Holiday Scavenger Hunt in Windsor by Holly Jolly Hunt
If you’re looking for a way to add some holiday cheer to your visit to Windsor, Ontario, the Holly Jolly Hunt offers a lighthearted, interactive adventure at an affordable price. For just about $20 per group, you and up to nine others can spend roughly an hour exploring the city’s streets, searching for holiday-themed items, and completing silly challenges—all via an easy-to-use smartphone app. This activity is perfect for families, friends, or co-workers wanting to combine sightseeing with some festive fun.
What immediately draws us in is the simplicity of the setup: a mobile ticket that requires no complicated logistics or transportation, just your group and a smartphone. Two things we really appreciate are the flexibility to play anytime between late November and New Year’s Eve, and the chance to create memorable holiday moments while exploring Windsor’s streets. The only consideration? Since the activity is largely app-based and involves walking, those with mobility issues or limited stamina might find it a bit demanding.
This scavenger hunt is especially suited for groups who enjoy casual, playful experiences—think of it as a holiday-themed treasure hunt with a modern twist. If you’re traveling with kids, friends looking for a fun activity, or a family wanting to enjoy Windsor’s festive ambiance without the usual tourist crowds, this activity could be just the ticket.
Key Points
- Flexible Play: Can be done anytime within the holiday season, Tuesday through Sunday.
- Family-Friendly: Suitable for all ages, with silly challenges and festive photo ops.
- Affordable: Around $20 for up to 10 people, with all fees and taxes included.
- App-Based Convenience: No need for physical tickets or guides—just your smartphone and a good attitude.
- Remote Support: One hour of guidance via text ensures help is available if needed.
- City Exploration: Combines sightseeing with fun challenges, making it a memorable part of your Windsor visit.
A Detailed Look at the Windsor Holiday Scavenger Hunt

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An Introduction to the Experience
When we first heard about Holly Jolly Hunt, we liked the idea of blending sightseeing with a playful holiday activity. Playing with friends or family, all from the comfort of your own device, makes it accessible and easy to fit into any schedule. The activity starts at 78 Riverside Drive West, a spot that’s easy to reach via Windsor’s public transportation, and ends right back where you started, making it a convenient loop.
This scavenger hunt isn’t just about ticking off traditional items like Christmas trees or Santa hats. It encourages discovery of more unique and unexpected holiday sights around Windsor, which adds a layer of surprise and delight.
The Itinerary and Key Stops
While the specific stops aren’t detailed in the information, the concept involves exploring the town’s streets for holiday-related items, both classic and quirky. You might find yourself looking for familiar sights like wreaths or decorated storefronts, as well as more playful challenges—perhaps capturing a photo with an unusual decoration or performing a Christmas-themed task.
What makes this appealing is the balance between structured scavenging and spontaneous exploration. You’ll get points for each item or task completed, and the main goal is to amass as many points as possible. The leaderboard feature adds a friendly competitive edge, encouraging teamwork and laughter.
What the App Brings to the Table
The app simplifies the entire process—no paper maps or guides needed. It guides your team from one location to the next, displaying the list of items and challenges. The ability to take photos directly through the app streamlines scoring and keeps everything organized. The inclusion of silly holiday challenges ensures that the mood stays fun and light.
Support and Practicalities
A major plus is the remote guide via text message. We found this reassuring—if you get stuck or need a hint, a quick message can help you keep the fun going without frustration. The duration—approximately one hour—is perfect for a quick holiday activity that doesn’t take up an entire day.
Since the activity costs only $20.44 per group, it’s a budget-friendly way to add some local flavor and festive spirit to your trip. All taxes and fees are included, meaning no hidden costs. However, you’ll need your own smartphone, and if your group isn’t local, transportation to and from the start point is not included.
The Experience in Practice
Imagine walking down Windsor’s streets, pointing your phone at a brightly decorated shop window or a giant snowman sculpture, snapping a photo, and giggling as you attempt to perform a goofy holiday challenge—perhaps singing a Christmas carol or balancing a candy cane on your nose. The app keeps score and displays your rank, turning what could be a simple walk into a friendly competition.
