Summer is the season of big gestures and big expectations. It’s no wonder it’s known as wedding season. Everyone piles all of their hopes and dreams and expectations (not to mention a large chunk of their savings) into one week (or less!) to count for the entire year and lose their mind if everything isn’t perfect. Or if everyone isn’t grateful the entire time. No pressure.
Spoilers – things are rarely perfect even when you are on vacation.
Like Dr. Ian Malcolm famously said, “life finds a way.”
Whether you had a big family vacation this year or not, chances are you are left now wondering what you will do next year. First, don’t worry too much (some is ok, but not too much) if the kids didn’t seem to love every minute of the trip, or you found yourself bickering with your spouse like home followed you all the way to wherever you were. Or if you didn’t go anywhere all summer, that’s sadly not that uncommon. That was us this year and last year. Sometimes you don’t have the budget for a big trip, or you just can’t get the time off work. Sometimes a lot of day outings to somewhere closer have to suffice.
Two things can be true at the same time – vacations are not a cure-all for stress, and people who are most comfortable with each other are usually the most honest with each other, even if it means hurtful things are said occasionally. But a third thing can be true as well – people who are most comfortable around each other tend to care the most about those people, even if they are not the best at showing it on the regular.
It’s tough to remember in the moment (scratch that, it’s nearly impossible), but my wife and I try our best to remind each other when the kids are being short with us that for every “I hate you!” that “I love you” can’t be too far behind. Sure, it’s easy to push each other’s buttons when you are in close quarters with the same folks all the time, but those are usually the people you also have the strongest bonds with.
If you had a perfect trip this summer, that’s awesome! And even if you didn’t, I’m sure you made plenty of good memories to offset any tough times on the trip, whether it was a long trip or just for the day.
We recently took a trip to the coast, and the kids spent a fair amount of time whining or asking to go home, which made it tough to justify spending the night there knowing what was waiting in the morning and thinking of money going toward outings they may not actually enjoy. But some fun family time in the sand and in the water are the memories I will remember years from now, not that I ruined their far too short little lives when I got them the “wrong” chicken (there’s no parenting handbook that accurately prepares you for that), or that they wanted to go home the first night of a three-night trip. Or that the park by the rental house had the wrong color slide (they wanted blue; this one was green- win some, lose some). We took a similar trip in the fall to a similar location with similar activities, and it seemed like nothing could go wrong. Like any experience, some people will be in the right frame of mind and sometimes they won’t. It is what it is.
Some days are just tougher than others no matter where you are. And you know what? Both trips were really good; one just went smoother than the other. But I bet if I think about them as their own thing and don’t pit them against each other, I’d see both as great. That’s the challenge with taking time off work and planning a trip for your family – you don’t just want things to go well; you need them to go well. And it’s really tough not to have a negative reaction when the people you care about most don’t seem to care how much thought went into making them happy. And it’s also a lot of pressure on them to like something; I have to remind myself of that whenever things get a little too tense on vacation. Not every piece of spaghetti sticks to the wall.
As parents, we never know what memories we try to give our kids will stick; we know they will probably have an easier time remembering anything negative (and parents have the same struggle), but we typically don’t photograph or scrapbook those memories. The good ones where everyone is grinning until their cheeks hurt? Those always make the keeper album. But they aren’t as easy to come by. Sometimes the picture of everyone looking in opposite directions and two people have their eyes closed are the best ones you get, and if you aren’t looking at it through the right lens, you might miss all the smiles that are definitely there.
