Experience the season with a scavenger hunt in Madison with Holly Jolly Hunt
Imagine wandering through Madison’s charming streets, camera in hand, searching for holiday-themed surprises, all while competing for bragging rights. That’s exactly what Holly Jolly Hunt offers—a playful, interactive way to explore the city during the holiday season. For just $20 per group, you get around an hour of lively, holiday-themed fun, suitable for groups of up to ten people.
What we love about this experience is how flexible and engaging it is. First, it’s entirely app-based, meaning you can play anywhere in Madison that suits your mood—whether that’s the historic downtown, near the Wisconsin State Capitol, or even your own neighborhood if you prefer a more private outing. Second, the challenges are designed to be light-hearted and inclusive, making this a perfect activity for families or co-workers looking for a holiday boost.
A potential consideration is that this activity requires a smartphone to participate, so travelers without a compatible device might find it less accessible. Also, since it’s a self-guided scavenger hunt with remote support, some might prefer a more structured or guided tour. Still, for those comfortable with the tech, this offers excellent value and flexibility.
This experience is best suited for groups of friends, families, or coworkers who enjoy a mix of adventure and holiday cheer. If you’re looking for a fun, low-cost way to create lasting memories in Madison, Holly Jolly Hunt offers a genuinely authentic seasonal experience.
Key Points

- Flexible Location: Play anywhere in Madison, making it ideal for different interests and schedules.
- Affordable Price: At $20 per group, it offers a budget-friendly way to enjoy the holidays.
- Engaging Challenges: Includes photo tasks and fun challenges that spark laughter and team spirit.
- Remote Assistance: Access to a guide via chat ensures support without needing a tour guide physically present.
- Suitable for All Ages: Most travelers can participate, and service animals are allowed.
- Private Experience: Only your group will participate, making it personalized and relaxed.
Exploring Madison with the Holly Jolly Hunt

Madison during the holiday season can be magical, filled with twinkling lights, festive markets, and historic architecture. Holly Jolly Hunt taps into this charm by turning your exploration into a game—adding a layer of fun you’d be hard-pressed to find in a typical walking tour. It’s perfect for those who prefer a laid-back, playful approach to sightseeing rather than structured guided walks.
What does the hunt involve? You’ll download an app that guides you through a series of holiday-themed challenges. These can include spotting traditional ornaments on a storefront, finding whimsical or not-so-traditional decorations, or completing amusing challenges along the way. The app scores your team based on the photos you take and the tasks you complete, which are then displayed on a friendly leaderboard—a feature that adds a competitive edge to keep everyone motivated.
The route itself is flexible; you choose your own adventure, which means you could spend more time in a part of town you love or try to hit as many spots as possible in a limited time. The activity benefits from Madison’s walkable city center, near the State Capitol, parks, and lively neighborhoods, so it’s easy to keep the pace light and enjoyable.
The app’s chat feature provides access to a remote guide, who can help if you get stuck or need clarification. This support system is handy, especially if you’re playing with kids or less tech-savvy members of your group. The activity includes all the scavenger hunt tasks and fees, with the only extras being your own smartphone and transportation to the starting point.
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What to Expect from the Holly Jolly Hunt

