Best Restaurants in Oakville and the Surrounding Area

Hey there! I’m Alida, a Registered Dietitian based in Ontario, Canada. I was raised around delicious food made with love and I am a huge believer in the connection that comes from being around a table together. While I now live in Milton, I grew up in Oakville and lived there until I left for university. Over the years I’ve had lots of opportunity to check out the local food scene and solidify my list of favourites, and I’m sharing my top picks for best restaurants in Oakville and the surrounding area with you!

Whether sharing food happens around the table in your home or in a cozy restaurant booth, there can be lots to look forward to (a night off from cooking and dishes, trying new foods), and maybe also a few things that can cause some stress … more on that later.

Before I begin, I want to address the privilege of affording to dine out at restaurants. I recognize that eating out is a luxury not everyone can afford and that eating out with any frequency as a part of an intuitive eating practice is a privilege for which I am grateful. 

Here is my list of some of the best Oakville eateries, as well as my go-to spots in Milton and Burlington.

Where to eat in Oakville, Ontario

Stoney’s Bread Company – Stoney’s has great quality and delicious food. It’s the perfect casual dining spot, offering soups, killer sandwiches, satisfying salads, pastas and pizzas. Everything tastes super fresh and is made to order. My menu favourites are the grilled chicken caesar salad (a classic, but this one is elevated with a smokey garlic dressing, and it’s served with grilled focaccia so you’re not missing out on carbs for balance and satisfaction) or the balsamic chicken sandwich.

Piano Piano – This spot has lovely indoor and outdoor space, at a great location right downtown. I recommend grabbing a meal or snack then exploring the shops nearby or taking a walk by the Oakville waterfront. They serve traditional Italian food, including handmade pasta. My winning lineup starts with the piano piano spritz (an aperol spritz with a peachy twist), then The Hot Rod pizza and ends with their amazing lemon cheesecake.

Colossus Greek Taverna – The decor here will transport you right to Greece! Colossus is a great spot if you’re in a food rut and need to try something new. I love sipping a red sangria while sharing appetizers of saganaki or the dip trio with warm pita and cucumber slices – I usually go for tzatziki, baba ganoush and hummus. For a main, I love the chicken souvlaki. 

Palermo Pub – THE place to go for wings.

Cupid’s Gourmet Bakery – It’s rare to find an entire bakery free of peanuts and tree nuts, but this one is committed to making the most delicious baked goods and making them safe for those with nut allergies – like me! My favourites are the vanilla bean cookie, black magic brownie and the cinnamon sour cream coffee cake. They’re so good I had them cater the desserts at my wedding!

a plate of food on a restaurant table

Best Restaurants in Burlington

Pearle’s Cafe – Pearle’s makes the best London fog tea latte – better than Starbucks in my opinion! I am always enchanted by their warm and friendly service, and the location is divine- right along the Burlington waterfront. It’s also one of my favourite spots to bring my laptop and get some work done when I need some inspiration and a change of scenery from my home office.

Burro – Burro offers super unique tacos with enough variety that everyone in your group can find something they’ll enjoy. It has a fun and edgy vibe. I recommend their spicy lychee lemonade while you snack on guacamole and chips. My go-to tacos are the habanero brisket, falafel, and fish. 

Barangas on the Beach – This spot has a one-of-a-kind location and a great opportunity to engage all your senses outside of just taste. It’s right on the beach and you will feel like you’ve been transported to the Bahamas! I usually go for an order of the olives & feta for an appetizer, followed by their grilled Atlantic salmon.

Best Restaurants in Milton

Sushi-Ya Japan – I go here for the small, intimate space and the family hospitality. I love to start with the edamame and vegetable spring rolls. If I’m feeling like rolls, I love doing a combo of the cucumber and avocado, the yam and avocado, or the salmon tempura roll. So yum!

Ivy Arms – The Ivy Arms gives you a classic pub atmosphere, and they have an awesome patio overlooking Main Street. When I’m feeling like wings but want to stay closer to home, I head to Ivy Arms. I would also recommend the California wrap and definitely get the fries, they are otherworldly.

How Eating Out Encourages Food Freedom and Helps You Practice Intuitive Eating

Social and spontaneous eating are two levels of my Nutrition Priority Pyramid, a tool I use with clients to help them build up their competence and confidence with intuitive eating. These both come into play while dining out. Eating at a restaurant can make you more aware of how your food rules and beliefs may be impacting your eating behaviours and your ability to enjoy spontaneous and social eating experiences. By following the framework provided by the Nutrition Priority Pyramid, you can learn that eating out doesn’t have to cause stress or anxiety, and it certainly does not have to turn into an out-of-control binge.

Spontaneous eating

Dining out helps you increase your flexibility with plans around food while maintaining trust in yourself to manage changes in your routine and environment in a way that is respectful of your body and its needs. Sometimes dining out happens without a lot of planning, or sometimes it’s planned but you make your decision about what to order spontaneously when the waiter arrives. Spontaneity might be just the thing you need more of if your eating habits are getting too repetitive, predictable, or controlled. If you’re looking for a fun challenge, try picking 2 options from the menu that you would be happy with, and ask your waiter to surprise you with one of them!

Social eating

Plate comparison and looking at calorie counts and other nutrition information posted on menus can be two common challenges with social eating. If restaurants, buffets, parties, and family meals fill you with dread (or maybe extreme excitement followed by crippling guilt), eating out can be great opportunity to practice your body attunement, emotional coping skills, and checking the facts when it comes to your food rules. With enough practice and the help of a challenge hierarchy, your confidence will grow and you’ll find yourself navigating social eating situations with a sense of freedom and ease. You’ll learn to make decisions around food that are rooted in self-care, enjoyment and connection instead of comparison and all-or-nothing thinking.

friends sharing a meal

Dining out reminds us of the connection, spontaneity and socialization that food brings

While eating out can be a fun experience, eating with others and eating foods prepared by others can add anxiety to the eating experience, especially when you struggle with disordered eating. If you want to learn more about these challenges and how to overcome them, check out this post. It also covers how dining out can be a valuable experience for growing in food freedom and building competence in intuitive eating, and I share my top tips for success when eating out.

If you’ve had a negative or antagonistic relationship with food in your past, dining out can be a way to re-discover the fun and playful sides of food. Whether trying a new cuisine or meeting friends at your long-time favourite place, you can use dining out as an opportunity to practice your intuitive eating principles and lean into food freedom. For more guidance on your journey towards being a competent intuitive eater, go grab my free guide which covers your First 3 Steps to Food Freedom. 

And if you live in or are visiting Oakville, I hope you get the chance to try someplace off my list of best restaurants in Oakville, Milton and Burlington! 

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from Guilt and Obsession
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of our getting started guide!
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