Hit the high notes under the big skies with this special sweepstakes!

Every now and then, something unexpected ​blows in and changes the tempo of everyday life. This time, it’s a shot at winning an unforgettable escape to Montana’s most electric summer event​. Yes, we’re talking wide skies, mountain air​ and three days of music that echoes through the pines. Thanks to the Montucky Big Sky Summer Fly Away Sweepstakes, hosted by none other than E. & J. Gallo Winery, two lucky folks​ and their even luckier ​chosen guest will be packing their bags for a weekend at the 2025 Under The Big Sky Music Festival in Whitefish, Montana. This is not even close to an average trip​…it’s a festival getaway wrapped in comfort, excitement and adventure, valued at a ​surprising $5,000 per ​winner!

​This is a trip where airfare ​is covered, ground transport ​is sorted​, three nights of lodging ​is on the house​ and ​comes wrapped in the most unforgettable summer story. You’ll find yourself in one of the most scenic corners of the country with two tickets to a music festival that’s​ foot-stomping, soul-lifting and crowd​ pleasing. And for all that the value checks in at $5,000​ twice, since two winners will snag it. That’s ​likely a serious upgrade from your usual weekend plans, where craving something fresh on your calendar​ can become a reality!

Not only do you get to​ be entertained under Montana’s endless skies, but you’ll also have the peace of mind of everything being handled​ from airport to hotel and back again. No checklists. No ​stressful planning. Just you, your favorite person and an epic soundtrack ​of tunes rolling through the mountain air ​and under the stars. You’ll be staying in a handpicked hotel that’s all about comfort and cool vibes, perfect for resting your dancing feet at the end of each jam-packed day.

Sweepstakes Details:

  • Grand Prize:
    • A Trip to Whitefish Montana With Tickets to a Music Festival ($5,000)
  • How to Enter: Fill in your required information on the official entry form. Check rules for further details and options for entering.
  • Increase Your Odds of Winning By: Be sure your entry is eligible by following the official rules 
  • Contest End Date: June 15, 2025

Learn More:

If you’re already mentally packed, we get it because who wouldn’t want a free trip like this? This experience will give you that rush of music under the sky, the joy of discovering new artists live and the rare freedom from an anxiety filled itinerary to one that says, “just have fun.” Whether you’re in it for the headliners or the hidden gems, this festival promises memory-making moments that deserve their own album. E. & J. Gallo Winery has stepped in with this ultimate giveaway. Known for crafting everything from refreshing sips to crowd-pleasing vintages, they’ve teamed up with Montucky to give your summer some serious altitude and new heights in entertainment. It’s a pairing as perfect as an ice cold drink on a hot day because what better way to enjoy summer than with great music and a delightful trip?

Enter to Win:

The Montucky Big Sky Summer Fly Away Sweepstakes will have its winner stepping into a real-life playlist where the backdrop is snow-dusted peaks and the relaxation comes from losing yourself in the rhythm. So, here we have two prizes and two winners with two unforgettable journeys valued at $5,000 each. All you have to do is throw your name in the digital hat for a chance to be one of the chosen few heading to Whitefish, Montana in July 2025. Whether you’re entering as a festival newcomer or a seasoned music lover, the Montucky Big Sky Summer Fly Away Sweepstakes makes it easy to dream a little louder this summer. Picture yourself soaking in songs from your favorite artists, taking in views that belong on a postcard and creating stories you’ll be telling long after the music stops. Click here for your chance to get away and see the beauty Montana is waiting to share! Next, continue your search for some of the best prizes out there through our website!

Pam’s Perspective

So here’s your friendly nudge to push on and resist scrolling past this one. Enter now and get your shot at a Montana getaway that’s got all the right notes for a perfect escape. After all, when adventure comes calling, the only right move is to answer with an entry and a packed suitcase. Two winners. Three days. One epic festival weekend. Jump in now for a prize that’s in tune for creating an amazing summer!