On a recent search for holiday dates, I stumbled upon National Procrastination Week. This annual event occurs sometime in the first two weeks of March, I guess whenever you get around to it?

It got me thinking how procrastination impacts vacation planning, or more specifically, how procrastinators can still plan an epic Bend vacation. There are times it pays to put things off, and times you really, really should get a jump on things. Knowing which is which can be key.

Pull up a chair (maybe later), gather your trip planning gumption (it’s gotta be here somewhere) and prepare to shine in spite of (maybe because of?) your urge to procrastinate vacation plans just a teensy-tiny bit.

When it pays to NOT procrastinate

As an avid globetrotter who’s been burned more than once by waiting too long, allow me to share some trip-planning wisdom.

If you really, really, really have your heart set on a certain Bend hotel, activity, or Bend restaurant, book early. Full stop, do not pass go, do not perform the silly dance I often regret where I tell myself, “the price will go down,” and I end up paying double or missing some great adventure because I waited too long.

In other words, don’t be me.

This holds especially true for unique adventures like moonlight canoe tours, whitewater rafting, snowshoeing adventures, family mountain biking trips, or the Paulina Plunge, which have limited, seasonal availability and can only accommodate a certain number of folks.

Bend concerts are another prime example. Right now, Hayden Homes Amphitheater is announcing gobs of summer shows. Popular concerts sell out fast, so if you dream of seeing a specific musical act, make sure you’re signed up for concert announcement emails and pounce on presales fast. That simple act can make the difference between “woohoo!” and “boohoo!”

It’s even more crucial for events like the FairWell Festival, which had its Central Oregon debut last year. This three-day music fest was one of my favorite highlights of last summer, and you know what? I almost missed it because I failed to jump on presale tickets, then balked at paying full price. Lucky for me, I scored full-event passes and had the BEST. TIME. EVER.

Learn from my mistake and bookmark your calendar for the FairWell Festival July 19-21. Then visit their website before Feb. 29 to get signed up for a presale passcode. That’ll arrive in your inbox by 9 a.m. on Feb. 29 and the presale starts that day at 10 a.m. Watch the clock, since the public on-sale starts two hours later, and I guarantee hot tickets like Friday general admission (Jason Isbell, Billy Strings, Katie Pruitt, woot!) and Sunday night (Kacey freakin’ Musgraves!) not to mention camping passes (expanded this year!) will go FAST. Check out the whole lineup here.

Last but not least, a word on outdoor adventure. If you’re not familiar with the Central Cascades Wilderness Permit System, the gist is that certain areas are at risk of being loved to death. To mitigate our impact on these precious natural resources, certain areas require permits for hiking and backcountry camping from mid-June through mid-October. This article breaks down the details, but basically, about 40% of overnight permits get rolled out April 2, 2024 for non-procrastinators. Missed the boat? Once permit season starts in mid-June, the remaining 60% of overnight permits get released on a rolling seven-day basis. 

Day use permits are kinder to procrastinators, with 40% released 10 days prior and the remaining 60% released two days prior. Again, I urge you to read the article, particularly the part with examples based on specific dates. It’s not as confusing as it sounds, and I promise this simple act of planning ahead can make a world of difference.

Go ahead and put it off

As every good procrastinator knows, there are times when waiting pays off.

Here’s another example from the live music world (can you tell it’s an obsession of mine?!) Each year, I make a list of Hayden Homes concerts I absolutely, positively must see, no matter what. I watch for those presales and pounce on those bad boys like a rabid cougar chasing down a limping deer.

But then there are shows where I’m like….meh. I’d like to go, maybe, but I won’t be bummed if I miss out. With those shows, I roll the dice on the odds they’ll be included in the Live Nation $20 ticket sale taking place around the start of May. I should note this strategy works only when you’re willing to risk missing out altogether. There’s no guarantee the show you want will be included in the sale, or that tickets won’t sell out long before May. Heck, there’s not even a guarantee the sale will happen. But it’s an option that works when you don’t really care if you get the tickets or not.

I operate the same way with campsites. You know that game many folks play where they study the calendar and jump on recreation.gov at 6:59 a.m. to fight for camping reservations exactly six months before a hoped-for camping trip? 

I hate that game.

But it’s a necessary evil when you set your sights on a specific campground on specific dates. My solution? Be open to anything. 

If I check my favorite campgrounds right now for available sites in mid-July, they’re all reserved. But if I wait and search recreation.gov just a few days before I want to camp, voila! At least a handful of folks will back out of their camping plans at the last minute. As long as I don’t care exactly where I camp, and I’m willing to wiggle on dates, I’ve never not found something.

This system holds true for Bend hotels, though it’s a bit riskier. Prices spike in high season, and folks don’t tend to cancel hotel stays with quite the same frequency as campsites. Still, you might get lucky, especially for wildfire season travel (August and September) when the risk of poor air quality scares off some of your fellow travelers.

Another arena where flexibility pairs well with procrastination? Restaurant reservations. It’s true some of Bend’s most in-demand dining spots have reservation calendars booked months or even a year in advance. But it never hurts to ask about waiting lists. It also helps if you’re willing to take odd hours (say 4 p.m. for late lunch/early dinner, or an extra-late dinner slot at 8:30). And if you call and get a “sorry, we’re full,” please be kind. Bend restaurants face staffing shortages just like everywhere else, and no good comes from berating folks just doing their jobs. 

Ooops, I procrastinated spring break. Now what?

Since we’re less than a month from Oregon spring break, I’d be remiss if I didn’t point out that it’s officially “last-minute.” If you don’t have reservations for spring break in Bend, don’t panic! 

But do finish reading this post and immediately hop online to:

• Read up on why you should spend spring break in Bend. Here’s a blog post to help. Still not convinced? Read this post, too!
• Check for last-minute hotel reservations. Families’ plans change, so you may get lucky and swoop in on someone’s cancellation. Rumor even has it that a handful of Bend lodging spots aren’t fully booked yet. Go find them!
• Search for midweek hotel nights or vacation rentals. Weekends book quickest, even over spring break. If you can be flexible with a Tuesday through Thursday trip, you may have better luck.
• Plan ahead for summer. If spring break this year is just too much, why not take ten minutes to nail down your summer plans? Nab a Bend hotel room and book a family tour or two. Future you will be thrilled (not to mention relieved to avoid the last-second scramble), and you won’t risk missing out.

Happy planning (or not) my fellow procrastinators! I’m wishing you the very best in all your Bend adventures.