Just because summer is ending doesn’t mean the memory-making machine has to shut down for the season. School is just around the corner (this week for some, next week for most, and the week of Labor Day for some districts), and that arrives with the inevitable comparison to how the kids looked this time in 2025, but it also means Saturdays are more important than ever. It’s so easy to tell yourself you don’t have the time for a day trip, but it seems like we all get into a groove of surviving weekends in the fall instead of experiencing them. Saturday or Sunday game-day gatherings with friends and family can absolutely count as an experience. Still, they tend to all blend unless there’s a special occasion with someone in town who normally would not be. Some kids love watching the big game with the grown folks, but a lot of kids get bored. Not everyone is going to love every outing, but if you know for sure that one of your club members isn’t going to like the choice out of the gate, it’s probably best to pick something else. Is someone allergic to bee stings? You wouldn’t visit a local farm with the sole intention of seeing where the honey comes from. Think of every outing like that, and you’ll be fine. If there are other things that person can enjoy, then great, but if the whole focus is on something they hate or something unsafe for them to be around, that idea needs to go right in the bin.
Make sure to set up some day trips or at least meaningful outings for the next couple of weekends. Don’t let sports (whether on TV or kids’ games and practices in person) take over the schedule quite yet. Youth sports and college as well as pro football dominate the fall and early winter calendar in many households, but a lasting memory for your little club (while they are still your club) is not against the rules. There are no “can’t miss” games this early in the season, but there are always can’t miss family moments; we just don’t always see them that way until they are in the past and out of our reach. My wife and I keep saying the kids are in our club now, but sooner than we would like to admit, we will be in theirs; before too long, that club will likely dissolve once they have their own kids, and then we will try to join that club. Blockbuster Video tried to prepare us for this in its own way, then went away and turned into Netflix.
Keep the memory-making machine on standby, and plan something fun for your family. Pick fruit on a local farm, check out the newest movie even if it’s one you can’t see yourself watching as long as the kids will enjoy it. I can’t tell you how much I don’t ever want to watch a certain cartoon ever again, but I would be lying to you if I said I don’t find myself humming the theme at random times of the day, and the way our kids’ faces light up when they watch it, I can’t say no.
Limit venue choices so one of the kids can’t pick something the others might hate, but maybe let the kids rotate choosing the outing destination. Or, if you have room to do multiple things in the same day, maybe everyone gets to pick part of it. Or if one gets to pick the outing, maybe another gets to pick where you get lunch or dinner. Sure, it could go badly, but it also could go great. You know your family better than anyone; find something they can all enjoy together. The beach isn’t that far; the mountain isn’t that far; those are easy ways to find something for everyone. Every town has an arcade with games to win tickets; even the least competitive people can have fun with that. Challenge everyone to win the most tickets. What that person wins with the tickets is up to you. Maybe they can buy their way out of a specific chore, or they can pick where you go to dinner.
A lot of people seem to see the coming changes to the season as an excuse to stay indoors or limit outings, but as long as you prepare for the weather, you can still get out and make memories. A lot of local farms start opening their pumpkin patches in the coming weeks, and those usually have some fun activities even if you’re not looking for a seasonal squash. And if you are looking for pumpkins, even better. And if someone in your club has decided a certain team has to be on TV at home, and they can’t miss it? Fine, schedule an outing around that; the game will start and end at specific times, so even if it really is a can’t-miss game for some reason, it doesn’t need to dictate the entire day.
While the kids are still in your club, making memories should be the priority every weekend where possible. One day they will have their own clubs, and the memories they look back on will shape what kind of club they want for their kids. Those may be being created this very weekend; you never know. Will it be a great memory, an ok one, or a forgotten one? Or the most awkward kind – the one they think about as the experience they don’t want to give their kids. We all have our short list of those kinds of memories.
The good news is you really can’t know what memory you will give them, but you can give them the best chance at a good one.
Casey Mabbott is a husband and parent first, and also an experienced and dedicated writer and researcher. Born and raised in the Portland area, when Casey is not spending time with his family gallivanting around Portland and the surrounding areas, he genuinely enjoys helping people (especially families) find the “hidden gems” in the Pacific Northwest. In today’s world of lightning fast information at our fingertips, it’s truly a wonder to stumble across a place, an experience, or an activity you’ve never heard of.