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National Plan for Vacation Day: Tips for Your Montana's Trailhead Itinerary
January 29, 2024

National Plan for Vacation Day (NPVD) began in 2017 and was organized by the U.S. Travel Association. Although they’ve sunset their direct organization of this day, the reason they started this initiative is just as important today as it was then: the American workforce leaves a shocking amount of vacation days unused each year.
NPVD is important to the tourism industry and American workers, alike. The importance of the day is simple: you’re more likely to use your vacation days if you make a plan to do so!
With that in mind, the Visit Billings team wanted to share some tips for those of you planning a trip to Montana’s Trailhead. Whether you’re looking forward to a winter excursion or a summer roadtrip, read ahead for a few trip-planning takeaways!
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No Matter What Time of Year You Plan to Visit, Pack for Every Season! 
“If you don’t like the weather, wait twenty minutes.” We’ve heard that more than we’d like to admit. But there’s an air of truth to it. It applies to Billings (and Montana in general), but even if you happen to visit during a week of consistent sunshine, it’s smart to pack for a variety of weather or activities.
During the summer, one of the most popular road trips in our area will take you through the Beartooth Pass. This scenic mountain pass provides jaw-dropping views of the Beartooth Mountains and is accessible from Memorial Day to Labor Day each year. But even in the heat of July, mountains are mountains! Pack for some chillier weather among the peaks. 
Plan for Extra Time
“I didn’t realize Billings had ______.” This is a common sentiment we hear from plenty of visitors, with a variety of activities, locations, or attractions used to fill in the blank. Whether they’re remarking on our dining options, art scene, or a hidden gem found in the city, it’s not uncommon to stumble upon something you didn’t plan for in your vacation itinerary.
So, make sure you plan time for organic moments of discovery. Your favorite memories from vacation may be made during time you didn’t account for – so give yourself some itinerary wiggle room!
Make Time to Dine Somewhere New
Our team loves sharing restaurant recommendations, and luckily for us, visitors appreciate learning these dining details! No matter why you’ve landed in Billings, whether that’s for outdoor recreation, business travel, or to experience our food scene in and of itself, you’re likely going to make time for a few meals. James Beard Award nominees, mouthwatering brunch spots, and steakhouses that will bring a tear to a cowboy’s eye all call Billings home.
Billings has one of the most vibrant restaurant scenes in the state. For a list of local restaurants organized by neighborhood check out pages 24-26 in our visitor guide.  
Plan for Small Bites, Too
While visiting Billings, we always recommend setting aside one night (at least!) for an experience at one of our local restaurants. Is there anything better than sitting down for a drink, appetizers, a new entrée, and hours of conversation? Unfortunately, not every meal can look like this!  
Sometimes you need a quick bite. Fortunately, small bites don’t need to be mediocre! Whether it’s a pit stop breakfast or lunch on the go, our restaurant scene provides local options for these moments, so you can still indulge in a local, memorable bite while you’re rushing to horseback riding or whatever you’ve planned for you and the fam. Our Foodies’ page is a great resource!
Make a Point to Explore Downtown Billings
Downtown Billings features a bit of everything, so even if you’ve devoted a weekend to mountain biking throughout our region, plan time to explore Montana’s largest downtown! During the day, visit the coffee shops, local businesses, and museums. In the evening, a show or concert at a local theater pairs well with unwinding at a local brewery.
Speaking of…
Enjoy the Billings Brew Trail
The Billings’ brewery scene is something you won’t find anywhere else in Montana. While many communities have fantastic breweries, the options, ease of access, and hop-loving culture in Billings makes for unforgettable experience. Sipping on locally crafted beer, spirits, and wine is a great way to rest and recoup.
Learn more about all of Billings’ craft beverage locations here!
Enjoy the Actual Trails
We can’t recommend something like the Billings Brew Trail without mentioning our actual trail system! If you’re in search of an easy-going trek or an option on steeper sandstone, you’ll have options in-town, just outside the city, or a short drive away. Additionally, Skyline Trail, stretching across was just completed. If you’re looking for some of the city’s best views, you can’t miss this new addition.
Our friends at Billings TrailNet have some great resources! 
Don't Miss a Sunrise or Sunset
Plan for simple pleasures during your time in Montana’s Trailhead, too. Our forever views are even better during early-morning rays or evening twilight. Regardless of your choice in timing, starting or ending your day this way is an incredibly relaxing way step back from the hustle and bustle of your vacation. And if your vacation’s theme is already relaxation… well, that’s a win-win.

visitor guide