Community reigned supreme at the 2025 Best of Big Sky Awards at The Waypoint on Dec. 16. The annual event, hosted by Explore Big Sky and Outlaw Partners, gathered business owners, community leaders, nonprofits and even local pets to celebrate each other.
“At the end of the day a community is, by definition, all of us,” said Barbara Rowley. Joined on stage by Boyne Resorts President and CEO Stephen Kircher, Rowley accepted the “Community Member of the Year” award on behalf of her husband, Taylor Middleton, longtime Big Sky Resort leader. “We are all our community’s people of the year because there is no community of one, and being a part of this place has been a lifetime commitment for our family.”
By the end of the night, over 40 awards were handed out to deserving recipients, listed below. Explore Big Sky congratulates all nominees and thanks voters for making the annual tradition possible.
Best Lodging or Hotel: Montage Big Sky
Montage earned first this year for their offering of quality lodging with ski-in, ski-out access as well as a variety of year-round family-friendly activities. From s’mores and cooking courses, to their annual tree-lighting ceremony, bowling and fine dining, there’s a space for everyone just up the hill at the Montage Big Sky. montage.com/bigsky
2nd: 320 Guest Ranch
3rd: Lone Mountain Ranch
Best Vacation Rental Agency: Ascend Properties
Big Sky visitors rely on a solid rental agency for their experience. Ascend Properties, which took first in “Best Property Management” last year, continues its legacy with well-managed properties so that both guests and homeowners have the best experience possible. Ascend’s staff provides responsive, reliable service for vacationers getting a taste of the area, and they work to maximize revenue for homeowners who list with the company. ascendvacationrentals.com
2nd: Big Sky Luxury Vacations
3rd: Two Pines Properties
Best Property Management: Natural Retreats
The vacation rental market booms in Big Sky during the popular winter and summer months, and Ascend Properties ensures that all of their properties are well-managed, taken care of and that both guests and homeowners have the best experience possible. Their staff provides responsive, reliable service for vacationers getting a taste of the area, and Ascend works to maximize revenue for homeowners who list with the company. ascendvacationrentals.com
2nd: Big Sky Vacation Rentals
3rd: Two Pines Properties
Best Builder: Big Sky Build
Big Sky Build has been a common name for the “Best Builder” category. Led by John Seelye, the company has worked on Big Sky homes since 1997, holding a high value to communication, organization, teamwork and quality. Projects include Yellowstone Club homes and remodels, and custom builds throughout Big Sky, each complimenting the beautiful nature around them. bigskybuild.com
2nd: Ever-Green Roofing and Construction
3rd: Two Bear Construction
Best Architect: 45 Architecture
Longtime friends Jeff Lusin and Ben Erickson started 45 Architecture and Interiors in 2016 over a mutual respect for quality work and entrepreneurial spirit. Since then, their firm has grown to serve the Gallatin Valley and accommodate work with a human-first approach and a belief in its motto, “partnerships, not projects.” 45arch.com
2nd Center Sky Architecture
3rd Stillwater Architecture
Best Real Estate Agency: Outlaw Realty
With a solid foundation already built in Big Sky, Outlaw Realty is quickly becoming a trusted agency for buying and selling homes in the quickly growing Gallatin Valley and Bozeman region. OR’s team, which includes in-house experts in marketing, videography, operations and more, helps people streamline the home-buying and selling process to serve as their passport to the Western lifestyle. outlaw.realty
2nd Big Sky Real Estate Company
3rd Big Sky Sotheby’s International Realty
Best Realtor: Martha & Charlie Johnson
Martha and Charlie Johson bring over 30 years of combined experience to buyers and sellers of Big Sky homes. Agent and founders of Aperture Real Estate, a global real estate company, the mother-son duo are premiere advisors for luxury properties whether clients are buying or selling their next home. luxurybigskyhomes.com
2nd: Michael Pitcairn
3rd: Mia Lennon
Best Family-Friendly Activity: BASE Community Center
Operated by Big Sky Community Organization, BASE Community Center is truly a home base for all ages. A fitness center, gymnasium for pickup sports, a climbing wall, a child care center, and even an office space for BSCO and a host of community meetings, the building has gathered Big Sky folks for every occasion. BASE stands for “Big Adventures, Safe Environment” and many community members of all ages find themselves walking through the doors with an affirmation of the sentiment. bsco.org/base
2nd Big Sky Farmer’s Market
3rd Beartooth Pub & Rec. at the Montage Big Sky
