a guided tour, visiting Yellowstone is absolutely worth it. 

Savor Local Cuisine and Cocktails

The beauty of visiting in the fall is that you can walk right into popular eateries that might require a reservation weeks in advance during peak season. Craving a bison burger, sushi roll, or farm-to-table bistro fare? Big Sky’s restaurants run the gamut, and, come autumn, you won’t have to fight the crowds to get a table. Many spots get creative with seasonal ingredients in the fall, so keep an eye out for daily specials featuring locally sourced squash, elk, or trout. 

Nothing tops off a crisp evening like a craft beer or warm cocktail. Big Sky has two local breweries (Lone Peak Brewery and Beehive Basin Brewery) serving up tasty pints. Rather have a cocktail? Order an Old Fashioned or a hot toddy and sip it by a crackling fire at one of the cozy lodges or bars around town. With the summer rush gone, the vibe at the bars is friendly and laid-back; you’ll likely end up chatting with locals or swapping adventure stories with fellow travelers.

Check Out Local Events & Entertainment

Big Sky’s “off-season” still has some fun up its sleeve. As autumn rolls on, the community comes together for a few special events that are worth planning your trip around. In late September, you can join the folks at Town Center for the annual Big Sky Oktoberfest celebration. It’s a relatively new tradition here, but growing fast. Picture a beer garden tent, German brats and pretzels, steins of local brews, live music, and even a wacky Lederhosen Fun Run costumed race to burn off those beers.

Come October, things get delightfully spooky with the Haunted Peaks Halloween Festival. For a weekend near Halloween, Big Sky transforms with haunted hayrides, costume parties for all ages (yes, there’s a dog costume contest too!), outdoor horror movie showings, and downtown trick-or-treating. 

Aside from these, you might find pop-up events like art workshops (fall-themed “sip and paint” nights or photography classes), community dances, or local theater performances, especially as folks get creative in the quieter months. Be sure to check the Big Sky events calendar before your trip to see what’s on. Even in the mellow season, this town loves to have a good time!

Enjoy a Cozy Night In

One of the true joys of Big Sky in the fall is the chance to slow down. After a day of adventures, you might find that your favorite evening activity is simply hanging out in your comfy cabin. Light up the fireplace, put on some soft tunes, and sink into the couch with a fluffy blanket. 

Many Two Pines vacation rentals come with entertainment options—big TVs for movie nights, game rooms, or shelves of board games. Whip up a hearty chili in your kitchen (there’s a great grocery store in town for supplies), or order takeout pizza, and then enjoy a feast in your pajamas. If you have a private hot tub, slip in for a soak under the stars. Montana’s night skies are incredible, and the cool fall air makes a steamy hot tub even more inviting. No noisy hotel neighbors, no schedule to keep, just the crackle of the fire and maybe the hoot of an owl outside. 

Find Your Perfect Fall Retreat

Ready to experience Montana’s best-kept secret for yourself? All that’s missing is the perfect home base for your autumn adventure. Two Pines Vacation Rentals offers a curated collection of Big Sky cabins, condos, and mountain homes that provide the ideal launch pad for all your fall fun. 

Want a secluded log cabin among the aspens? A luxe townhouse near Town Center so you can walk to eateries? Maybe a spacious lodge with a hot tub and panoramic deck for leaf-peeping right from “home”? No matter what your vision, we can help match you with a fall retreat that fits your group’s size, style, and budget. Plus, when you stay with Two Pines, you get local experts who can point you to the best trails, secret fishing spots, and local events. We love sharing our insider knowledge so you can experience Big Sky like a true Montanan.

Browse our Big Sky vacation rentals to find your perfect fall getaway and book early. Then pack your bags (don’t forget that sweater!), bring your sense of adventure, and get ready to see why autumn in Big Sky is the season so many wish they knew about sooner.

Here’s What Mountain Biking in Big Sky Montana Looks Like When It’s Done Right

We get that the phrase “it’s all downhill from here” has negative connotations. But when it comes to mountain biking, that phrase is the battle cry of the adrenaline seekers, the rush chasers, the “send it” professionals racing down brown pow mountain trails. And one of the #1 places you can find the best hero dirt in the country is Big Sky, Montana.

Our mountain trails are the kind that make your legs burn and your heart race in the best way possible. Whether you’re cruising smooth singletrack with your crew, navigating tight switchbacks solo, or taking on lift-served descents that demand a little grit (and a lot of brake control), mountain biking in Big Sky, Montana delivers the kind of rides you’ll be talking about all year.

So, clip in, gear up, and get ready to ride. Here’s everything you need to know to do mountain biking in Big Sky right.

Why Mountain Biking in Big Sky, Montana is Kind of a Big Deal

If you’re wondering whether Big Sky is really worth hauling your bike out (or renting one here), the answer is a very confident yes.

