What to do in Windsor: The Perfect Weekend in Windsor-Essex County

Hey there, weekend warriors!

Looking for a fun-filled getaway that offers a perfect mix of city excitement and country charm? Windsor-Essex County might just be your ideal destination! Located at the southernmost tip of Canada, next to Detroit (Michigan), this region offers everything from waterfront views and wine tours to casino thrills and incredible food scenes.

✨ Where to Stay:

• Caesars Windsor

• Best Western Plus Waterfront Hotel

• DoubleTree by Hilton Windsor Hotel & Suites

✨ Where to Eat:

• 🍕 Windsor-style pizza is a must-try (Armando’s is my favourite)

• 🐟 Fresh Lake Erie perch is a local specialty at many county restaurants

• 🍺Craft breweries like Walkerville Brewery offer tours and tastings

✨ Bringing your furry friend?

• 🍦Top Pet-Friendly Spots with your dog 

• 🐾 Dog parks in the city

Friday Evening: Welcome to Windsor

Start your weekend adventure in Windsor's downtown area:

• Check into your hotel – The downtown core offers several great options like Caesars Windsor Hotel or the Holiday Inn Express, putting you close to the action.

• Dinner with a view – Head to one of Windsor's riverfront restaurants like The Bistro at the River or Republik Asian Eatery and Bar. Enjoy your meal with stunning views of the Detroit skyline across the water.

• Evening entertainment options:

  • Try your luck at Caesars Windsor casino

  • Catch a show at the Chrysler Theatre

  • Explore the bars and pubs along Ouellette Avenue like Panache or The Loose Goose

  • Take a peaceful evening stroll along the Windsor Sculpture Park on the riverfront

Saturday Morning: City Explorations

Fuel up for a day of adventure:

• Breakfast in Walkerville – This charming historic neighbourhood is home to great breakfast spots like The Twisted Apron or Toast.

• Explore Walkerville's history – Take a morning walk through this neighbourhood built by whisky baron Hiram Walker. Don't miss:

  • Willistead Manor and park

  • Unique local shops and boutiques like Urban Art Market

Saturday Afternoon: Wine Country Tour

Time to head out to Essex County's beautiful wine region:

• Drive 35 minutes south to Essex County's Wine Route – with over 20 wineries in the region, you're in for a treat!

• Some must-visit wineries include:

  • Viewpointe Estate Winery (beautiful Lake Erie views)

  • Cooper's Hawk Vineyards (amazing VQA wines)

  • Oxley Estate Winery (great wine and the patio is vibey)

  • Pelee Island Winery (Ontario's oldest winery)

• Many wineries offer tours, tastings, and have on-site restaurants with locally-sourced menus.

• Pro tip: Consider booking a wine tour service so everyone can enjoy the tastings without worrying about driving!

Saturday Evening: Kingsville or Leamington

Spend your evening in one of Essex County's charming towns:

• Kingsville offers a picturesque downtown with excellent dining options like The Grove Brew House or Mettawas Station.

• Leamington also has great restaurants and a beautiful marina area perfect for sunset walks.

• Both towns offer a more relaxed pace compared to Windsor, with friendly locals and charming main streets.

Sunday Afternoon: Final Stops

Complete your weekend with these must-see attractions within a 30 minute drive from Windsor:

• Fort Malden National Historic Site in Amherstburg offers beautiful grounds along the Detroit River and important Canadian history.

• Historic Amherstburg is worth exploring with its charming shops and waterfront parks.

• Before heading home, stop at The Waterfront Ice Cream for a quick sweet treat with waterfront views.

Windsor-Essex is full of flavor, charm, and spots perfect for bonding over brunch. Whether you’re celebrating something special or just need a good catch-up session, these local gems set the scene for the perfect girls’ brunch.

What’s your go-to brunch spot?
Discover the Best Restaurants in Windsor and Essex County 

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Until next time..

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So, are you coming to Windsor or what? 🫡

- Eating Windsor Essex