Best Annual Event: Music in the Mountains
Music in the Mountains is perhaps the best summer tradition in Big Sky and while it has grown in popularity, it has kept its community ethos at close hand. Gathering music lovers from near and far at Len Hill Park, the Arts Council of Big Sky’s annual free summer music series brings musical talent of all genres to the stage for entertainment the whole family can enjoy. bigskyarts.org/pages/mitm
2nd Big Sky PBR
3rd Big Sky Farmer’s Market
Worth the Drive: Museum of the Rockies
Museum of the Rockies is a perfect, family-friendly mix of entertainment and education. At the Bozeman-based campus, visitors can explore exhibits that span hundreds of millions of years of Earth’s history from ancient geology and dinosaurs to the lives of Indigenous peoples and Montana pioneers, as well as a show at the Taylor Planetarium. Its endless lineup of visiting exhibits makes Museum of the Rockies worth the drive. museumoftherockies.org
3rd Stacey’s Bar
2nd MSU Sporting Events
Best Artist: Heather Rapp
From radiant wildflowers in the summer, to gold and orange aspen trees in autumn and majestic Lone Mountain in the winter, each season serves as an inspiration for local painter Heather Rapp. She finds color in just about everything, and when she’s not painting, you can find her snowboarding or serving up beers at Beehive Basin Brewery. heatherrapp.com
2nd: Jill Zeidler
3rd: Katie Riley
Best Photographer: Kevin Noble
Kevin Noble describes his approach to photography as minimalist, but the subjects he captures are huge: a 1,500-pound rodeo bull mid-buck, a towering, shaggy bison, or a geyser mid-eruption. Noble made the greater Yellowstone area his muse after a personal tragedy led him to seek a new life, and his black-and-white photography holds up a mirror to the grandeur of the West. kevinnoblephotography.com
2nd: Ryan Turner
3rd Caitie VanSloun
Best Local Musician or Band: Tuesday Night Rodeo Club
A trio featuring local music leaders Thad Beaty and his wife, Annie Clements, and Amanda Stewart, Tuesday Night Rodeo Club combines the best of Nashville with the best of the West. The group plays everything from country and Americana to classic rock and more, and can be heard around local venues including summer Tuesday rodeos at Lone Mountain Ranch, which inspired the group’s name.
2nd: Scavenger
3rd: Damnit Lauren!
Best Bar: Riverhouse BBQ & Events
A staple in Big Sky since 2013, Riverhouse BBQ & Events brings the slow-smoked flavor of Texas to Montana in both their food, drink and atmosphere. Founders Kyle Wisniewski and Greg Lisk met in 2003 while working as bartenders at the Half Moon Saloon (now The Riverhouse). Inspired by the deep sense of community and friendly neighbors, Wisniewski and Lisk set out to create a local hangout where family, friends and visitors could gather to prop their feet up on the back porch and enjoy a beer, views and barbecue. https://riverhousebbq.com/about/
2nd: Sccissorbills Saloon
3rd: Drunken Monk
Best Bartender: Thiago Arosteguy – The Waypoint
It’s one thing to mix a good drink, and it’s another thing to make every patron feel welcome. At The Waypoint, Thiago Arosteguy exemplifies hospitality with his attentiveness, helpful and kind attitude, and most of all, his signature sense of humor. Chat with him for just one minute and you’ll see why Big Sky voters awarded him “Best Bartender” this year. thebigskywaypoint.com
2nd: Joe Messreni
3rd: J.T. Kitchens
Best Chef: Michael Annandono – Michaelangelo’s Big Sky
While Big Sky is far from the Sicilian countryside, Michaelangelo’s owners Emily and Michael Annandono have been serving up delicious Italian cuisine in Meadow Village since 2016 and still today it is Big Sky’s favorite spot for a meal with your loved one or group of friends. Voted “Best Date Night” in the past, this year Chef Michael Annandono takes the prize for his finesse and attention to detail in Michaelangelo’s deserving menu. michaelangelosbigsky.com
2nd: Ian Troxler – Olive B’s
3rd: John Flach – BYWOM
Best Burger: BYWOM
BYWOM takes it again in 2025, not yet dethroned as Big Sky’s best burger. The BYWOM burger is a classic go-to for any occasion. Owners John and Pam Flach have been cheffing up burgers and other plates since the mid-1990s, while keeping the beloved establishment in touch with its truly local Westfork Meadows roots. While their burger has taken the award for years, the rest of the menu is worth a shop as well. bywombywordofmouth.com
2nd: Cafe 191
3rd: Riverhouse BBQ & Events
Best Coffee: Caliber Coffee Roasters
While new to the caffeine scene in Big Sky, Hero Snow in Meadow Village has quickly earned community love with their morning treats and carefully crafted coffees to kickstart a day or work of play. herosnowcoffee.com
2nd: Caliber Coffee
3rd: Cowboy Coffee
Best Pizza: Ousel and Spur Pizza Co.
