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Explore Halifax's hidden history on a private walking tour with stories of bootleggers, privateers, and harbor secrets, led by local guide Jimmy Dalling.
Discover the darker side of Halifax with the Halifax Like a Local Darkside Walking Tour. Priced at $486.77 per group (up to 8 people), this 2 to 2.5-hour private experience offers an intimate look into the city’s lesser-known stories. Led by the charismatic Jimmy Dalling, a local with deep roots in Nova Scotia, this tour promises a personal connection and engaging storytelling that brings Halifax’s secret past to life. From contraband shipwrecks to harbor smuggling and tales of privateers, the tour covers a variety of fascinating topics, making it ideal for history enthusiasts eager to go beyond the usual tourist spots.
While the tour focuses on intriguing and sometimes messy stories of Halifax’s past, it also includes visits to notable landmarks, with ferry rides and stops at key locations. The small-group format ensures a cozy, personalized experience, perfect for those who prefer a relaxed pace and the chance to ask questions. The tour’s unique emphasis on local history, maritime lore, and hidden scandals makes it stand out from more conventional city walks.


This private tour in Halifax emphasizes hidden histories and local secrets. It departs from The Emigrant Statue at 1215 Marginal Rd and ends back at the same point, offering a well-rounded exploration of the city’s lesser-known past. The tour is designed for those interested in maritime stories, scandals, and stories of contraband, with Jimmy Dalling sharing insights that challenge the typical tourist narrative.
The experience balances walking, ferry rides, and storytelling, making it suitable for those with moderate physical fitness. The tour operates every day from 8:00 AM to 8:30 PM, and confirmation is immediate upon booking. It is a fuelled by curiosity and local knowledge, perfect for visitors who want to uncover Halifax’s messier, fascinating history.
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The tour begins with a visit to the islands in Halifax Harbour, touching on their history for both settlers and the Mi’kmaq. You learn why the opposite side of the harbour is called ‘The Darkside’, setting the tone for stories of intrigue and maritime mystery. This initial stop introduces visitors to the harbour’s layered past, blending Indigenous history with colonial tales.
The journey continues with stories of shipwrecks, contraband, and smuggling, drawing attention to Halifax’s reputation as a hub for bootlegging and privateering. These stories reveal the messy side of the city’s maritime activity, often hidden from mainstream narratives.

Throughout the tour, you visit spots with excellent exhibits on significant events like the Titanic, the Halifax Explosion, and the Age of Sail. These stops provide context to Halifax’s maritime importance, while the guide shares stories of old scandals and privateer exploits not found in standard history books.
The stops also highlight the last Flower Class Corvette, where insights are shared about its use during wartime and a personal story involving a family member who served aboard her. These stories deepen the understanding of Halifax’s military and naval history.

A highlight of the tour is the ferry ride on the oldest continuously operating saltwater ferry in North America. The 30-minute trip includes learning about the ferry’s history, the harbour bridges, and the curse believed to have originated from love and intrigue. This ferry ride transforms the tour into a true maritime adventure, offering scenic views and historical insights.
The ferry ride is included, emphasizing the unique nature of this experience as a kind of “ocean cruise” that combines transportation and storytelling seamlessly.

At Alderney Landing, the tour takes a deeper dive into the stories that shaped Halifax and Dartmouth. This stop lasts about 30 minutes and includes free admission, allowing visitors to appreciate local history beyond just Halifax proper.
Here, stories of local legends, notable figures, and historic events fill the air. The guide distills complex histories into engaging tales, giving context to Halifax’s development as a city of maritime commerce and social change.

Returning to the ferry for a second ride, travelers hear the stories behind the current ferries and explore the unruly origins of some of Canada’s major institutions. This 20-minute ferry trip acts as both transportation and storytelling, emphasizing Halifax’s maritime roots and its influence on the nation’s development.
The ferry’s history and the stories behind its vessels create a tangible link to Halifax’s ongoing relationship with the sea.

Next, the tour visits Province House, where stories of the first Canadian Separatist, freedom of the press, duels, and the “great contradiction” unfold. The hidden architectural features of the building are also explored, revealing layers of political and social history.
A brief stop at St. Paul’s Anglican Church follows, where the oldest building in Halifax shares remarkable secrets. The parade square, the old morgue, and the Old Town Clock are all part of the story, adding a historic and architectural dimension to the tour.

The Old Burying Ground stands as the oldest cemetery in Halifax and offers stories of public executions, personal connections, and notable monuments. This stop, lasting approximately 5 minutes, provides a poignant glimpse into Halifax’s more dramatic past and the lives of those who shaped the city.
The guide shares stories of last public hanging and explains the significance of individual monuments, enriching the historical narrative.
The tour wraps up with stories of how everything went wrong, turned around, and went backwards, uncovering the city’s messy origins and subsequent evolution. This narrative offers a full-circle perspective, from the city’s turbulent past to its current identity.
Finally, the tour concludes with a warm welcome to Halifax, emphasizing that the city is home to a complex, fascinating history that is best appreciated through stories of both scandal and resilience.
The Halifax Like a Local Darkside Walking Tour offers a well-rounded, private experience that combines historical landmarks, maritime stories, and local legends. Its small-group format ensures an intimate connection with Jimmy Dalling, whose storytelling brings personal warmth and depth to each tale.
This tour is especially suited for those interested in secret histories, maritime lore, and off-the-beaten-path stories. The inclusion of ferry rides and stops at notable historic sites makes it a comprehensive yet relaxed way to explore Halifax’s darker past—all for a reasonable price given the personalized experience.
While it excels in storytelling and authenticity, it requires moderate physical fitness due to the walking and ferry components. It’s ideal for those looking for a deep dive into local secrets, with lots of opportunities to ask questions and explore at your own pace.
“Jimmy is warm, informative and very entertaining. It was honestly like spending the day with family. We learned alot about the area. Hi also ta…”
Is this tour suitable for families?
Yes, as long as family members are comfortable with walking and ferry rides. It’s a private tour, so arrangements can be tailored if needed.
How long are the ferry rides included in the tour?
There are two ferry rides, lasting 30 minutes and 20 minutes, respectively, with storytelling embedded during each trip.
What makes this tour different from other Halifax sightseeing options?
It focuses on hidden stories of contraband, privateers, and scandals rather than just landmarks. Led by a local storyteller, it offers a personal, intimate perspective on Halifax’s off-the-beaten-path history.
Can I book this tour on short notice?
Yes, as the tour operates daily and confirmation is immediate upon booking. It’s a private experience, so availability depends on group size.
What should I wear or bring?
Comfortable walking shoes are recommended. The tour provides bottled water, but coffee or snacks are not included, though stops for coffee are common during the tour.
This Darkside Walking Tour in Halifax promises a fascinating journey into the city’s shadowy past, offering personal stories and unique sights that reveal a different side of Halifax’s history.