Normally I would open with some cheesy line about ‘retreat season’ or something like that, but considering the abundance of summer, fall, winter, spring, late-spring, early-winter, mid-fall and everything-in-between retreats… it’s always retreat season. I haven’t figured out yet if rather than cramming all of these jokers into a season or year-round retreat schedule carries more pressure, but I’m tempted to say yes.

To be clear, let’s define ‘retreat’ before going further.

I know there are key differences in the various types on youth trips and excursions, typically a retreat carries with it 4 basic characteristics that I’m definitely not making up as I type this:
  • Length: Short term, usually 4 days or less (anything longer is totally camp)
  • Low Tech: Zero to limited available technology, you’re retreating after all
  • Location: Isolated. Rural to Wilderness, just away (again, retreat) the object is to get away and disconnect, that’s difficult (but not impossible) to do in your neighborhood
However, just about any trip will check a few of these boxes, so for our purposes: mission trip = retreat, DNow = retreat, Spring Break Trip = retreat, anything with ‘retreat’ in the title = retreat, etc., etc. The point is, you are having/will have retreats and you want them to go well. So let’s help make that happen.
As with most things, we can break it down and build a good retreat by asking a few questions: Who, what, when, where, why, how—the questions. Making sure your bases are covered will significantly lower your stress level and crank up your chances to create a quality retreat for your students (and adults, and you as well). So let’s ask some questions – also take note that these overlap on a real timeline, with the exception of Question #1 that is.

Question #1


The first question we need to ask is why are we doing this?

Is there a need for a retreat this weekend/season or is it just something that’s ‘always been done’? Neither answer is inherently right or wrong (we won’t get philosophical here, just speaking practically). However, if you’re having a retreat because it’s just what you do that can affect your whole outlook, don’t simply go through the motions. If your group is going on a retreat because it’s a unique opportunity to get away, refresh and reset, connect with the group, get to know the new 6th graders, celebrate the seniors… you get my drift. Depending on your goal, plan to encourage the feeling that you’re going for. If you’re looking for group building, factor in time (and a place) for activities. If it’s all about personal development, create times for reflection and solitude. Either way, it’s never a bad idea to limit (or eliminate) phone/screen time. Make sure it’s something that you can get behind and at least marginally get excited about—because it will show.

Question #2


In all senses of the phrase, when is this retreat?

The time of year you’re throwing down will affect several other aspects of the trip, as will how much lead-time you have to work with. Earlier is better, but there’s a natural threshold for that as well. Don’t start planning a weekend retreat the week before (that’s not a retreat, it’s either a spontaneous event or a debacle), and don’t begin planning your summer 2021 trip during spring 2019 (too much can happen to change details, ideas are fine). I’m not naturally a planner, but discovering that all appropriate locations are booked too late will change anyone’s perspective.
Typically beginning the year’s planning in the fall (including any retreats for the next fall) is a good strategy. For international trips (not retreats, btw), begin at least a year out. I learned to carve out a day or so and get the ‘big rocks’ on the calendar, even booking the locations in order to
  • Actually, put them on calendars to advertise to families, and
  • Give myself and other staff the nice assurance we have somewhere to go.

Once that’s done, I start adding details like themes and speakers/bands (more on that later) about 6 months out and recruiting volunteers around 3 months, working on the details here and there but making sure everything possible is done, DONE, a week out. This leaves time for me to freak out when I inevitably forget something until the last minute. It’s fabulous.

When are we ______?

A month or more out (even more if you’re printing stuff for it or sending out information) work out a schedule for the retreat. Understanding that retreats are retreats, don’t hold too tightly to it, but work out meal times (some locations will be strict with those), worship times, free time, etc and create a rough schedule. This will let you focus on details the last few weeks and make sure you know which groups will be where and when—and allow you to relate as much to parents as you want to reveal, and being able to tell parents what their kids will be doing at all times is never a bad thing. Are you having a party? A bonfire? A scavenger hunt? Work with the host to make sure your timing and their line up. See? You’re already feeling more confident.

Question #3


Are we there yet?

Where are you going, and how does it play into the retreat? Rustic cabins for a real getaway, beach trip for spring break or end of summer, mission trip to Croatia, all of these will have very different settings that will influence the structure of your trip. The available options at the site will affect available activities as well: do they have a zip-line? Sweet, there’s an option. Ropes course, big giant field, pool…you get it. Check out the amenities your location has, ask what makes them unique and play into that. You know your group, look for options they’ll enjoy, and try to avoid somewhere that has options they won’t—many places’ (not all) prices are affected by available options, so you’ll pay for what they have even if you don’t use it.

