Ashley Wineland’s Top 10 Essential Touring Hacks Every Independent Artist Should Know

Rolling up her sleeves and putting the work in comes naturally for Ashley Wineland. The country singer-songwriter has enjoyed a breakthrough year thanks to hit singles like “Tumbleweed” and her 2025 “Moments in Time” tour. In her time as a touring and recording artist, Wineland has developed quite a following. Her fans have become known as the “Winelanders,” implying the special relationship she has with her audience. Part of what makes Wineland so appealing is her electric stage presence and immersive storytelling nature. And she’s done it all as an independent artist, just relying on that down south work ethic she was brought up to have. She even acts as her own booking agent, taking the reins in any way that she can.

Wineland’s brand of country is a bit different. She comes from Arizona, which isn’t always as well-connected with country music as states like Texas and Tennessee are. Arizona country music culture has a certain kind of charm, and that’s apparent in her music. It may come as a surprise to some, but Arizona has a very deep “cowboy culture” with its many ranchers and farmers. That culture and the history behind it have influenced who Wineland is as a songwriter. She is a total natural at this, which is reflected in the comparisons she has drawn, like Carrie Underwood, Miranda Lambert, and Gretchen Wilson.

Hot off the success of the “Moments in Time,” Wineland joins us to share her Top 10 “Essential Touring Hacks Every Independent Artist Should Know.” If you are an aspiring musician, we suggest you take good notes.

1. Rewards Programs

“I love a good rewards program. Whether that’s a credit card system for an airline, or the drink rewards programs at fueling stations like Love’s Travel Stops, collect those points and save! You are going to be spending the money regardless, so you might as well rack up your rewards to save your future self some funding.”

2. Pack a Motley of Tools

“If you are travelling in a vehicle of any kind, please ensure you have a comprehensive set of tools. It is inevitable when you are touring that something will break. Usually, it’s the vehicle due to all the stress from the road, but it can be anything. Heck, I’ve used a grinder saw to take locks off our trailer because our keys went missing down a storm drain. You never know when you will need a screwdriver, fix-a-flat, or some good old-fashioned super glue and duct tape. Have it all and always be ready. The band helped repair an awning that unfurled because the wind was so strong.”

3. Shared Calendar

“If you are the leader of your band, you will be asked by everyone 100 times a day what the schedule is, where events are, what the plan for the next day is, etc. Save yourself the same speech having to be recited over and over by creating a mutual calendar and notes for the group. For my team, we have a whiteboard and calendar on our bus fridge with any info the group may need to know. You can also do this digitally if that’s better for your team.”

4. Set Budgets

“While many of us don’t enjoy math, it is vital to a tour being financially successful. Keep accountability for yourself by working in your spreadsheets all of the funding the band is making with base pay and merchandise, and then document your expenses. QuickBooks is a great digital resource to track receipts and expenses as well as manage your payroll.”

5. Pack As Light as Possible

“This goes for fly-ins or driving. You are going to be hopping from hotel to hotel, venue to venue. The last thing you want is to have to manage a bunch of heavy bags on top of your responsibilities. If you can do laundry, do it! Anything to keep your essentials on you and limit the amount of space you need to take up with your personal possessions. Take my advice because I don’t listen to myself and regret it.”

6. Always Advance Your Show

“It’s show business, baby, things are bound to change. Advancing the show means getting in contact with your event coordinator and making sure both you and they are on the same page with all the details. Confirm load in time, parking situation, set length, and verify payment. So many details can be lost in emails or change before showtime. Advancing the show two to three days before the performance allows you to have enough time to prepare and communicate to your team what the situation will be on show day.”

7. Hold Rehearsals

“Rehearsals on the road are awesome! Many are of the mind that touring is the time when rehearsal is over. I argue otherwise. If you are not rehearsing in some capacity on tour, you are not taking what you are learning during the shows and using your downtime to make the show better. Travelling rehearsals can help add that special polish to a show. Grab an acoustic and make it happen!”

8. Find a Travel-Friendly Hobby

“If you’re not actively driving, travelling can become boring very quickly. I always encourage everyone to find a travel-friendly hobby. You spend more time travelling than you do playing on tour. My personal favourites include knitting and reading. Find a good time buster and have fun!”

9. Know Your Go-To Lodging

“You know the areas you are travelling to, find the common place lodging that you love to stay at in all those areas. Maybe you have a specific hotel chain you’ve come to love; make note of that! For my band, when we are not in hotels, we take our bus to Kampgrounds of America (a.k.a KOAs) and we hook the bus up and camp. Between the outdoors and all the amenities, it’s a no-brainer stay for us on the road. Find the places you love and stick with them (especially for reward points)!”

10. Have Backups for Everything

“This plays off of the same energy as point number two. Things break, shampoo bottles leak, instrument cables die, and at some point, you’ll find yourself out of a product with no nearby store to buy it from. If you have the storage, make sure you have back-ups of your essentials for personal and work use.”