Windsor: Private Dark Side Walking Tour - What You Can Expect at Each Stop

Windsor: Private Dark Side Walking Tour

Explore Windsor’s dark past with a private 1.5-hour guided walking tour, uncovering haunted sites, ghost stories, and eerie legends with an expert guide.

Discover the Spooky Side of Windsor with a Private Dark Side Walking Tour

Windsor isn’t just about royal grandeur and historic castles — there’s a shadowy, spine-tingling aspect that’s often overlooked. The Windsor: Private Dark Side Walking Tour offers an intriguing peek into the town’s more sinister stories, all told through the eyes of a local guide passionate about sharing Windsor’s haunted history. Whether you’re a history buff, a ghost story enthusiast, or just someone curious about the town’s hidden secrets, this 1.5-hour tour promises a fascinating and slightly spooky experience.

What we especially love about this tour is the focus on authentic storytelling by knowledgeable guides, who bring Windsor’s dark stories to life with enthusiasm and detail. But, keep in mind that you’ll be walking on uneven surfaces and exploring some of the more atmospheric spots, so comfortable shoes are a must. If you’re looking for a family-friendly afternoon or an engaging way to see Windsor beyond the usual sights, this tour hits the mark — just note it’s not suitable for children under 12.

Key Points
Haunted Sites: Visit the most haunted building in England and other eerie landmarks.
Authentic Stories: Led by a local guide who shares detailed legends and sightings.
Historical Insights: Learn about Windsor’s ghostly legends intertwined with royal history.
Walking Experience: A compact, 1.5-hour stroll through Windsor’s shadowy streets.
Group Size: Private group for a personalized experience.
Cost-Effective: Great value at around $168 for up to six people.

What Makes the Windsor Dark Side Tour Special

Windsor: Private Dark Side Walking Tour - What Makes the Windsor Dark Side Tour Special

This experience isn’t your typical historical walk. Instead, it zeroes in on Windsor’s most haunted locations, ghostly legends, and mysterious tales. It’s designed to give you a taste of Windsor’s eerie history, layered beneath the grandeur of its royal reputation. As you stroll through the town, your guide — who is clearly well-versed in local lore — will weave stories about phantom sightings, royal tragedies, and long-standing legends.

Authentic storytelling is a highlight here. Reviewers have mentioned guides like Eva, who they praise for her engaging narrative style. One reviewer, Elisabeth, simply stated, “Eva did a great job! Perfect tour!” This tells you that the tour’s success hinges on the guide’s ability to captivate and inform.

The Itinerary: A Walk Through Windsor’s Haunted Past

Windsor: Private Dark Side Walking Tour - The Itinerary: A Walk Through Windsor’s Haunted Past

The tour begins outside the Windsor Guildhall, a central location that’s easy to find and sets a convenient starting point. From there, the guide leads you on a route that includes key sights like Windsor Castle, but with a twist — you’ll hear about its darker history and ghostly legends woven into the scenery.

The stops — which include five additional sites — are carefully chosen to maximize storytelling potential. While the specific details of each stop aren’t explicitly listed, the experience promises to showcase Windsor’s most haunted building and sites like the gallows and royal disaster locations. You’ll walk streets that are said to be haunted by phantoms, with tales of sightings and supernatural happenings that have been passed down through generations.

The tour concludes at The Carpenters Arms, giving you a chance to reflect on the stories over a drink or meal. This ending point is conveniently located for those who want to extend their Windsor experience or head directly back to their accommodations.

What You Can Expect at Each Stop

Windsor: Private Dark Side Walking Tour - What You Can Expect at Each Stop

Windsor Castle is a key highlight. While you might think of it solely as a regal fortress, the guide will share stories of royal tragedies and ghostly visitors, adding layers of mystery to the impressive structure. The castle’s history intertwines with Windsor’s darker tales, making it a compelling stop.

As you walk the streets, expect to hear about the Windsor Witches, whose stories involve old legends of witchcraft and accusations that shook the town centuries ago. The tales of Herne the Hunter, a ghostly figure said to haunt the woods near Windsor, add an supernatural flair to the experience.

The guide’s storytelling prowess means you’ll hear vivid descriptions of sightings like the Ghost of Queen Victoria and accounts of supernatural encounters that have spooked locals and visitors alike. The stories aren’t just spooky tales; they’re woven into Windsor’s history, giving you a sense of how these legends have persisted and evolved over time.