How far away is it and how are you traveling?

Speaking of, do you have enough transportation if more than you’re planning on sign up? Figure out the accommodations and where your students/adults/leaders will be sleeping (believe it or not some people don’t think about that). How close are the accommodations to each other, to water, to bathrooms, to food—and how does that play with your group? Do they/you allow food in the bunk areas? If not where are you setting up snacks? Where will your group (or groups) have free time, and does your host have/need staff for it? Ok, this was way more than one question, but there are several to ask when it comes to where.

Question #4


This one seems like a no-brainer because obviously ‘who’ is your students, but it could be all of them, middle school only, high school, or even college—each one of these requires a little structure and format tweaking that could have larger effects. Mostly this is about volunteers, leaders, and groups—students are a given. So (if you’re having groups) who will be in each group? I usually try to divide up male/female, middle/high school and separate siblings/BFFs when we have the whole group because I’m mean. Relatedly, I bring parents of students on the trip, but they don’t lead their own children in those groups because I’m nice. Depending on your composition/setup/special needs this may not work for you, and it certainly doesn’t work for all situations—it all depends on what your groups will be doing and talking about—some topics don’t need middle schoolers, and some activities will be served better pitting middle school against high school. Planning this out will save you a massive headache.

Speaking of volunteers, whom are you bringing?

Do you want all parents, all college chaperones, all seasoned veterans (you know, old people) or a mix? Well, that depends on your adults and you, but keep in mind parent groups that are good friends and how those personalities interact… I’ll just say they can be just as bad/good as your students.

Who’s leading this shindig? Who’s rocking the tunes?

If it’s you and you, then just ignore this paragraph. When recruiting speakers/preachers/leaders and musicians, it’s just as easy to knock it out of the park as it is to bomb totally. Just use your own networks and ask folks who have killed it in the past, and of course budget accordingly. I will add one thing: if you have a typical worship band they can be great for some retreats, but giving them an opportunity to take time and enjoy worship on ‘the other side’ can be encouraging and life-giving.

Question #5


What are you doing?

I promise this isn’t as dumb as it sounds. You’re creating a retreat, but what exactly are you doing? Decide what (if any) your theme will be, and break that down into worship sessions and small group (if any) sessions. Communicate your theme with whoever is leading/preaching/teaching because that’s pretty important—music, too—and work with him/her/them as much as y’all are comfortable. More is better, but there’s a not-so-fine line somewhere between micromanaging and chaos.
Back to the schedule, what exactly are you doing and when? This is where you decide how structured you want your retreat to be—which also depends somewhat on the location and what’s available—how much free time you’ll work in, how much ‘mandatory fun time’ or structured activities, bonfires, or what have you. Figure out when small group, Bible study, and/or quiet time fits in. If you’re coordinating free time with the hosts, you may need a sign-up for various activities, and creating that before the retreat will ease a decent amount of stress. Again, there’s no real limit to how specific you can get here, but don’t over think it. Remember: retreat.

Question #6


Lastly, the one most of us don’t want to think about.

How are you making this thing happen?

Big, booming retreats are fantastic, but if we blow entire our budget on just one that makes the rest of the year very disappointing. Before you book anything, compare prices for lodging, food, and transportation to get there—those are the big ones. Some places will save you a chunk by allowing you to provide your own food, but then you have to provide your own food (and cooks). Perhaps not quite surprisingly, how you’re getting all your stuff there is easily overlooked. Packing lists, reminders, and a borrowed scout troop trailer were always my go-to, but the important thing is to bring it with you.


This is a student trip and snacks are a must. How you’ll be snacking is simple, considering you know how those snacks will be arriving. If you have it in your budget you can provide everything, or just supplement and ask each student to bring something—even grades bring sodas, odd grades bring salty snacks, etc. Most of the time a good relationship with the senior citizen ladies will produce quite a few baked goodies that have no rival. Last but not least, how will you rep the trip? By that I mean don’t forget the shirts, those jokers are key to a successful retreat. You know the story with these though, incorporate your theme, find a catchy design and splash it on a Comfort Colors® or whatever the kids are rocking now, and always buy a couple of extras.

One last thing

Scout your trip! 

I didn’t discover the value of this until recently, but scouting a first-time retreat is an invaluable resource for a successful trip. Go, walk through your schedule, check out the digs, the worship/rock out space, ask about the sound and presentation setup, inspect the dining hall and ask about times and menu items. We all know how crazy retreats can be and how unpredictable youth trips are, so walking through and laying eyes on your destination will help you put things together and avoid as much of the unexpected as possible. And, of course, hopefully helping you out when you begin planning your multitudinous retreats in the coming months.