windsor ontario

How to spend 36 hours in Windsor Ontario

Windsor is quickly becoming a cultural hub of southwest Ontario and a great place for a weekend getaway. 

While it may be known for bordering the U.S. and providing visitors and locals with an amazing view of the Detroit skyline, Windsor has much more than its ‘Border City’ name suggests.

Celebrated chefs have been opening new restaurants, new breweries have been popping up trendy neighbourhoods, and there's an amazing selection of locally-owned boutiques and storefronts on its main streets.

Fall is a great times to check out Windsor’s farmers' markets, cafes, stores and parks. The city is easily accessible on foot, bicycle or via public transit.

Here's how to spend 36 hours in Windsor.

9 a.m. - Start your day at the Downtown Windsor Farmers Market

Pelissier Street is quickly becoming Windsor's hub for shopping and dining and has recently become the home of the Downtown Windsor Farmers Market.

The market hosts vendors from all over the county and includes bakers, local coffee maker Chance Coffee, fashion designers, produce and plants, local honey and much more.

If you’d like to explore Windsor by bike, Bike Windsor Essex provides free bike parking at the market — or rent a bike from them.

Make sure you don’t fill up on your market haul just yet. Cafe March 21st is a cute new addition to the downtown Windsor coffee scene. Grab a specialty latte, light breakfast or their amazing matcha cookies - plus they also have amazing ramen.

Before you leave downtown, take a trip to Edde’s Graffiti Alley. This art walk borders the market and features works from artists known around the world.

11 a.m. - Head east to Historic Olde Walkerville

The neighbourhood of Olde Walkerville was founded by Hiram Walker, the famous producer of Canadian Club Whisky. Originally its own town, Walkerville is still home to the Hiram Walker & Sons Distillery  and many historical hotspots.

To get to Walkerville you can take a 30-45 minute walk along Windsor’s Sculpture Park and take in the beautiful view of the Detroit skyline. You can also take the trip by Windsor Transit bus.

Walkerville is also home to Windsor’s best selection of vintage and boutique stores. Full Circle Vintage is a carefully curated collection of vintage clothing and accessories from over the decades. Full Circle has just opened a thrift section full of treasures and great finds.

For the lit fans out there, Biblioasis houses its own literary press and is a trendy bookstore. Filled with a ton of indie titles and curiosities, the employees are always ready to make suggestions or talk about the latest releases from the press.

Finish your shopping trip off at Jones & Co. Jones is known for carrying high-end vintage pieces and now have expanded to carry specialty gift items and trendy home decor.

1 p.m. - Check out Ford City and The Grand Cantina for lunch

Ford City was originally built as a community just for the Ford Motor Company and its factories. Steeped in Windsor’s rich automotive and industrial history, Ford City is now re-emerging as a cultural hub.

The Grand Cantina is a colourful and bustling stop for Mexican cuisine and great cocktails. They have a variety of dishes including vegetarian, vegan and gluten-free options. They also have a great back patio that hosts live music and DJs.

Before leaving Ford City, make sure to take a peek into Michael Difazio Reclaim Artistry to see amazing reclaimed wood furniture or Pressure Drop for some locally designed clothing and gifts.

3 p.m. - Check-in to a stylish Olde Walkerville boutique Airbnb

One of Windsor's top hotels, the Caesars Windsor Hotel and Casino, closed temporarily due to the pandemic. But there are plenty of Airbnb options such as the boutique suite in a restored historic Walkerville home.

5 p.m. - Take a stroll through Willistead Park

Grab a coffee at Anchor or a brew from Walkerville Brewery and then head to the beautiful Willistead Park, hidden behind bustling Wyandotte Street.

On the walk, be sure to see Willistead Manor (note tours are currently not running due to COVID-19), which was designed by renowned architect Albert Kahn.

The most famous Kahn structures can be found in Detroit but bits and pieces are scattered around the Walkerville neighbourhood, such as the beautiful red brick row houses Walker commissioned for his employees. 

6 p.m. - Indulge at Ortona 1864 Café & Panino Shop Ltd.

Just around the corner from your Airbnb, Ortona Café is Walkerville’s newest dining spot. Ortona looks like a bistro you would find in Paris and serves savory dishes like gnocchi poutine, a wide array of specialty cocktails and a great cup of espresso.

9 p.m. - See live music the Windsor-famous Phog Lounge

Phog was once voted the best live music venue in Canada by CBC Radio 3. Phog has hosted the likes of Rural Alberta Advantage, Yukon Blonde, Cadence Weapon and Leif Vollebekk.

Phog may look tiny from the outside, but it packs a ton of sound. While they have just re-opened their indoor stage, their new outdoor patio also features live jazz.

Phog can fill up quickly so if you can’t snag a spot, head to their sister site, Meteor. Right across University Avenue from Phog, Meteor's outdoor patio is nestled in Windsor’s newest graffiti collection, WIFF Alley — a homage to the Windsor International Film Festival.

11 p.m. - Have a nightcap at Maiden Lane Wine & Spirits

Maiden Lane is Windsor’s sleek new cocktail spot. Their menu has been carefully curated to feature ingredients not found on every bar shelf and are sure to spark something new for your palate. They also have a menu filled with international flavours and small plates.

11 a.m. - Wake up to a delectable breakfast at Twisted Apron

The Twisted Apron is known for its indulgent dishes and there is definitely something for the sweet or the savory food lover. Twisted adds gourmet touches to classic dishes and definitely come hungry.

1 p.m. - Paddle away with Urban Surf Co.

Explore beautiful Lake St. Clair and gorgeous views of Michigan with Urban Surf Co. Paddle around the abandoned Peche Island or get as close as you can to Detroit without crossing the border. Note reservations are required for this adventure.

5 p.m. - Pick up some Plant Joy donuts for your friends back home

Plant Joy is a haven for donut lovers and the best part — they’re vegan. These plant based donuts will be sure to take you on the best sugar trip of your life. Just try not to eat them all before you leave.

Make room for dinner by taking a stroll to Coventry Gardens park and see one last view of the beautiful riverfront.

7 p.m. - Visit the.dotte for a uniquely Windsor and Canadian experience

When entering the.dotte - pay close attention to its architecture. The owners transformed a Tim Horton’s into a chic new cocktail spot and small plates dining experience.

Enjoy a massive Caesar with some truffle fries and take in the charming neighbourhood of Riverside.

Lead photo by

Hermes Rivera. Writing by Alexandra Sellick.

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