Keegan McGregor

The Path

Bar training often starts in rooms where speed, listening, and composure have to develop together. Keegan McGregor first worked as bartender at The Adelaide Oyster House in St. John’s, NL, a setting that put him inside the cadence of service: conversation, orders, guest comfort, and detail moving at the same time. He then continued as bartender at Field Guide, where that early service fluency carried into a sharper command of hospitality and drink. Cocktail work in those rooms was not only technical. It taught how a drink can carry place, how a joke can change the temperature of a room, and how a small act of attention can make a short visit register. Today, as Beverage Director of Highwayman, Keegan McGregor applies that same poise and precision to a program defined by confidence, character, and a clear sense of place.

The Work Today

The bar practice is built around storytelling, sustainability, and community, with a stated specialty that keeps the register plain: Maritime hospitality, bad jokes, and ice cold martinis. In Keegan McGregor’s hands, that phrase describes a working style where technique is present but not performed for its own sake, and where ease at the bar is treated as part of the build. At Highwayman, cocktail-forward hospitality is kept precise and unpretentious. The service model is casual and welcoming in an Atlantic Canadian register, with attention placed on the guest rather than on display. The drinks can be bracing, savoury, seasonal, and playful, but the anchor remains the person across the bar. The Olive Leaf Martini shows the house approach to a dirty martini: inspired by the Bamboo and made with olive-leaf-infused gin for a subtly grassy sip that is not too salt-heavy. Coming Home works in another register, as a smoky and savoury cocktail that pairs well with earthy, umami-rich dishes. Both examples point to Keegan McGregor’s preference for flavour that opens gradually rather than arriving all at once. Seasonal thinking is handled in concrete ingredients rather than abstraction. "For the Hodge Podge Flip, I was thinking of fall instead of spring, so I naturally had to use corn milk, carrots, and ginger." On tour, another popular drink is described with the same specificity: "One of my most popular cocktails on tour is the “Apple Butter Martini” — a combination of Tanqueray 10 Gin, Pineapple Weed Vermouth, and an Apple Butter Liqueur." The language stays close to memory, seasonality, and the flavours that make a place recognizable.

Signature

Keegan's signature dishes include Hodge Podge Flip, Apple Butter Martini, Highwayman’s Olive Leaf Martini, Coming Home, and Crème Fraîche Vesper.

In Their Words “Being able to connect with strangers has also been one of my favourite parts of the job. We have a chance to learn from one another, or if anything, share a laugh.” “When I think of the taste of Halifax, I think more in terms of seasonality, or simply the food my family would make — dishes with interesting flavour combinations.”

Acclaim

Keegan's honors include World Class Global Bartender of the Year (2024).