Overview
Available languages
Mobile ticket
Delve into Halifax's hidden history on this engaging walking tour, where tales of bootleggers and privateers come to life. Led by Jimmy Dalling, a local storyteller with deep roots in Nova Scotia, uncover the secrets that shaped the city beyond the tourist spots. Over 1.5 to 2.5 hours, explore off-the-beaten-path locations and hear stories of contraband shipwrecks and harbor smuggling. This intimate tour is designed for small groups, ensuring a personal experience filled with the messy, fascinating history of Halifax.
- Private tour ensures a personal touch and time to ask questions
- Discover Halifax's hidden history with a local expert guide
- 1.5 to 2.5-hour intimate walking tours and ferry rides
- Hear tales of bootleggers, privateers, and old scandals
- Discover the best Halifax has to offer efficiently with an expert
Additional Info
Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Not recommended for travelers with poor cardiovascular health
Travelers should have at least a moderate level of physical fitness
What To Expect
We'll pass and touch on the history of the islands in the harbour, learn more about the harbour, it's history for both settlers and Mi'kmaq as well as why the opposite side of the harbour is called 'The Darkside'.
Maritime Museum of the Atlantic
Features excellent exhibits on the Titanic, the Halifax Explosion and age of Sail - all to be explored on your walk
Options
Halifax Like a Local Darkside Walking Tour
What‘s Included
We take the longest consistently operating salt water ferry in North America - the world's cheapest ocean cruise!
We typically stop for coffee and a snack. Your guide will have bottles of water but they are fuelled by caffeine and love it when you buy them a coffee!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reviews
3 reviews
Total reviews and rating from Viator & Tripadvisor
Fantastic tour around the Halifax & Dartmouth waterfront
gdub21,Jan 20, 2026
- Review from Tripadvisor
5.00This tour felt like being shown around by a hilarious friend who actually knows what they’re talking about. A Ride to the Darkside gave us a totally different view of Halifax—especially once we crossed to Dartmouth. My partner and I got great harbour views, solid context, and a bunch of details we never would’ve found on our own. The stop at the Halifax explosion memorial looking out at Downtown Halifax & the MacDonald bridge was the highlight. Highly recommend for couples or small groups.
A Scenic Tour Full of Heart and Humour
Q2285BRjeffc,Jan 17, 2026
- Review from Tripadvisor
5.00In July of 2025 We booked a tour with “A Ride to the Darkside” because we were looking for a tour that was smaller and more personal than the usual tourist options. We were not disappointed. Right from the start Jimmy made it feel like we were stepping into a story rather than being marched through a checklist of things to see. The ferry crossing was surprisingly an emotional moment, the breeze, the harbour and skyline were magnificent. What I liked the most was how Jimmy connected the big harbour “facts” to human stuff. The why people live where they live and how the city got its personality. These are the kind of details that Jimmy was able to pass on to us and it made the experience so much more enjoyable. Jimmy’s story about the twelve green bananas is a story we have shard with all of our friends since returning home. If you want a tour of Halifax full of heart and humour, this is it.
Worth the money
Margaret E,Aug 30, 2025
- Review from Viator
5.00Jimmy is warm, informative and very entertaining. It was honestly like spending the day with family. We learned alot about the area. Hi also takes good pictures! Only wish there was more on the bootlegging and lore!
Related Experiences
Operated by Darkside Tours