Where to Eat & Drink in Windsor, Nova Scotia

Windsor is a small town about 40 minutes from Halifax in the Annapolis Valley of Nova Scotia, Canada. This little town has come a long way in the last ten years, and is now not only a spot young families choose to make home, but also a great destination for travelers. If you’ve come to Windsor, and perhaps are staying at my AirBnB, you’ve come to a great spot – especially if you’re keen on good food and fancy cocktails! So if you’re in town for a couple of days, here’s where to eat and drink in Windsor.

Drink: Cherry Tree Distillery

In a little historical house on Gerrish Street, Cherry Tree Distillery is a beautiful micro-distillery, with total speakeasy vibes. Jo and Dave serve up fancy cocktails – and mini taster cocktails! – with their own gin and vodka made in-house. Everything from the furnishings to the labels has been so tastefully considered, this is must-visit spot when you’re in Windsor.

163 Gerrish Street, Windsor | Open Thursday through Sunday

Eat and Drink in Windsor: Gerrish & Gray

Across the street from Cherry Tree is Gerrish & Grey, the newest and cutest coffee shop in Windsor. They do a great brunch – eggs benny, mac and cheese, French toast – and coffee and pastries all day. Even if you don’t do a whole meal, I definitely recommend having a coffee and a scone, and a seat in the window or by the fireplace.

134 Gerrish Street, Windsor | Open daily, 8:00-4:00

Looking for more things to do around Windsor? Check out Hants County

Eat: Walkers Restaurant

Just minutes on foot from my AirBnB is Walkers – a sweet little diner with helpful staff and a great breakfast menu. This is the only diner I’ve found that will bring me one poached egg and some buttered toast with no extras! Highly recommend for breakfast.

793 O’Brien Street, Windsor | Open daily, 7:00am-9:00pm

Eat & Drink: Bent Ridge Winery

Bent Ridge is in such a beautiful location, it’s worth going up just for the views. The food is delicious, and they do special grill nights for the carnivores who would like a freshly grilled steak. They have an Italian style menu, and the restaurant is set right on the vineyard. This is a bit out of town, so designate a driver in advance! Reservations are recommended for grill nights.

4499 Route 14, Windsor | Open daily, ~11:00am-7:00pm

Eat: Lisa’s Family Restaurant

A very popular, casual dining spot on the main street in Windsor, walkable from the house.

30 Water Street, Windsor | Open daily, 11:00am-7:00pm

Drink: Schoolhouse Brewery

Totally school themed! Head down for a drink, a flight, or a non-beer if that’s not your thing.

Eat: The Spitfire Arms

The Spitfire is true town pub. If you stay more than a couple of nights, you’re sure to run into someone you know!

29 Water Street, Windsor | Open daily, 11:00am – late

Eat: Hole in the Wall

Hole in the Wall is a very popular, slightly more upscale bistro-style restaurant, right next to the Spitfire. Reservations are recommended. They also do cool themed menus from around the world!

23 Water Street, Windsor | Open Wednesday – Sunday; see website for daily hours

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