One reviewer mentioned that this experience “guarantees lasting holiday memories,” and that’s exactly what we think makes it special. It’s not just about finding items; it’s about sharing laughs and making spontaneous, joyful moments.
Who Will Love This?
This activity is ideal for families with kids, as the challenges are designed to be fun and light-hearted. It’s also great for groups of friends or coworkers wanting a festive team-building activity. If you enjoy exploring a city with a playful twist and appreciate the convenience of an app-guided experience, you’ll find this scavenger hunt a delightful way to see Windsor.
Considerations and Tips
- Make sure everyone has a charged smartphone and enough battery for about an hour of activity.
- Wear comfortable shoes—you’ll be walking through Windsor’s streets, possibly in cold weather.
- Since it’s a flexible schedule, consider playing during daylight hours for the best visibility and photo opportunities.
- Keep an eye on the leaderboard for some friendly competition and extra motivation.
Final Thoughts
The Holly Jolly Hunt in Windsor offers a simple, engaging way to enjoy the city during the festive season. Its blend of traditional holiday sights and fun challenges makes it a great choice for creating meaningful memories without breaking the bank. The fact that it’s flexible, family-friendly, and app-based means it’s accessible for many different travelers and groups.
While it might not be the most in-depth cultural tour, it shines as a lighthearted, interactive experience that adds a touch of whimsy to your holiday visit. Whether you’re a local looking for a new way to celebrate or a visitor wanting to explore Windsor’s holiday spirit, this scavenger hunt provides a joyful, memorable outing.
FAQs

How long does the Holly Jolly Hunt last?
The activity is approximately 1 hour long, making it easy to fit into a busy sightseeing day or as a quick holiday break.
What is included in the price?
The fee covers all scavenger hunt activities, all taxes and fees, and one hour of remote guidance via text message to help guide your team.
Do I need to bring my own smartphone?
Yes, the activity requires your own activity-owned smartphone to participate and take photos through the app.
Is transportation included?
No, private transportation is not included. You will need to manage your own transport to and from the starting point.
Can I cancel the activity?
Yes, there is free cancellation available if you cancel at least 24 hours in advance, allowing a full refund.
What are the opening hours?
The activity is available from late November through December 31st, Tuesday to Sunday, 9 AM to 5 PM.
Is this suitable for children?
Yes, the activity is designed to be fun for all ages, with silly challenges and photo opportunities that kids will enjoy.
Is it accessible for people with disabilities?
Most travelers can participate, but those with mobility issues should consider the walking involved.
Can I play this activity in other cities?
Absolutely! The Holly Jolly Hunt is designed to be played in any city, so you can enjoy it wherever you travel.
This holiday season, give yourself permission to enjoy Windsor in a playful, relaxed way with Holly Jolly Hunt—creating memories that are funny, festive, and uniquely yours.
More Tour Reviews in Windsor
- Explore Windsor with a Unique Scavenger Hunt by Crazy Dash
- Scavenger Hunt Adventure in Windsor by Wacky Walks
- Windsor City Scavenger Hunt by Zombie Scavengers
- Private Scenic Riverside and Nature Walking Tour in Windsor
- London: Windsor Castle Private Tour with Hotel Transfers
- From London: Windsor, Stonehenge & Bath Private Car Tour
More Windsor experiences we've covered
- Explore Windsor with a Unique Scavenger Hunt by Crazy Dash
- Scavenger Hunt Adventure in Windsor by Wacky Walks
- Windsor City Scavenger Hunt by Zombie Scavengers
- Private Scenic Riverside and Nature Walking Tour in Windsor
- The Top 4 Windsor Walking Tours
- Our Picks For The 11 Best Tours In Windsor
- London: Windsor Castle Private Tour with Hotel Transfers
- From London: Windsor, Stonehenge & Bath Private Car Tour
- Windsor: Golden Tours Open Top Hop-on Hop-off Bus Tour
- Windsor Town Daily Walking Tour (11am & 2pm)
- Windsor Castle with Pub Lunch and Private Transfer
- Royal Windsor Castle Tour Private including tickets