The activity begins at the Wisconsin State Capitol, an iconic Madison landmark and a beautiful setting to kick off your holiday adventure. From there, the hunt takes you through streets lined with historic buildings, glowing storefronts, and cozy cafes—all decked out for the season.
Duration: About an hour, making it a perfect break in your day or an enjoyable evening activity.
Group Size: Up to ten people, which strikes a nice balance—large enough for lively energy but small enough to keep it intimate and manageable.
Timing: Open from late November through December 31, during weekday and weekend hours (9:00AM to 5:00PM). That means you can fit it into a shopping day, a date, or a family outing without hassle.
Meeting Point: The adventure starts right at the State Capitol, with an end point that’s the same as your starting location, so no need for complicated logistics.
Cost: At $20 per group, it’s remarkably good value—especially considering all the fun and memory-making potential packed into that hour.
Note: You’ll need to have your own smartphone to participate, and private transportation isn’t included, so be prepared to walk or arrange your own way to the start.
The Experience in Action – Authenticity and Fun
Based on feedback, one of the biggest draws is how accessible and inclusive the activity is. “We loved the way it combined sightseeing with playful challenges,” a reviewer remarked, highlighting how it brought out laughter and shared joy. The activity’s design to be “guaranteed to provide lasting holiday memories” rings true when you see families and friends embracing the spirit of the season.
The photo challenges are simple but effective at encouraging creativity—think of snapping a selfie with a giant wreath or capturing a quirky holiday display. The competitive element, with scores displayed on the leaderboard, encourages friendly rivalry, making the activity engaging for all ages.
The remote guide support is a smart feature, especially since some reviews note it’s reassuring to have help available without a physical guide present. This flexibility allows you to take your time and enjoy the experience at your own pace.
One review mentioned, “It’s perfect for those who want to explore at their own speed but still have support when needed,” which sums up the charm of this activity nicely.
The Practical Side – What You Need to Know

Price: At $20, this activity offers great value, especially since all scavenger hunt activities, fees, and taxes are included.
Duration: About 1 hour, making it easy to incorporate into a day’s sightseeing or holiday schedule.
Group Size: Up to ten people, which works well for families, friends, or small teams.
Booking: Book well in advance—on average, 28 days ahead—to secure your spot during the busy holiday season.
Accessibility: Service animals are allowed, and most travelers can participate. Just remember, you’ll need a smartphone and some familiarity with simple app use.
Cancellation: Free cancellation up to 24 hours in advance provides peace of mind for planning.
Who Will Love Holly Jolly Hunt?

If you enjoy lighthearted outdoor adventures and want to experience Madison’s holiday ambiance in a playful way, this scavenger hunt is a perfect fit. It’s especially suited for groups seeking flexibility, affordability, and fun. Families with kids, friends looking for a festive activity, or co-workers wanting to build holiday team spirit will find this a delightful option.
Those who prefer a more structured tour might find it too informal, but for those wanting to explore at their own pace with a splash of friendly competition, this activity hits the spot. It also works well for travelers who don’t mind using their smartphones for navigation and photo tasks.
The Sum Up

Holly Jolly Hunt in Madison offers a charming, engaging, and budget-friendly way to celebrate the holiday season. It’s designed for those who enjoy a bit of adventure mixed with seasonal cheer, all set within Madison’s picturesque streets. The app-based format and flexible timing make it accessible for a wide range of travelers, while the inclusive, family-friendly challenges ensure everyone can join in on the fun.
For anyone seeking a memorable, authentic holiday activity that combines exploration with friendly competition, Holly Jolly Hunt delivers. It’s a light-hearted way to see Madison’s festive side and create stories worth sharing—whether you’re visiting with loved ones, friends, or colleagues.
If you love holiday traditions, enjoy outdoor activities, or just want a different way to experience Madison’s seasonal charm, this scavenger hunt is worth considering. It’s a simple, enjoyable way to add a little extra sparkle to your holiday travels.
FAQ

How much does the Holly Jolly Hunt cost?
It costs $20 per group, with a maximum of ten participants, which makes it an affordable way to enjoy the season together.
How long does the activity last?
The scavenger hunt takes approximately 1 hour, making it easy to fit into your day or evening plans.
Where does the activity start and end?
It begins and ends at the Wisconsin State Capitol, central to Madison’s holiday sights and easily accessible.
Do I need my own smartphone?
Yes, the activity is app-based, so a smartphone is required to play and take photos for scoring.
Are there any restrictions on who can participate?
Most travelers can participate; service animals are allowed. The activity is suitable for groups up to ten people.
Can I cancel if my plans change?
Yes, you can cancel free of charge up to 24 hours before the scheduled start time for a full refund.
In sum, Holly Jolly Hunt combines the joy of holiday tradition with a modern, flexible twist. It’s a lighthearted way to explore Madison’s festive streets, perfect for those who love a bit of friendly competition and authentic seasonal fun.