Big Sky is home to some of the best mountain biking trails in the West. Plus, they come with views so epic they’ll make you forget your quads are on fire. But it’s not just the terrain that makes this place shine. You’ll find local bike shops and rental pros who know their way around every spoke and switchback, plus guided rides, summer camps, and events that cater to beginners, daredevils, and everyone in between.

And when the day’s rides are done? You’ll have plenty of ways to relax. From local-favorite restaurants to vacation rentals with hot tubs, you can always find a great way to unwind in Big Sky. 

Step 1: Choose Your Trail, Choose Your Thrill

The perfect trip starts with the perfect trail. From beginner pedals to advanced adrenaline-chasers, Big Sky has a wide range of mountain biking trails to choose from. We’ve got the insider scoop on the best trails for your skill level. Here’s our curated selection of trails so you can get the best mountain biking experience possible.

Beginner Trails

Ousel Falls Trail – This wide, well-maintained trail winds 1.6 miles (one-way) through the woods to a stunning waterfall. With an average 4% grade, it’s a gentle ride suitable for all ages. You’ll pedal alongside the river and cross a couple of bridges before reaching Ousel Falls. (Pro tip: Start at the trailhead by Big Sky Town Center, and you can continue onto the flat Lone Peak and Gallatin Canyon trails for a longer ride.

Crail Ranch Trail – A 2.6-mile out-and-back cruise through Big Sky’s historic Crail Ranch meadow. This gravel path stays fairly flat and offers awesome views of Lone Mountain as you meander past wildflower fields and the local golf course. It’s a great “welcome to Big Sky” ride, not strenuous at all, and you can even stop by the Crail Ranch Homestead Museum along the way to add a dash of local history to your bike outing.

South Fork Loop – Don’t let the small distance fool you. This ~1-mile loop is perfect for new pedalers or an after-dinner leg stretcher. Located near Big Sky Community Park, the South Fork Loop is smooth and flat, tracing along a gentle creek. It’s essentially a scenic victory lap for new riders to build confidence in an idyllic setting.

Intermediate Trails

Hummocks Trail (Loop) – A 3-mile rolling loop that’s all about flowy fun. “Hummocks” refers to the bumpy mounds shaped by ancient landslides, and this trail swoops you up and over these mini-hills through aspen groves and two small wetlands. With gentle ups and downs, it’s an entertaining ride that gives you a little workout without any monster climbs. There are three interconnecting lollipop loops, so you can shorten or extend your ride as you please. Located just a mile from Town Center, Hummocks is a favorite among locals for a quick after-work ride. 

Mountain to Meadow Trail – Arguably Big Sky’s most iconic ride, this ~5.5-mile trail starts near the base of Big Sky Resort and descends all the way to the Meadow Village. It winds through open wildflower meadows, aspen groves, and shady forests with jaw-dropping views of Lone Peak looming above. Difficulty-wise, it’s a solid moderate: doable for intermediates and ambitious beginners (especially if you take it slow). Many riders maximize the downhill by taking a lift or shuttle up to the resort, then coasting down Mountain to Meadow’s glorious flow..

Mud Creek Loop – This 3-mile loop, just south of Big Sky off Highway 191, is a beginner-friendly singletrack that most would rate as solid intermediate due to a short climb. The first half gains about 450 feet—enough to get your blood pumping—then it’s all smooth sailing downhill. The descent is a blast, with bermed turns and gentle rollers that put a huge grin on your face. Local tip: Ride it counter-clockwise for the best experience (climb up the steeper side and cruise down the flowy side).

Advanced Trails

Cinnamon Mountain Trail – If you’re looking for a true backcountry adventure, Cinnamon Mountain delivers. With a long, steep climb and loose, rocky sections, this out-and-back trail rewards seasoned riders with panoramic views at the summit and a wild, fast-paced descent. It’s remote, rugged, and absolutely worth the grind.

Buck Ridge Trail – This long-distance ridge ride gives you the feeling of flying across the spine of the mountains. While technically less gnarly than others, it’s a physical challenge thanks to the exposed terrain, shifting elevation, and sheer length. It’s best tackled on a day with perfect weather..

Garnet Mountain Trail – A short but spicy ascent leads to one of the most stunning lookouts in the area. The descent? Steep, technical, and wild enough to satisfy even the most hardcore riders. Bonus points if you climb to the lookout for an unbeatable mid-ride photo op (and a breather).

Step 2: Check Out Big Sky Resort Mountain Biking

Want to skip the climb? Big Sky Resort mountain biking turns gravity into your best friend. With a Bike Haul Pass, you can load your bike onto the Ramcharger 8 or Swift Current 6 chairlifts and access over 40 miles of downhill and flow trails—from smooth beginner runs to epic expert lines. 

