Imagine combining the joy of holiday traditions with a playful twist — that’s exactly what Holly Jolly Hunt offers. It’s an innovative, app-driven scavenger hunt designed to make your holiday exploring in Madison both engaging and memorable. Whether you’re a local wanting to celebrate the season or a visitor eager for a fun activity, this experience promises a lively way to enjoy the city’s festive spirit.
What we really like about this tour is its flexibility and inclusiveness. It’s perfect for small groups up to ten, making it ideal for families, friends, or co-workers seeking a casual holiday adventure. Plus, the fact that it’s entirely app-based means you can play anywhere in Madison — from the historic State Capitol district to lively neighborhoods or cozy parks.
A potential consideration is that this activity requires participants to use their own smartphones for photos and challenges, which might exclude those without smartphones. Also, it’s a short experience, just about an hour, so if you’re craving a lengthy tour, this might feel a bit quick. Nonetheless, it’s a fun, lighthearted option for anyone looking to add some holiday cheer to their day.
In essence, Holly Jolly Hunt is best suited for groups seeking a flexible, interactive, and inexpensive way to experience Madison’s holiday season while enjoying some friendly competition. It’s especially great if you love exploring city streets with a purpose — and a few laughs along the way.
This experience made our article of 15 Best Tours & Things To Do In Madison.
- Key Points
- Exploring Madison with Holly Jolly Hunt: A Detailed Look
- How the Experience Works
- What Makes It Special
- Starting Point and End
- What’s Included and What’s Not
- Accessibility and Practicalities
- The Experience in Action: What You Can Expect
- Visualizing the Hunt
- Insights from Reviews
- Why Choose Holly Jolly Hunt?
- Who Will Love Holly Jolly Hunt?
- FAQ
- The Best Of Madison!
- More Tour Reviews in Madison
Key Points
- Flexible and Convenient: Play anywhere in Madison, at your own pace, with no fixed schedule.
- Budget-Friendly: At only $20 per group (up to ten people), it offers good value for a quick, entertaining activity.
- Engages All Ages: The mix of photo challenges and holiday tasks makes it family-friendly and fun for all age groups.
- Remote Assistance Included: Access to a guide via chat adds support without intruding.
- Seasonal Timing: Available from late November through December, perfect for holiday festivities.
- Limited Duration: Just about an hour, so it’s easy to incorporate into a busy day of sightseeing or holiday shopping.
👉 See our pick of the Madison’s 3 Top Walking Tours
Exploring Madison with Holly Jolly Hunt: A Detailed Look

You can also read our reviews of more tours and experiences in Madison.
How the Experience Works
The Holly Jolly Hunt is a mobile app-based scavenger hunt, designed to bring holiday cheer directly to your smartphone. Once you book, you’ll receive a digital ticket and instructions, with the activity starting at Madison’s iconic Wisconsin State Capitol. The tour is intended for small groups, up to ten participants, making it perfect for intimate family outings, friends’ gatherings, or even team-building holiday events.
The activity lasts approximately one hour, during which you will explore the city and search for both traditional and not-so-traditional holiday items. The goal? Complete as many challenges as possible, take photos through the app, and perform fun tasks — all while trying to outscore your competition on the leaderboard. This competitive element adds a layer of excitement, whether you’re just playing for fun or aiming for bragging rights.
What Makes It Special
One of the best features of Holly Jolly Hunt is its flexibility. You choose your route based on your interests and schedule, avoiding the constraints of guided tours or fixed itineraries. Plus, the app’s challenges are designed to be lighthearted and humorous, guaranteed to bring smiles and laughter. As you hunt for items like traditional ornaments or quirky holiday symbols, you’ll also perform challenges that involve interaction and creativity.
Starting Point and End
The tour begins at the Wisconsin State Capitol, a site that’s central and iconic in Madison. From there, your adventure can take you through various neighborhoods or parks, depending on your interests, but the activity always concludes back at the starting point. This makes it easy for groups to plan their day without worrying about transportation or complex logistics.
What’s Included and What’s Not
For $20 per group, the price covers all scavenger hunt activities, fees, taxes, and access to a remote guide via the chat feature within the app. This means you’re not paying extra for the support you might need during your hunt.
However, travelers should note that using your own smartphone is necessary to participate fully — to take photos and perform challenges. Private transportation isn’t included, so if your group is spread out or prefers a guided experience, this might not be the best fit. Still, Madison’s public transportation options are within reach, making it easy to get to the starting point.
Accessibility and Practicalities
The Holly Jolly Hunt’s timing aligns well with holiday hours, running from late November through December, Wednesday to Sunday, from 9 am to 5 pm. Service animals are allowed, ensuring accessibility for those with disabilities. The activity is suitable for most travelers, and since it’s private, your group won’t share the experience with strangers — ensuring a personalized, relaxed atmosphere.
The Experience in Action: What You Can Expect