After a first place win in 2023 and a second place win in 2024, Ousel and Spur Pizza Co. returned to the number one spot for Big Sky’s favorite pizza this year. Their specialty gourmet pizzas feature fresh house made sauces, hand tossed crust, and fresh vegetables from Montana farms..ouselandspurpizza.com/
2nd: Blue Moon Bakery
3rd: Milkies Pizza and Pub
Best Apres: Scissorbills Saloon
If you want to take a step back into time of dirtbag evenings of yore, grab a cold beer or a bite at Scissorbills Saloon after a long day of skiing. Their loyalty to the local ski community has made them a mainstay since Big Sky Resort first opened in 1973 and earned them “Best Apres” many years in a row. scissorbills.com
2nd: Beehive Basin Brewing
3rd: Horn and Cantle
Best Date Night: Blue Buddha Sushi Lounge
For a landlocked state, Blue Buddha Sushi Lounge provides guests with both delicious sushi and an intimate atmosphere for the perfect date night. The thoughtfully curated art paired with the traditional Japanese cuisine transports guests to a world outside Big Sky for a fun evening out. https://bigskybluebuddha.com/about-us
2nd: Horn and Cantle
3rd: Michaelangelo’s Big Sky
Editor’s Pick: The Landing at One&Only Moonlight Basin
When One&Only Moonlight Basin opened, placing Big Sky’s offerings on a global scale, The Landing, their first restaurant to serve the public, was highly anticipated. In the short time since then, they’ve earned our editor’s hearts and mouths over with their eclectic menu, all while overlooking the restaurant’s spectacular panoramic views. oneandonlyresorts.com/moonlight-basin
Best Local Meal Deal: Blue Moon Bakery
While Blue Moon Bakery is a repeat winner for their made-from scratch pies, this year they’ve earned a spot in “Best Local Meal Deal,” making it a go-to place for a bite whether it be for breakfast, lunch or dinner. The locally-owned bakery is a staple for classic pizza, pastries and specialty pies whether you’re looking for sweet or savory. bigskybluemoonbakery.com
2nd: Wrap Shack
3rd: Riverhouse BBQ & Events
Best Boutique/Gallery: Courtney Collins Fine Art
Courtney Collins Fine Art is a local gallery with acclaimed contemporary and traditional Western art from world-renowned artists. Featured artists include Kevin Red Star, Kenneth Peloke, David Yarrow and Ben Pease, and the gallery’s goal is to “preserve the heart of the Old West,” according to its website. courtneycollinsfineart.com
2nd: Montana Supply Co.