The Experience: Atmosphere and Personal Touches

The tour’s intimate, private setting means you’ll get a more personalized experience. With just a small group, the guide can adapt their storytelling to your interests, answer questions, and dive deeper into stories that intrigue you. The guide wears a bright orange jacket, making it easy to spot in Windsor’s bustling streets.

Walking on uneven surfaces is part of the charm but also a practical consideration — sturdy shoes are essential. The tour takes place outdoors, so checking the weather forecast and dressing appropriately ensures you enjoy it comfortably, rain or shine.

The 1.5-hour duration is just right. It’s enough to hear compelling stories without feeling rushed, making it a good choice for a quick, engaging evening activity. Reviewers have noted that the tour is both fascinating and fun, with one commenting, “We saw parts of Windsor we would never have seen if it wasn’t for this tour.”

Price and Value

At around $168.37 per group for up to six people, the tour offers good value, especially considering the personalized nature of a private guide. For those interested in Windsor’s darker stories, this experience provides depth and entertainment that you might not easily find in a typical walking tour. The inclusion of a knowledgeable local guide ensures you get insightful, authentic stories, which adds to the tour’s overall appeal.

While it doesn’t include additional attractions or entrance fees to sites like Windsor Castle, the focus on storytelling and walking experience makes it a worthwhile complement to a day of sightseeing.

Who Will Love This Tour?

This tour suits travelers who have a curiosity for ghost stories, legends, and secrets behind historic sites. It’s ideal for those who enjoy stories told by passionate, knowledgeable guides and prefer small, private groups for a more personal experience. Families with children over 12, history enthusiasts, and anyone interested in Windsor’s lesser-known, spooky side will find it especially captivating.

If you’re after a fun, atmospheric way to explore Windsor beyond the usual highlights, this tour offers an engaging, memorable outing. However, if you prefer daytime activities or need a more family-friendly experience, this might be better suited as an evening adventure.

The Sum Up

The Windsor: Private Dark Side Walking Tour offers a compelling mix of history, legend, and supernatural tales in an easily accessible, 1.5-hour format. Led by a guide like Eva, who’s praised for her storytelling, you’ll gain a new perspective on Windsor — one that reveals its haunted, mysterious depths. The tour’s focus on authentic stories, coupled with the intimate group setting, makes it a standout experience for those interested in the town’s darker myths and legends.

While it’s not a comprehensive historical tour of Windsor’s grandeur, it provides a fascinating, ghostly complement to your visit. The value for the price lies in the personalized storytelling and the chance to see Windsor through a different lens, exploring its shadows and secrets.

This experience is particularly well-suited for curious travelers, history and ghost story lovers, or anyone wanting an evening of spooky fun with a knowledgeable local. Just remember to wear comfortable shoes and prepare for a walk on uneven surfaces — the stories are worth it.

✨ Book This Experience

Windsor: Private Dark Side Walking Tour



5.0

“The whole group loved this tour. With a wonderful storyteller and guide. We saw parts of Windsor we would never have seen if it wasnt for this tour…”

— Rasmus, April 24, 2025

FAQ

How long is the tour?
The tour lasts approximately 1.5 hours, making it a manageable and engaging experience without being overly lengthy.

Where does the tour start and end?
It begins outside Windsor Guildhall, where your guide, in a bright orange jacket, will meet you, and ends at The Carpenters Arms, a convenient spot for refreshments afterward.

Is this tour suitable for children?
It’s not recommended for children under 12, mainly because of the spooky themes and walking on uneven surfaces.

What’s included in the price?
The tour includes a private, guided 1.5-hour walk led by an expert local guide. It does not include entrance fees to sites or food and drinks.

Can I cancel the booking?
Yes, you can cancel up to 24 hours in advance for a full refund, offering flexibility if your plans change.

Is it wheelchair accessible?
Yes, the tour is wheelchair accessible, but since it involves walking on uneven surfaces, it’s worth confirming specific needs at booking.

How many people can join?
This experience is designed for private groups up to six people, providing an intimate setting for storytelling.

Do I need to book in advance?
Yes, booking ahead is recommended to secure your spot, especially during peak tourist seasons or weekends.

All in all, if you’re after a unique, ghostly perspective on Windsor and a tour led by a passionate guide, this dark side walk offers a memorable journey into the town’s hidden shadows.