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Navigating the Holidays as a Co-Parent: Halloween to Thanksgiving in Maryland

By Christopher Castellano

Insights Couple Walking Child

The holiday season is just around the corner, and for many separated or divorced parents, that means excitement mixed with a bit of anxiety. With Halloween only a day away and Thanksgiving coming quickly after, this is the time of year when custody schedules, communication challenges, and emotional stress can easily collide.

As a Maryland family law attorney, I often see holiday disputes arise not out of bad intentions but from last-minute confusion or lack of planning. The good news is that a little foresight and flexibility can go a long way in keeping the holidays enjoyable for everyone, especially your children.

Start with Halloween: The First Test of the Season

Halloween tends to sneak up fast, and because it’s not always specifically addressed in custody orders, parents often don’t realize there’s a potential for conflict until it’s too late. Who takes the child trick-or-treating? Who attends a school event? What if both parents live in the same neighborhood?

Here are a few tips to get ahead of those issues now:

  • Check your custody order to see if Halloween is mentioned as a holiday. If not, the regular weekday schedule usually applies.
  • Communicate with the other in advance of the day to discuss plans, including where trick-or-treating will take place, who will handle costumes, and whether both parents will participate.
  • Be flexible if possible. If the children want both parents involved, try to make it work.
  • Sometimes alternating years or splitting the evening (one parent for early events, one for later) helps everyone enjoy the night.
  • Put any agreements in writing (a short email is fine) to avoid confusion later.

Even if things don’t go perfectly, remember that kids are focused on fun and memories, not logistics. Keeping a positive attitude and making the evening about Halloween as opposed to parental conflict is key.

Thanksgiving: Plan Now, Avoid Stress Later

Thanksgiving is traditionally one of the major holidays addressed in Maryland custody orders, but problems still arise when parents assume instead of confirming. Whether your order calls for the holiday to alternate based on years or that a mixture of the holiday and the weekend alternates, make sure you’re clear on what the arrangement is.

Here’s how to stay ahead:

  • Like Halloween, confirm the schedule early. Waiting until Thanksgiving morning to coordinate pickup and drop-off times opens you up to conflict.
  • If you are traveling, discuss travel plans now. If your plans include out-of-state travel, your agreement likely has an itinerary disclosure requirement that includes a disclosure timing clause. Make sure you are complying with the terms of your agreement.
  • Flexibility. While it is important to respect your agreement or the order, Courts appreciate it when parents cooperate and show flexibility, particularly in the context of holidays. If one parent’s extended family is unexpectedly gathering that weekend, consider swapping time if it benefits the child.
  • Avoid putting kids in the middle. Don’t ask them to choose where they want to spend the holiday. Present a united front that reassures them both parents are happy they’ll have a good holiday.

If disagreements arise and can’t be resolved, don’t take matters into your own hands. In Maryland, violating a custody order, even for something as well-intentioned as keeping the child for an extra dinner, can have serious consequences. If your order or agreement is unclear or outdated, talk to a family law attorney before acting. Sometimes a simple modification or clarification can prevent larger problems later.

Looking Ahead: Building Better Traditions

While holidays can be stressful, they’re also opportunities to build new traditions. If you’re newly separated or still adjusting to co-parenting, keep your focus on what the children will remember, not custody logistics. Some parents find success by creating new traditions in each household, keeping consistent communication with the other parent about upcoming holidays through shared calendars or apps, and avoiding last-minute changes unless absolutely necessary.

However, holidays are also a time for understanding, and that includes flexibility. That does not mean you have to ignore your order or agreement or let the other parent dictate your holidays, but a bit of flexibility and understanding goes a long way. Your behavior now sets the tone for future cooperation, and Maryland courts consistently encourage co-parents to demonstrate flexibility and reasonableness, especially during the holidays. Showing that you can communicate effectively and put the child’s needs first not only benefits your family dynamic but can also reflect positively in future court proceedings if modifications or disputes arise.

A Final Word

The holidays don’t have to be a source of conflict. By planning early, communicating clearly, and keeping your child’s happiness front and center, you can make Halloween, Thanksgiving, and the rest of the season peaceful and memorable. If you have questions about your custody order, need help clarifying a holiday schedule, or find yourself in a dispute, reach out to discuss as soon as possible. Timely legal guidance can prevent unnecessary stress and allow you to focus on what really matters this season, making lasting memories with your children.

About The Author

Christopher Castellano

“One of the most important roles I serve is as my client’s risk manager. This means identifying the risks inherent in their cases and determining how best to mitigate those risks, while being realistic about potential outcomes.”

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