What Makes Bike the Sky Special

Big Sky’s creative trail crew now offers “Bike the Sky” signature routes—curated intermediate-to-advanced descents that combine hidden gems and local features in one epic ride.

  • The Intermediate route flows from Swift Current through Tango, Last Waltz, Flicker, Soul Hole, Gambler, and wraps up with Happy Hooves via Ramcharger 8.
  • The Advanced route includes parts like E.L.S.H, Ninja Marmot, and Sneaky Weasel for seasoned riders chasing airtime.

Beginner-Friendly Bike Park Options

New to resort biking routes? Try smooth runs like Happy Hooves or Easy Rider, which offer flowy terrain ideal for beginners or those easing into downhill Big Sky style. Even better, Big Sky often runs a Women’s Bike Skills series, a friendly, progressive clinic with an all-female coaching team, welcoming complete beginners to pros. They also offer downhill lessons (private or group), including junior clinics and youth bike camps.

Step 3: Time it Right

Plan to ride early in the day if you can. Morning rides mean cooler temps, smoother trail conditions, and a better chance to spot wildlife like deer or moose on the quieter trails. Not a morning person? Late afternoon/early evening can be lovely too, once any storms pass. Just avoid the mid-day scorchers in July and August.

Step 4: Save the Hassle and Rent Your Gear Here

You don’t need to haul your own bike to Big Sky. The local shops have more than enough for you, your friends, and any friends you make along the way. Gallatin Alpine Sports in Big Sky Town Center is a go-to for high-quality mountain bike rentals, tune-ups, and gear (they’ll set you up with the perfect ride for Big Sky’s rugged terrain). Up at the resort, Different Spokes bike shop offers convenient rentals right by the lifts, plus any spare tubes, parts, or advice you might need. These folks are riders themselves, so don’t hesitate to ask for trail recommendations or current conditions. If you did bring your own bike and something goes clunk, shops like GAS or Grizzly Outfitters can save your vacation with a quick repair.

Step 5: Connect with the Community (We’re Nice, We Promise!)

One of the best parts of mountain biking in Big Sky is the local biking community. Check out group rides or weekly races if they line up with your visit. The Big Sky MTB scene is super welcoming. The Big Sky Community Organization (BSCO) and Southwest Montana Mountain Bike Association often host trail days and group outings. Even if you’re flying solo, you might bump into friendly locals on the popular trails. Don’t be shy about asking for a favorite trail suggestion; Big Sky bikers love sharing their stoke and might just tip you off to a secret singletrack or two.

Step 6. Make Your Mom Happy: Don’t Forget Safety Essentials

Montana is wild country (just ask the bears and mountain lions), so a bit of preparation goes a long way:

  • Always wear a helmet. Nope—no exceptions. Body armor (knee/elbow pads) is smart if you’re tackling rocky or high-speed trails, especially at the bike park. 
  • Carry a trail map or have an offline map app, since cell service can be spotty in the woods. 
  • Bring a small first aid kit for scrapes and a multitool for minor bike fixes. 
  • Bear spray is a must on virtually all Big Sky trails outside the resort. Keep your spray accessible (and know how to use it) just in case.
  • Ride with a buddy or make noise around blind corners to avoid surprise encounters. 
  • Adhere to basic trail etiquette: yield to hikers and uphill riders, don’t skid around corners (it causes erosion), and pack out your trash.

Step 7: Stay Hydrated & Altitude-Aware

Big Sky’s trails sit at around 6,000+ feet in elevation. That thin air will sneak up on you if you’re visiting from lower elevations. Drink plenty of water before and during your ride. Take breaks as needed, and don’t be embarrassed to catch your breath and enjoy the view (we’ve all been there, gasping “I swear I’m in shape at sea level!”). A couple of days of acclimation and you’ll be tackling those climbs like a champ

Step 8: Pick the Best Après-Ride Eats

After conquering the trails, you’ll have a serious appetite. Good news—Big Sky’s dining scene has restaurants to match every post-ride craving. Hit up Ousel & Spur Pizza Co. for creative, stone-fired pizzas, or grab some Montana-signature burgers and steaks at Corral Bar & Steakhouse. Looking for something a little more upscale (and with killer cocktails)? Check out Horn & Cantle, the upscale saloon at Lone Mountain Ranch. Taco lovers can refuel at Tres Toros in Town Center with street tacos and margaritas. For a quick bite or breakfast-for-dinner vibes, Blue Moon Bakery is a local favorite for sandwiches, baked goods, and beer on tap. One thing’s for sure: you won’t go to bed hungry in Big Sky.

