Transitioning Into Fall Intentionally

While summer of 2025 doesn't officially end until September 22nd, the leaves have probably started falling in your neighborhood. Your local big box retailer swapped out its back-to-school corner for Halloween costumes. It's pumpkin spice season at Starbucks and Dunkin'. And your Labor Day party capped off another summer of good times in the backyard.

For many families, planning ahead is the secret to a great summer. We don't always apply the same forethought to the fall. But between school, extra curriculars, working teens, your company's big Q4 push, and holidays on the horizon, it's just as important to make some plans now before your autumn blows by.

Use these three steps to bring your family closer together this fall.

1. Create a Family Calendar

Now that the "lazy days of summer" are over, every family member's schedule is probably filling up fast. A family calendar can help keep everyone on the same page.

Even if Mom and Dad's shared digital calendar is the official record keeper, consider adding a big paper calendar to the kitchen so it becomes part of everyone's morning routine. Start by filling in all the have-to's: soccer practice, work, weddings, birthdays. If you already have some fall traditions, pencil them in next.

And when you find a weekend that's blank, box it off for family time.

2. Fill Your Fall Basket

There's still plenty of sun left for a late summer trip to the beach, camping, or waterpark run. But if you want to make fall special, brainstorm some new activities that you'll enjoy bundling up for, such as:

  • Harvest festivals

  • Biking and hiking to enjoy the foliage

  • Apple and pumpkin picking

  • Visiting your alma mater (Tailgating! Football!)

  • Holiday gift shopping (It's never too early!)

If you're looking for indoor adventures, fall might be a great time to visit a city that's a big summer tourist destination. You might have an easier time finding hotel rooms, theater tickets, and dinner reservations.

Fall is also considered the "off season" for many major theme parks and resorts. Cooler weather and more kids back in school means less waiting in line and more thrills. Your favorite park might also offer seasonal attractions around Oktoberfest or Halloween.

But don't give up on fall fun just because your family's calendars don't sync up.  If you don't have enough shared time to hop on a plane, jump in the car for a long weekend road trip and meet your cousins at their town's fall festival.

3. Prioritize

It's likely that once you organize your family's fall calendar, you don't have as many free weekends as you did in the summer. You won't be able to attend every Oktoberfest or home football game. You and your spouse might decide to go apple picking by yourselves. Maybe you have to carve pumpkins over two nights because of your teen's work schedules. Older kids might want to pull a couple activities out of your fall basket for themselves and their friends.

And that's OK. Pick two or three things that everyone is most excited to do and put them on those dates you blocked off for family time. Perhaps one of them will become a new family tradition that you’ll organize your whole fall around next year.

If you do manage to find time for a big family fall trip, consider having a quick meeting with us so that we can review your annual travel budget. As we head into the holiday season and the end of the year it’s important to keep every piece of your Life-Centered Financial Plan in sync so that you can achieve your annual goals and prepare for a successful 2026.