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Experience Milwaukee’s holiday cheer with Holly Jolly Hunt, a smartphone-based scavenger hunt perfect for families and friends seeking festive fun.
This holiday season, if you’re looking for a fun, light-hearted way to explore Milwaukee and get into the Christmas mood, the Holly Jolly Hunt offers a cheerful twist on sightseeing. Promising a playful mix of traditional and non-traditional holiday items, this app-based scavenger hunt invites groups of friends or family to uncover holiday-themed surprises around the city. It’s an engaging activity that combines sightseeing, laughter, and a bit of friendly competition—all in one hour of holiday magic.
What makes this experience stand out are a few key features: First, it’s affordable at just $20 per group, making it accessible for families, friends, or co-workers. Second, it’s flexible—you can play it anytime between late November and New Year’s Eve, choosing your own route and pace. However, it’s worth noting that you’ll need a smartphone and the ability to navigate around Milwaukee, which might be a consideration for those without mobile access or limited mobility.
This scavenger hunt is perfect for travelers craving a unique, interactive way to experience Milwaukee’s holiday ambiance, especially those who enjoy a bit of friendly competition or quirky challenges. Whether you’re visiting Milwaukee for a weekend or a local looking for a new holiday tradition, Holly Jolly Hunt offers an accessible, memorable activity that celebrates the season in a lighthearted way.


The Holly Jolly Hunt in Milwaukee offers a different kind of holiday activity—one that’s not only about the destination but also about the journey and the laughs along the way. Playing for about an hour, this activity is designed to fit into a busy holiday schedule, whether you’re looking for a quick family outing or a fun team-building exercise during a holiday gathering.
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Booking is straightforward; you select a date within the specified holiday window (generally from late November through December 31). The activity is booked 13 days in advance on average, which is handy for planning your holiday trip. The cost is $20 per group, accommodating up to 10 participants, making it an excellent value for small groups or families.
The experience includes a mobile ticket and an hour-long adventure. Once booked, you’ll receive a confirmation and instructions on how to access the app, which is your guide for the hunt. The activity is private, meaning only your group plays, and you’ll have a remote guide via text message, offering support if needed.
The hunt begins at Cathedral Square Park (520 E Wells St)—a lively spot right in Milwaukee’s downtown. The route is flexible, and at the end of the hunt, you’ll return to the same meeting point. The starting location offers easy access via public transportation, making it convenient for travelers not renting a car.
Once you start, you’ll be prompted to find and photograph various holiday items—both traditional, like ornaments, Christmas trees, and Santa hats, and non-traditional, such as quirky holiday signs or unique decorations. The app awards points for each item captured, encouraging friendly competition.
But it’s not just about hunting. The game incorporates silly holiday-themed tasks, such as performing a funny dance or singing a holiday song. These challenges are designed to generate laughter and light-hearted moments, making the experience more than just a scavenger hunt.
The game is played at your own pace, which is helpful if you want to linger at certain spots or take a break. As you go, you’ll see your score on the leaderboard—adding a playful competitive element. If you’re traveling with kids, they’ll love the interactive nature and silly tasks, making it suitable for all ages.
Given the cost of only $20 per group, it offers substantial entertainment for the price. The inclusion of all fees and taxes means no surprise expenses, and the one-hour duration is ideal for fitting into a busy holiday schedule.
Although there are no official reviews yet, the activity’s details suggest a broad appeal. The concept of a holiday scavenger hunt is inherently fun, especially with the added element of silly challenges. The fact that it can be played in any city makes it versatile—if you’re a traveler relocating or visiting different places, Holly Jolly Hunt could be a portable holiday tradition.
You’ll need a smartphone to participate, which is the main requirement. It also helps to be comfortable walking around Milwaukee’s downtown area, as the hunt involves searching for items scattered around city streets. The activity is most suitable for travelers who enjoy interactive experiences rather than passive sightseeing.
This activity is perfect for families, groups of friends, or co-workers wanting to share some cheerful holiday moments. It’s especially ideal for those who enjoy small-group adventures and are looking for an affordable activity that combines sightseeing with playful challenges. If you’re visiting Milwaukee during the holiday season and want something more memorable than just wandering through decorated streets, this scavenger hunt offers a fun, engaging way to explore.
It’s less suited for travelers seeking extensive historical or cultural insights, as the focus is on holiday-themed fun rather than education. Also, those without smartphones or mobility challenges might find it less accessible—but for most, it’s a cheerful, light-hearted experience.

The Holly Jolly Hunt in Milwaukee offers a delightful way to celebrate the season. It’s a cost-effective, interactive activity that turns city streets into a playground of holiday surprises. The combination of scavenger hunting, silly challenges, and friendly competition makes it a memorable experience, perfect for families, friends, or even holiday office parties.
For those who appreciate a casual, fun approach to holiday sightseeing, this activity delivers plenty of smiles and laughter—plus a chance to see Milwaukee’s downtown in a festive new light. It’s a great choice for travelers seeking authentic, playful holiday entertainment without breaking the bank.
If you’re looking for an activity that emphasizes fun, connection, and holiday cheer, Holly Jolly Hunt is well worth considering. It’s a simple, joyful way to make your holiday trip a little more special.

Can I cancel my Holly Jolly Hunt reservation?
Yes, you can cancel free of charge up to 24 hours before the scheduled start time for a full refund.
Is this activity suitable for children?
Yes, it’s designed to be inclusive and fun for all age groups, with silly challenges and holiday items that appeal to kids and adults alike.
Do I need to bring my own smartphone?
You will need a smartphone to use the app during the hunt. The activity fee covers all scavenger hunt activities, but you must supply your own device.
What’s the duration of the activity?
The hunt lasts approximately one hour, making it easy to fit into most holiday plans.
Where does the hunt start and end?
It begins and ends at Cathedral Square Park in downtown Milwaukee, a central and accessible location.
Can I play this activity in other cities?
Yes, Holly Jolly Hunt is designed to be played in any city, making it a portable holiday activity for travelers.
Is this activity private for my group?
Absolutely. Only your group participates, and you’ll have a remote guide via text message if needed.
Embark on this holiday adventure for a fun, memorable way to explore Milwaukee and spread some festive cheer.