Halloween is right around the corner, and for many workplaces, it can feel like just another item on the to-do list. Between deadlines, year-end projects, and trying to balance fun with professionalism, planning a memorable Halloween event might seem like a daunting task.
But it doesn’t have to be that way. Halloween presents a unique opportunity to energize your team, spark creativity, and foster meaningful connections, all while having a little fun. With the right mix of planning and imagination, you can create team-building activities that get employees laughing, collaborating, and enjoying the season together. Here are a few ideas to make your Halloween celebration more than just candy and costumes.
Costume Contests with a Twist
Costume contests are a Halloween classic, but you can elevate the experience by adding a team-building twist. Instead of individual costumes, encourage group or themed outfits that require coordination and creativity. Teams can collaborate to create a story behind their costumes or design a “theme” that spans departments, projects, or even company values.
For example, a team might dress as characters from a popular TV show or recreate a famous movie scene together. To add some friendly competition, assign points for creativity, teamwork, and presentation, turning the contest into a fun challenge that rewards collaboration as much as individual flair.
Beyond the entertainment value, costume contests can reveal hidden talents and encourage employees to step outside their comfort zones. They’re a playful way to break down barriers, spark conversation between colleagues who might not interact daily, and inject energy into the office culture. Even remote teams can participate virtually by submitting costume photos or joining a live video showcase.
Pumpkin Decorating or Carving Challenges
Another classic with endless possibilities, pumpkin decorating can be transformed into an engaging team-building activity. Divide employees into small groups and assign each a pumpkin to decorate or carve, encouraging creativity and collaboration. For added fun, create themed challenges like designing a pumpkin that represents your team’s mission, a seasonal scene, or even a favorite company project.
If carving isn’t ideal for your workspace, painted or decorated pumpkins can work just as well. You might also organize a pumpkin relay challenge, where teams rotate through different stations, painting, accessorizing, or sculpting, adding a collaborative, fast-paced element to the activity.
These pumpkin challenges do more than entertain; they promote teamwork, problem-solving, and creative thinking in a relaxed, festive setting. Participants learn to communicate effectively, divide responsibilities, and share ideas in real time, all while having fun in a low-pressure environment. The best part? At the end of the activity, everyone can admire the results, share laughs, and even vote on their favorite designs, creating a sense of shared achievement.
Halloween Scavenger Hunts

Take team-building up a notch with a Halloween-themed scavenger hunt. Whether it’s inside the office, around your local neighborhood, or even virtually, scavenger hunts combine problem-solving, creativity, and collaboration in a festive, playful way.
Teams can search for hidden spooky items, solve riddles, or complete themed challenges, earning points along the way. For example, employees might locate mini pumpkins hidden around the office, snap photos with Halloween props, or decode cryptic holiday clues. Virtual scavenger hunts can include tasks like taking themed selfies or finding specific objects in their homes, ensuring remote teams can fully participate.
The benefits go beyond fun. Scavenger hunts foster team communication, strategic thinking, and camaraderie, helping employees engage with one another in a dynamic setting. They’re also highly adaptable, making them suitable for small teams, large departments, or even multi-location offices.
Themed Team Games

For a quick, high-energy option, try Halloween-themed team games. Trivia, “Monster Mash” dance-offs, spooky escape room challenges, and virtual mystery or spy games are all great ways to get teams laughing and working together.
Trivia can test knowledge of Halloween traditions, pop culture, or even company history with a holiday twist. Escape room–style challenges whether physical, hybrid, or fully virtual encourage teams to collaborate under pressure, solving puzzles and cracking codes to escape before time runs out. Virtual games like Mystery Mansion, Agent X, and Digital Detective Challenges provide remote employees with an immersive, engaging experience that fosters problem-solving, communication, and camaraderie. Lighter virtual options such as Custom Company Trivia, Guess the Tune, or Logo Mastermind add energy and laughs, keeping everyone involved.

These games are perfect for short bursts of fun during a busy workday or as part of a larger event. They provide the excitement of competition while strengthening team bonds and keeping everyone engaged. Bonus: because many of these activities can be adapted for hybrid or fully remote teams, no one misses out on the Halloween fun even from a distance. Strayboots can help plan and facilitate these games, ensuring your team has a seamless, engaging, and memorable Halloween experience.
Bring Your Team Together This Halloween
Halloween at work is more than just costumes and candy; it’s a chance to energize your team, spark creativity, and strengthen connections. By incorporating fun, interactive activities like costume contests, pumpkin decorating challenges, scavenger hunts, and themed team games (including virtual options), you can create a celebration that’s memorable and engaging for everyone.
The key is to pick activities that match your team’s personality and dynamics, whether your employees are in the office, remote, or a mix of both. These experiences encourage collaboration, laughter, and camaraderie, giving employees a chance to bond in ways that extend beyond their daily tasks.
Ready to make your Halloween celebration unforgettable? With Strayboots, a corporate event planner, your team can enjoy high-energy games, interactive challenges, and festive activities that strengthen collaboration, spark laughter, and create memories that last well beyond the holiday.