3rd: Rhinestone Cowgirl
Best Salon: Tribe Salon
Since 2017, Tribe Salon has been providing local hairstyling good enough to keep appointments booked weeks—and even months—in advance, and loyal customers coming back. Owner Hanna Powell is a longtime local and a ripping snowboarder, and her business is a fixture. facebook.com/p/TRIBE-SALON-100054544476687/
2nd: Ridge and Blade Barbershop
3rd: Hair Ninja
Best Spa: Santosha Wellness Center
Santosha Wellness Center’s services range from bodywork and massage, yoga and fitness classes, to rejuvenating Ayurvedic body therapies, and seasonal cleanses. The local business offers skin care services including various specialty facials—addressing customers’ specific concerns or their desire to “simply feel pampered and refreshed,” according to the website. For customers looking for something specific, chances are Santosha can provide it. santoshabigsky.com
2nd: Sanctuary
3rd: Spa Montage at Montage Big Sky
Best Wellness Business: Windy Ridge Chiropractic
A longtime business that changed hands in 2023, Big Sky’s Town Center chiropractor is now Dr. David Dalgardno. In his two-plus years in Big Sky, he’s quickly earned the trust of longtime patients and new walk-ins, especially outdoor athletes needing to get right for the next gnarly mission. windyridgechiropractic.com
2nd: Big Sky Natural Health
3rd: Moving Mountains
Best Cannabis Dispensary: Lone Peak Cannabis Company (LPC)
There’s no shortage of dispensary options in Big Sky, but the voters have spoken: Lone Peak Cannabis Co. is the favorite, yet again. Customers enjoy the LPClub loyalty program, especially with shops spread across the region in towns like Bozeman, Ennis, West Yellowstone, Lolo, Laurel and Butte. On the mountain, keep an eye out for ambassador athletes; they’re hard to miss in their LPC basketball jerseys. lonepeakcannabiscompany.com
2nd: Herbaceous
3rd: Java Joint
Leader in Sustainability: Gallatin River Task Force
The Gallatin River is a local gem, and Big Sky is lucky to have an organization dedicated to preserving its natural flow and character. From boots-on-the-ground projects to restore streambanks and ensure fishing access, to water quality monitoring and scientific studies to understand algal blooms and other environmental threats, the Gallatin River Task Force does more than many people may realize to protect Big Sky’s nearby waterway. gallatinrivertaskforce.org
2nd: Big Sky SNO
3rd: Big Sky Thrift
Best Outdoor Retailer: Gallatin Alpine Sports
When most residents think of a truly local ski, bike and gear shop, “GAS” comes to mind right away. Local owner Tom Owen is an avid biker and conservationist among other outdoor pursuits, and his staff knows their stuff across rentals, tunes, gear and accessories. For those wanting to support their local ski shop, GAS is a great option for a wide variety of sports. gallatinalpinesports.com
2nd: East Slope Outdoors
3rd: Montana Supply Company
Best Outfitter: East Slope Outdoors
Speaking of local shops, East Slope Outdoors has been locally owned since 1984 and bills itself as “Big Sky’s premier fly-fishing and ski shop.” Right on Town Center Avenue, the shop not only offers gear sales and rentals, but owner “Super Dave” Alvin and his staff are passionate about providing guided fly-fishing adventures, including the Gallatin, Yellowstone and Madison rivers. It’s a back-to-back award for East Slope! eastslopeoutdoors.com
2nd: Gallatin River Guides
3rd: Jake’s Horses
Emerging Entrepreneur: Heather St. Clair Ross – Sugar and Spice Florals
Specializing in weddings and events, but still offering everyday arrangements, Sugar and Spice Florals is the trusted provider of weekly florals for Montage Big Sky, as well as various restaurants and spaces in the community, according to its website. Owner Heather St. Clair Ross believes in “intricate simplicity,” and demonstrates a true passion for all things floral at her young, growing business. sugarandspicesflorals.com
2nd: Shannon Hyem and Ewan Knowles – Hero Snow Coffee
3rd: Jimmy Ensign – Jambo Designs Bike Racks
Best Dog In Big Sky: BSCO Parks and Trails Dogs – Sky, Louie, Angus, Finn | Lola | Goose (Three Way Tie)
We’ll keep it simple: being a good dog means more than just obedience. It’s about personality, flair, joy and kindness toward other dogs and us humans. Votes poured in for a whole lot of furry friends, and these are our top recipients. If one of them lives in your neighborhood, consider yourself lucky when you get the occasional chance to pet and play with these local all-stars.
Best Cat In Big Sky: Pico De Gato | Mable aka Space Kitten | Moxie
It’s hard not to vote for a cat named “Pico de Gato,” but “Space Kitten” isn’t a bad nickname either. While we haven’t met every cat on this list, it’s safe to say our third winner has some moxie. Every feline shares its own personality and lifestyle, whether we’re talking indoor cats, outdoor cats, cuddly cats or shy, cunning observers. Some, like Mable, are astronauts, too. Congratulations to these local favorites!
