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Oshawa Itineraries: Digital Nomad Edition

Welcome to the world of digital nomadism, where your office could be just as sandy as it is savvy! This lifestyle trend has taken over the tourism industry as it combines the freedom of travel with the necessity of work (thanks to the wonders of modern technology). More and more wanderlusters are trading in their traditional desks for destinations that inspire both productivity and adventure. Ready to join the movement? Let’s dive into your playful guide to working remotely from Oshawa! Here, we'll explore how Oshawa blends the best of both worlds—boosting your workday with a dash of fun and exploration. Pack your laptop and your sense of adventure; Oshawa awaits!

Day 1: Settle In and Explore 

Cork & Bean Oshawa
Start your day with a jolt of java from Cork & Bean.

GET TO WORK: Start your day with a hearty breakfast at Cork & Bean, a cozy café known for its delicious coffee and pastries. This also doubles as a great location to work or relax while enjoying the lovely ambiance. If you like it, you can stay all day as they also offer wine, craft beer and, depending on the day, live entertainment. Make sure to visit their website to see their daily special offers.

Stretch your legs while taking in the latest exhibit at the Robert McLaughlin Gallery.

BREAK TIME: Take a break from staring at your laptop screen and stroll through downtown Oshawa to the Robert McLaughlin Gallery (RMG). Admire the vast Canadian art collection in their modern and contemporary gallery space.

Your visit to Oshawa isn't complete without a slice of Teddy's Restaurant's famous Strawberry Pie!

HUNGRY: Continue West on King St. and head over to Teddy’s Restaurant and Deli. This Oshawa staple has been serving homestyle meals to the community for over forty years. Teddy's is known for its homemade dinners and delectable desserts, and its wide menu selection will meet any of your cravings. My personal favourite is Teddy’s burger with a side salad and their incredible house dressing - Oh, be sure to save room for a slice of strawberry pie (trust me!).

AFTERNOON FOCUS TIME: With a full belly, it's time to get back to work! Luckily, Oshawa has several co-working locations that offer quiet space, caffeine, and Wi-Fi and are available for rent by the day.

Head to Berry Hill Food Co. to try the BH Burger.

THE DINNER BELLS ARE RINGING: Whether meeting with colleagues or flying solo, treat yourself to dinner at another signature Oshawa restaurant. Berry Hill Food and Co. is known for its locally sourced ingredients and cozy atmosphere. The menu boasts flavourfully inspired soups and salads, cast iron brie, duck wings, (the mouthwatering) BH Burger and a variety of pizzas.

A butterfly's eye view of the Rossland Road Butterfly Garden.

GET SOME FRESH AIR: Clear your head after a day's work while breathing in some fresh air and getting a bit of exercise. Head over to the Rossland Road Butterfly Garden, where you can wander through the scenic grounds while searching for different species of butterflies.

Catch a live show at one of Oshawa's many music destinations.

STILL HAVE SOME ENERGY? End your day with a live performance at the iconic Biltmore Theatre, one of Oshawa's premier live music venues. Be sure to check the theatre’s schedule to see what's on!

Day 2: Work and Play

Enjoy a hearty breakfast at the Rainbow Restaurant.

FUEL UP: Breakfast is served (or will be) at one of Oshawa's top diners, the Rainbow Restaurant. Well-known for its traditional breakfasts and lunches, its wide range of offerings will satisfy even the heartiest appetites.


On your next work break, might we suggest a visit to the Ontario Regiment Museum? It has Canada's greatest functioning collection of vintage military vehicles. The museum's area of expertise is providing immersive historical encounters. Visitors may watch as several of the museum's vehicles fire up and enter the tank arena during events.

The Ontario Regiment RCAC Museum Tank
The Ontario Regiment RCAC Museum has A LOT of tanks on display


For a productivity boost, take a trip to Ave Coffee Co, which is for coffee lovers, environmentalists, and humanitarians. They only use high-quality coffee grown without pesticides or chemical fertilizers, using methods that protect bird habitats. Enjoy good quality coffee and get some work done. 


Have a lovely outdoor adventure and spend the afternoon hiking or biking along the trails at Harmony Creek Conservation Area.

Riley's Oshawa Interior
Riley's Oshawa is a comfortable spot for any social occasion.


Indulge in a pub dining experience and have dinner at Riley’s Pub, regarded as one of the top dining choices in Oshawa year after year. There is a large menu selection with large portions for you to enjoy (without breaking the bank!).


Wrap up the day and spend your evening at Club 717, the longest-running LGBTQIA+ space in the Durham Region. This buzzing nightclub serves great cocktails, live music, and karaoke and features Drag shows every Friday Night.

Day 3: Explore Nature and Local Culture 

Savour a leisurely breakfast at Kings Breakfast Place, where you'll find a wide variety of menu items at affordable prices, along with generous serving sizes that will satisfy your appetite. From eggs benedict to omelettes, different choices of scramble, waffles, and pancakes, just to name a few, there is something for every type of breakfast craving. 

Take a stroll through the gardens at Parkwood Estate.


Take part in a cultural experience and learn a little bit more about Oshawa's heritage. Visit the Parkwood Estate, the former home of the McLaughlin Family. Take a guided tour to learn about its history and explore the stunning gardens. Fun fact: Many movies, such as Billy Madison, were filmed at the Parkwood Estate. 

Pizza Munno Pizza
We interrupt your scrolling to bring you a picture of one of Pizza Munno's delicious offerings


For lunch grab a pizza to go from Pizza Munno’s an authentic Italian pizza experience. They offer a variety of pizzas, calzones and vegetarian options. Enjoy it in the restaurant or, head over to Lakeview Park for a scenic picnic lunch!


End off your afternoon with some retail therapy at the Oshawa Centre, the largest shopping mall in the Durham Region. With over 230 retail shops to wander, you may want to plan at least an hour.

Dinner at Shrimp Cocktail Oshawa
Hungry after a long day? Enjoy an upscale dining experience at Oshawa's Shrimp Cocktail.


Conclude your trip with a memorable dinner at Shrimp Cocktail. This refined dining experience is celebrated for its exquisite seafood creations and impeccable service. With a menu showcasing the freshest seafood, a curated wine list, and expertly crafted cocktails, guests are treated to a culinary journey of unparalleled quality. 

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