Group of cowgirls riding on a field with a forest behind them.

Cowgirl Fall Roundup: Ride and Reel

September 11 – 14, 2026

Adventures in the Saddle and Along the River

There’s a little cowgirl in all of us, whether we live in Montana or on Madison Avenue. That’s why we love celebrating the horsewomen among us, the ones who take the reins, push boundaries, and inspire us with their can-do attitudes and awesome determination.

We’ve been rounding up our favorite cowgirls every spring for nearly a decade, and our unbridled enthusiasm for these horse-backing heroines has led us to add another event in the fall. Now, you can ride and fly fish along with these legendary women in the crisp air and golden glow of autumn in Montana.

Experience a thrilling rush of adrenaline as you saddle up for exhilarating equestrian adventures, and find your inner peace as you fly fish along Montana’s tranquil rivers. Join us for a one-of-a-kind, three-day journey alongside Cowgirl Hall of Famers that will leave you feeling both energized and centered.

Reserve Your Stay

Sample Itinerary

Group of women standing around talking inside of a small building, carrying drinks.

Friday, September 11

Cocktails and Dinner at Bull Barn | Kick off Cowgirl Fall Roundup with cocktails, a memorable dinner, and an evening of Western hospitality.

Woman on horseback looking towards snow covered mountains.

Saturday, September 12

Breakfast at Trough | Ease into the morning with coffee and breakfast favorites at your own pace.

Morning Activities at Wilderness Outpost | Spend the morning exploring hands-on activities and Western-inspired adventures.

Lunch at Trough | Take a relaxed midday break with fresh dishes and Montana-inspired fare.

Afternoon Activities at Wilderness Outpost | Continue the fun with more opportunities to explore, learn, and embrace the spirit of the West.

Cocktails and Dinner at Chuck Wagon | Gather for cocktails and an inviting dinner in a quintessential Montana setting.

Two women inside an empty arena, getting ready to toss a lasso.

Sunday, September 13

Breakfast at Trough | Start the day with a leisurely breakfast and fresh coffee.

Morning Activities at Wilderness Outpost | Head to the Wilderness Outpost for another morning of adventure and discovery.

Lunch at Trough | Enjoy a relaxed lunch before an afternoon of activities.

Afternoon Activities at Wilderness Outpost | Spend the afternoon making the most of the Roundup with hands-on experiences and Western-inspired fun.

Cocktails and Dinner at Saddle Club | Gather at Saddle Club for cocktails and dinner surrounded by the spirit of Montana’s ranching heritage.

Three women on a blue raft, fly fishing on a river with fall trees behind them.

Monday, September 14

Breakfast at Trough | Enjoy one last breakfast before heading out for the day.

Fly Fishing on the Blackfoot River | Cast a line on the legendary Blackfoot River and experience the beauty of Montana’s waters alongside a Paws Up fly-fishing guide.

What’s Included

Three nights of accommodations
All daily meals, nonalcoholic beverages and a selection of beer, red and white wine and well liquors
Round-trip transportation service to/from Missoula International Airport
All on-property transportation
One trail ride activity and a half day of fly fishing

Group of cowgirls in a row, holding up their arms and cheering on horseback.

September 11-14, 2026

Event Package

Inclusive rates starting at:

$3,445 per person

Call (800) 210-6445

Rate for three nights including tax and resort fee, based on one adult staying in a bedroom suite. Valid with a three-night minimum stay from September 11-14, 2026. Space is limited to the first 60 women who register (18 and older).

National Cowgirl Museum and Hall of Fame

Paws Up Montana believes in the adventure of free-spirited women everywhere, which is why we’ve teamed up with the National Cowgirl Museum and Hall of Fame for our Cowgirl Roundup events. Come ride and dine alongside Cowgirl Hall of Famers, who “exemplify the courage, resilience, and independence that helped shape the American West.

Woman in a redshirt paining outside behind mountains and a forest.

Terri Kelly Moyers | 2015 Cowgirl Honoree

Renowned for her striking Western artwork, Terri Kelly Moyers has built an acclaimed career capturing the spirit of the American West, particularly through her depictions of horses. Her work has been exhibited at the Forbes Building, the Gene Autry Museum, and the National Cowgirl Museum and Hall of Fame, earning prestigious honors including two Frederic Remington Awards and the Prix de West Purchase Award.

Woman holding a camera on a dry plain with a blue cloudy sky behind her.

Laura Wilson | 2019 Cowgirl Honoree

Award-winning photographer Laura Wilson has spent her career documenting the landscapes, traditions, and people of the American West. Her work has appeared in The New York Times Magazine, The New Yorker, Vanity Fair, GQ, and Vogue, and her acclaimed books and exhibitions have earned numerous honors for capturing the enduring spirit of the West.