This post is part of the 100 Days ’til Christmas Challenge — one small step each day to make the holiday season less stressful and a lot more fun.
The holidays are magical, but let’s be honest—holiday entertaining can also be one of the most stressful parts of the season. Between family dinners, class parties, trunk-or-treats, and office potlucks, it doesn’t take long before your calendar feels overwhelmingly packed.
That’s why today’s challenge is all about getting your holiday entertaining plans onto the calendar now—while you still have space and options.
The years I’ve planned early are the years I actually enjoyed myself. I wasn’t running around frantic or double-booking, and I didn’t have to squeeze in a party at the last minute. And trust me, it’s a whole lot easier to set your date now than two weeks before the holiday, when your calendar is already filled with other people’s events. If you block your time early, your party takes priority, and you’ll know when to confidently say “no” to overlapping invitations.
Why You Should Plan Your Holiday Entertaining Now
- Calendars fill up fast. Class parties, trunk-or-treats, and neighborhood events will take over before you know it.
- Your party deserves space. Choosing your date early makes your event a priority instead of an afterthought.
- Stress reduction. Knowing when you’re hosting helps you budget, shop, and prepare without scrambling.
- Peace of mind. You’ll know exactly what you’re committed to, and you can enjoy the holidays without worrying about saying yes to too much.
Decide What Holiday Entertaining You’ll Host (and What You Won’t)
You don’t have to host everything. Pick what feels doable and fun, and let the rest go. Some ideas to consider:
- Halloween parties. One of my personal favorites is hosting a Halloween mystery dinner. It’s such a fun tradition in our family, and I’ll be sharing a printable soon to make planning one easier.
- Thanksgiving dinner. Whether it’s a full spread or a simple potluck, Thanksgiving takes planning.
- Christmas Eve or Christmas Day dinner. These tend to be big events, so claim your date early if you’re hosting.
- Cookie exchanges. A low-key way to gather friends and share holiday treats.
- Game nights or casual get-togethers. Perfect for families or neighbors.
- New Year’s Eve/Day parties. A festive way to wrap up the season.
Remember, it’s about quality over quantity. Hosting one intentional event is better than overcommitting to three and burning yourself out.
Get It on the Calendar
This is the part that makes everything real. Pull out your calendar—whether it’s digital, printed, or hanging on the fridge—and block off your hosting dates.
Take into account:
- Kids’ sports schedules and school parties
- Work or church events
- Travel plans
By setting your party dates now, you’re saving yourself the headache later of trying to squeeze them in. It also keeps you from saying yes to something else only to realize it conflicts with the holiday entertaining event you really wanted to host.
Use the Party Planner Printable
To make holiday entertaining less overwhelming, I put together a free 2-page Party Planner that keeps all your details in one place. Inside you’ll find:
- A guest list with RSVP checkboxes and a space to track how many people are coming
- A food & drink planner with spots for quantity needed, cost, and a purchased checkbox so nothing gets forgotten at the store
- An activities planner with a list for supplies you’ll need
- A party prep & to-do checklist to make sure you stay on track before the big day
It’s simple, practical, and designed to help you enjoy your party instead of stressing over it.
👉 Grab the Party Planner free when you sign up for my newsletter. You’ll get instant access to this printable plus all the other freebies in the 100 Days ’Til Christmas Challenge.
Tips for Smooth Holiday Entertaining
A few little things that make a big difference:
- Start guest lists early. This gives friends and family plenty of time to plan.
- Think about themes or traditions. Adding a personal touch (like a cookie-decorating station or a mystery dinner) makes your party memorable.
- Potluck or solo? Decide whether you’ll do all the cooking or ask guests to contribute.
- Menu plan now. Even just a rough outline helps you shop smarter and snag deals on non-perishables early.
- Create a “party box.” Keep napkins, candles, serving platters, and other essentials in one spot so you’re not scrambling the day of.
Your Challenge for Today
- Decide which holiday entertaining event(s) you’re hosting this season.
- Write them down and block them off on your calendar.
- Grab the Party Planner printable and start filling in details for at least one event.