Step 9: Rest Your Head (& Helmet) at a Two Pines Vacation Rental

After a day racing up and down the trails, you’ll need a comfortable home base where you can rest your muscles…and maybe order in food if you can’t walk quite yet. Two Pines Properties has your back (and your sore legs). 

We offer a range of Big Sky vacation rentals that feel just like home, the kind of place where you can prop your bike in the mudroom or garage, lounge on a deck with a view, and recount the day’s thrills over a cold drink. Our properties are set up with bikers in mind: spacious garages and storage areas for your bikes and gear, in-unit washers/dryers to refresh your dusty kit, and cozy living spaces to stretch out in. Many of our properties even come with private hot tubs, the perfect reward for your legs and back after a long ride. 

Even better, our rentals are super close to the action. You’ll be minutes from trailheads, Big Sky Resort, and the best restaurants to grab a post-ride bite. And if you have any questions or want some local insider tips, our team lives here in Big Sky. We ride these trails (before work, after work…and maybe on our lunch breaks too). We’re more than happy to swap trail tales and point you to the perfect ride.

Book Your Mountain Biking Escape Today

Don’t settle for anything less than the perfect mountain biking retreat. Book your stay with Two Pines Properties and get access to the best, biker-friendly lodging that keeps you close to the trails and all the perks. Browse our selection of Big Sky vacation rentals today and get ready to shred the trails—Montana-style.

5 No-Filter-Needed Big Sky Hikes to Add to Your “Must Visit” List

Take a hike? Don’t mind if we do (especially if the hike is in Big Sky!). 

Big Sky, Montana is a paradise for hikers, especially as the snow melts and the wildflowers start to bloom. The scenes are breathtaking, and not just because of the high altitude. Whether you’re a seasoned trekker or just looking to stretch your legs and take in the views, there’s a trail for everyone here—if you know the right places to look. 

So you have the best inside scoop for your Montana trip, we’ve curated a list of the top Big Sky hikes locals of all skill levels love to trek and photograph. These five trails are close to town, showcase the Big Sky state’s epic beauty, and get you those Instagram-worthy photos your friends will be jealous of for years to come. 

5 Scenic Big Sky Hikes That Stun IRL

1. Ousel Falls Trail (Easy)

This Big Sky favorite is short, scenic, and beginner-friendly. The trail winds through a shaded forest alongside the South Fork of the West Fork of the Gallatin River and ends at a roaring 30-foot waterfall. At just 1.6 miles round-trip with minimal elevation gain, it’s perfect for families or anyone easing into hiking season.

2. Beehive Basin Trail (Moderate)

Arguably the most iconic summer hike in Big Sky, Beehive Basin delivers everything you want in an alpine hike: wildflowers, mountain views, and a serene glacial lake. The 6.6-mile out-and-back trail gains around 1,500 feet, making it a manageable but rewarding trek for most hikers.

3. Lava Lake (Moderate)

Located just outside of Big Sky in Gallatin Canyon, the Lava Lake trail is a shaded, steady climb that pays off with a sparkling alpine lake surrounded by rock walls. The 5.5-mile round trip gains about 1,600 feet in elevation. Pack a snack and take a dip if you’re brave—the water stays cold!

4. Storm Castle Peak (Challenging)

Looking for a workout with a jaw-dropping view? Storm Castle offers a steep, switchback-filled hike up to panoramic views of Gallatin Canyon and the surrounding peaks. It’s about 5.2 miles round-trip with 1,800 feet of elevation gain. Best for experienced hikers whose calves are up for a challenge (trust us, the views and photos are worth the trek).

5. Uplands and Hummocks Trail Loop (Easy to Moderate)

Just minutes from Big Sky’s Town Center, this trail network gives you flexibility and lovely views without committing to a long hike. You can do a quick 2-mile loop or combine trails for something longer. It’s ideal for atmospheric photos of sunset strolls, trail running, or a spontaneous afternoon outing.

Real Hikers Stay with Two Pines Properties

If you’re planning hiking adventures in Big Sky, where you stay matters. After a day of switchbacks and sore muscles, you don’t want to fight for parking or have the chatter from the room next to yours disturbing your sleep. You need a home with easy access to the best hikes and a relaxing place to rest after you’ve worked up a sweat on the trails.

Two Pines Properties offers vacation rentals that put you close to the trailheads while giving you space to relax and recover after your trek. With hot tubs to soothe tired muscles, decks with mountain views, and locally owned service that knows the area’s trails inside and out, we’re the ideal home base for outdoor enthusiasts.

Book Your Summer Hiking Getaway

What are you waiting for? Big Sky’s trails are calling—and Two Pines is ready to welcome you! Browse our vacation rentals and book your summer escape today to enjoy nature’s best with all the comforts of home.