Keegan McGregor

Keegan McGregor is Beverage Director at Highwayman in Halifax, Nova Scotia, where his work is rooted in Atlantic Canadian hospitality, warm without fuss, precise without stiffness, casual in tone, and attentive in practice. His approach is practical and guest-focused: read the room, keep service moving, and let the drink support conversation rather than overwhelm it. He values the chance to connect with strangers, learn from them, and, if nothing else, share a laugh.

In his hands, the bar is a place where a guest feels remembered, a mood is read correctly, and a martini arrives cold enough to make the room feel easier to enter. McGregor’s path began behind the bar at The Adelaide Oyster House in St. John’s, NL, where he learned the cadence of service through conversation, orders, guest comfort, and detail happening at once. He later bartended at Field Guide, where that early fluency developed into a sharper command of hospitality and drink.

Those rooms taught him that cocktail work is not only technical. A drink can carry place, a joke can change the temperature of a room, and a small act of attention can make a short visit matter. At Highwayman, his work is shaped by storytelling, sustainability, and community, with a specialty summed up plainly as Maritime hospitality, bad jokes, and ice cold martinis. The bar style is cocktail-forward but unpretentious, with ease treated as part of the build.

Technique is present, but not performed for its own sake. The aim is a room that feels welcoming, attentive, and rooted in place, where the guest remains the focus. His cocktails reflect that approach through clear, specific flavours. Highwayman’s Olive Leaf Martini is his take on 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 is smoky and savoury, designed to pair well with earthy, umami-rich dishes.

The Hodge Podge Flip shows his seasonal thinking, shifting toward fall with corn milk, carrots, and ginger. The Apple Butter Martini brings the same specificity, combining Tanqueray 10 Gin, Pineapple Weed Vermouth, and an Apple Butter Liqueur. His list of signature drinks also includes Crème Fraîche Vesper. Across these drinks, the emphasis stays close to memory, seasonality, and flavours that feel recognizable without being obvious.

McGregor’s perspective on taste is tied to seasonality and to the food of family life, with dishes that combine interesting flavours. That sensibility carries into his work at Highwayman, where the bar is defined by precision, character, and a clear sense of place. He builds drinks that are bracing, savoury, seasonal, and playful, but always anchored in hospitality that feels direct and human. His work is not about display. It is about making the exchange across the bar feel natural, memorable, and worth returning to.