Best Restaurant: Horn & Cantle
Horn & Cantle Saloon at Lone Mountain Ranch serves plates that are perfect after a day in the snow. With fireside seating and Western style, guests can pop in for an appetizer and cocktails, or a hearty, delicious breakfast, lunch and dinner. lonemountainranch.com/horn-cantle/
2nd: Riverhouse BBQ & Events
3rd: BYOM
Best Nonprofit: Big Sky Bravery
Big Sky Bravery provides support to U.S. special operations forces post-deployment. Through all expense-covered trips in Big Sky’s serene landscapes, the nonprofit helps armed forces members transition from combat, reconnect with loved ones and forge new connections and decompress. bigskybravery.org
2nd: Big Sky Food Bank
3rd: Warriors & Quiet Waters
Best Women-Owned Business: Lone Peak Veterinary Hospital – Dr. Stephanie “Syd” Desmarais
“Dr. Syd” is surely a local hero, providing urgent and thoughtful care to countless Big Sky pets at Lone Peak Veterinary Hospital. Plus, she’s behind an effort to build a new clinic and animal shelter, which is currently under construction in the Westfork Meadow area. Even with the stress and energy required to run Big Sky’s only vet clinic, Dr. Syd keeps a smile on her face as she supports Big Sky’s pet-loving community. lonepeakvethospital.com
2nd: Big Sky Eyes – Dr. Erica Perlman
3rd: Shelly Bermont Fine Jewelry – Shelly Bermont
Editor’s Pick: Healing Hands Chiropractic – Dr. Andrea Wick
After recently moving into a new location in the Meadow Village Center, Dr. Andrea Wick continues to help patients reach their health and wellness goals. She holds a degree in kinesiology and human performance from the University of Wisconsin, with further education, experience and certifications in kinesiology and chiropractic care. She teaches healing classes and workshops including chakra healing, energetic boundaries, intuition and manifestation. drandreawick.com
Best Small Business (under 30 employees): Big Sky Print and Ship
Big Sky Print and Ship prides themselves on giving super-star customer care to everyone who walks through their door, and they’re known for their friendly employees and speedy service. Plus, it’s one of the only places in town that packages and ships goods and offers copying and printing. bigskyprintandship.com
2nd: Gallatin Alpine Sports
3rd: Big Sky Thrift
Editor’s Pick: First Tracks Tire Services
Providing oil changes, tire repair and brake service, First Tracks Tire Services are committed to high-quality, friendly care of Big Sky’s cars, helping out Big Sky residents with regular maintenance or when they’re in a pinch. firsttrackstire.com
Best Business (over 30 employees): Big Sky Ace Hardware
Big Sky ACE Hardware is known for its small town feel, good prices and helpful service. No matter what you need, the hardware store can point you in the right direction. acehardware.com/store-details/15730
2nd: Big Sky Land Management
3rd: Lone Mountain Ranch
Editors Pick: Big Sky Resort
Big Sky Resort earns Editor’s Pick this year for their commitment to year-round activities on snow and trail. With the opening of the gondola and Kircliff this winter, the progress on new and updated lifts continue to put Big Sky on the map, including SKI Magazine’s top pick for North American resorts in 2026. bigskyresort.com
Community Member of the Year: Taylor Middleton
For nearly 45 years, Taylor Middleton has been central to the long-term growth, vision and development of Big Sky Resort and its accompanying ski community. He began working for Big Sky Resort in 1981, rose to the executive level, and in September 2024, transitioned from his long-held role as president and COO into a strategic advisory role. It’s safe to say Middleton earned his spot on Big Sky’s Mount Rushmore of one-of-a-kind leaders.
2nd: Dr. Stephanie “Syd” Desmarais
3rd: Erik Morrison
Editors Pick: Laura Seyfang
Laura Seyfang’s local involvements are many: she was the first executive director of the Big Sky Community Housing Trust; she’s an officer for Big Sky Rotary Club; and she leads the Community Support Group, welcoming seasonal workers to Big Sky each winter with valuable connections and activities. Seyfang volunteers with a can-do attitude and is always looking for ways to give back to Big Sky.