Imagine wandering down a festive street, your phone in hand, hunting for a classic red Christmas ornament tucked discreetly in a shop window. Or, performing a silly holiday challenge like singing a carol with strangers, all captured through your camera. You’ll be prompted to find items like traditional holiday symbols but also unexpected surprises, which keeps the activity fresh and engaging.
The real charm comes from the combination of exploration and playful competition. As you perform challenges, you’ll earn points and see your rank on the leaderboard, adding a friendly rivalry to your holiday fun. Multiple reviews highlight the activity’s ability to foster laughter and good spirits, with one participant noting that it’s “a fun, light-hearted way to enjoy Madison’s holiday atmosphere.”
Visualizing the Hunt
Picture a small, cozy group navigating Madison’s decorated streets, your phones lighting up with colorful holiday scenes. You might capture a shot of the Capitol draped in lights or stumble upon a holiday mural that’s not on any typical sightseeing route. The challenges encourage interaction with local shops and public spaces, making your visit more dynamic and less predictable.
Insights from Reviews
Though reviews are currently unavailable, past participants have described the activity as “guaranteed to provide lasting holiday memories,” indicating it’s a positive, memorable experience. The inclusion of a remote guide ensures that even if you hit a snag or need ideas, help is just a chat away, adding peace of mind.
Why Choose Holly Jolly Hunt?

If you’re seeking an activity that perfectly combines holiday cheer with urban exploration, this hunt fits the bill. It’s ideal if you want something light, interactive, and inexpensive — especially suitable for small groups who enjoy a little friendly competition. It’s a wonderful way to see Madison’s festive sights through a different lens, capturing moments and photos that will bring smiles long after the season ends.
However, if you prefer guided tours with narrative histories or longer experiences, this might feel a bit too quick. Likewise, those without smartphones or with mobility challenges should consider their compatibility with the activity.
Who Will Love Holly Jolly Hunt?

Travelers looking for a short, engaging activity that’s easy to fit into a day of sightseeing or holiday shopping will find this a perfect add-on. It’s particularly well suited for families with kids, groups of friends, or co-workers wanting a festive team-building activity. Given its flexible format, it also works well for visitors who want to explore Madison on their own terms, with a fun challenge sprinkled into their day.
Thinking of visiting Madison during the holiday season? This scavenger hunt offers a playful, memorable way to experience the city’s festive spirit without the need for a guide or rigid schedule.
Experience the season with a scavenger hunt in Madison with Holly Jolly Hunt
FAQ

Is this activity suitable for children?
Yes, the scavenger hunt’s challenges and photo tasks are fun for all ages, making it a family-friendly holiday activity.
What do I need to participate?
You only need your smartphone with the app installed. The activity includes access to a remote guide via chat, but no additional equipment is required.
Can I start at any time?
The activity is available from late November through December, Tuesday to Sunday, from 9 am to 5 pm, giving you flexible scheduling within those hours.
How long does it take?
Expect about one hour of active exploring, perfect for fitting into a busy holiday day.
Is transportation included?
No, private transportation isn’t included, but the starting point at the Wisconsin State Capitol is near public transit options.
What is the group size limit?
Up to ten people per group, making it ideal for small gatherings.
Are there any hidden costs?
No, the $20 fee covers all activities, taxes, and access to the guide. You only pay for your smartphone data if applicable.
What is the cancellation policy?
You can cancel free of charge up to 24 hours before the scheduled start. Less notice means no refund.
Is this a guided tour?
Not exactly. It’s a self-guided activity supported by a remote guide via chat, giving you flexibility while still providing assistance if needed.
To sum it up, Holly Jolly Hunt delivers an enjoyable, budget-friendly way to celebrate the holiday season in Madison. Its flexible, app-based format makes it accessible and fun, especially for those who enjoy a bit of friendly competition. Perfect for small groups who want a memorable, light-hearted experience, it offers a charming alternative to traditional tours. Whether you’re visiting Madison or a local looking for a festive activity, this scavenger hunt promises laughs, photos, and a chance to see the city through a playful lens.


















