The holiday season can be one of the most exciting times of the year for employees but it can also be one of the most stressful times for companies planning events. Between juggling budgets, balancing team preferences, and trying to keep things fresh year after year, it’s easy to fall into the trap of the same old cookie-cutter holiday party or gift exchange.
The pressure to do something meaningful, creative, and engaging for your team is real. After all, the holidays are a prime opportunity to celebrate your team’s hard work and bring everyone together, but how do you make this year stand out? If you’re feeling the weight of this challenge, you’re not alone. More and more companies are getting creative this season, looking for fresh ways to celebrate that not only offer fun but also foster team bonding and engagement. In this blog, take a look at some of the unique and creative ways companies are celebrating the holidays this year, and how you can do the same.
The Pressure of Planning Holiday Events

Holiday events are a long-standing tradition at many companies, but they often come with a set of challenges. One of the biggest struggles is finding activities that are not only inclusive and budget-friendly but also fun and memorable. Year after year, it’s easy to feel like you’re falling into the same patterns, leaving employees feeling uninspired or disconnected from the experience. And then there’s the pressure to satisfy everyone—after all, holiday events are meant to build morale, show appreciation, and create moments of joy. But how do you meet those goals when employees are so diverse, with different expectations, preferences, and schedules?
Additionally, with remote and hybrid work environments, planning events for teams that aren’t all in the same location has become even trickier. How do you create an event that’s engaging for those who work remotely, without making it feel disconnected or forced?
While it may seem like a daunting task, many companies are rising to the challenge, embracing creativity to make their holiday events truly shine. By thinking outside the box, companies are able to host holiday celebrations that offer fun, foster stronger connections, and truly make employees feel appreciated, no matter where they are.
5 Creative Ideas Companies Are Using to Celebrate the Holidays with Their Teams
Holiday Scavenger Hunts
A holiday scavenger hunt is an exciting and interactive way to engage your team in both an indoor and outdoor setting. Whether you host it virtually or in person, this activity encourages teamwork, problem-solving, and creativity. Teams can work together to solve holiday-themed riddles, complete challenges, or find specific items within a set time frame.
For in-person events, you could organize a scavenger hunt around the office, the city, or even at a local park. For virtual teams, platforms like Strayboots can help create an engaging online scavenger hunt that’s just as interactive and fun. The beauty of this event is its flexibility whether it’s a festive hunt in the office, a city-wide exploration, or a team-based photo challenge, this activity fosters collaboration and laughter, making it a great way to close out the year.
Team Volunteer Activities
Giving back is one of the most meaningful ways to celebrate the holidays while also bringing your team together. Many companies are organizing volunteer activities that help their teams contribute to the community whether it’s assembling care packages, preparing meals at a shelter, or participating in charity drives. Volunteering as a team not only creates a shared sense of purpose, but it also strengthens the bond among employees.
These CSR (Corporate Social Responsibility) events give teams an opportunity to work together toward a goal that transcends the workplace, allowing them to give back to their community while making a positive impact. Not only does this create goodwill, but it also aligns your company’s values with the holiday spirit of giving.
Virtual Holiday Trivia and Game Nights
For remote teams, keeping employees engaged during the holidays can be a challenge. Virtual trivia and game nights are a fantastic way to keep spirits high and provide a little friendly competition. Platforms like Zoom, Microsoft Teams, and Slack can facilitate games that bring employees together for a fun break from work.
You can host holiday-themed trivia where teams compete to answer festive questions, or even try virtual escape rooms or bingo games. This kind of interactive event allows employees to bond, engage in some light-hearted competition, and unwind without the pressure of traditional office parties. It’s a great way to include remote workers in the festivities and bring a sense of unity to the team, no matter where they’re located.
Customized Holiday Workshops
This holiday season, companies are opting for interactive workshops that engage employees in fun and meaningful ways. Whether it’s a DIY holiday craft workshop, a gingerbread house decorating challenge, or a holiday cooking class, these hands-on activities foster creativity and team collaboration.
Customized workshops are perfect for teams who want to learn something new together while enjoying the holiday spirit. Employees can bond over creating something memorable whether it’s a team project or a personal keepsake. These activities are particularly great for fostering a relaxed, informal environment where employees can connect and express themselves creatively, far from the usual deadlines and office pressures.
Seasonal Team Building Challenges
With the holidays being such a unique time of year, it’s the perfect opportunity to bring a seasonal twist to team-building activities. Whether it’s a holiday-themed relay race or a snowball toss competition (indoor, of course!), seasonal challenges offer a fun way for teams to work together while celebrating the time of year.
Incorporating holiday elements into these challenges, like decorating a tree in record time or building the best snowman out of marshmallows, makes the experience more lighthearted while still encouraging important skills like communication, strategy, and creative thinking. These activities add an extra layer of excitement and give employees something to look forward to during a season that often feels rushed.
Why Creativity Works for Holiday Events
When it comes to holiday events, creativity is key. After all, the holiday season is about more than just traditional celebrations; it’s about making memories, connecting with colleagues, and showing appreciation. Creative activities make the holidays feel special by offering employees a break from routine while still aligning with company goals and values.
Creative events also help strengthen company culture. They allow teams to come together in a way that fosters collaboration, boosts morale, and encourages out-of-the-box thinking. In a time when employees are working hard to meet year-end goals, offering fun and engaging activities shows that the company values their well-being and wants to invest in their growth, both professionally and personally.
How to Make Your Holiday Event Creative and Successful
Planning a creative holiday event requires more than just picking an activity off a list. Here’s how to ensure your event is both meaningful and memorable:
- Know your team’s preferences: Tailor your event to what your employees enjoy. Consider their interests and personalities, and choose activities that cater to different groups (remote, introverts, extroverts, etc.).
- Set clear goals: Whether you want to improve team bonding, celebrate achievements, or simply offer a fun break, make sure your event has a clear objective that aligns with your company’s culture.
- Make it inclusive: Ensure that all activities are accessible and enjoyable for everyone, no matter where they’re located or their physical abilities.
- Focus on fun: While the holidays are about appreciating your team, remember to keep the atmosphere relaxed and fun. The goal is to create an environment where everyone can enjoy themselves, reconnect, and recharge.
Make This Holiday Season One Your Team Will Remember
This holiday season, make your company retreat or celebration more than just another cookie-cutter office party. By embracing creativity and thinking outside the box, you can craft an event that fosters teamwork, celebrates your employees’ hard work, and leaves everyone feeling connected and appreciated.
Whether it’s a holiday scavenger hunt, a volunteer activity, or a creative holiday workshop, the key is to engage your team in ways that make them feel valued. Creative events don’t just provide a fun break, they bring your team closer, boost morale, and reinforce company culture.
So, as the holidays approach, take this opportunity to get creative and plan an event that your team won’t forget. Ready to start planning a memorable experience for your team? Contact Strayboots today and plan an engaging, creative holiday celebration that will leave everyone excited for the new year.