Couples Getaway In Essex County

By: Roxana Rangel from My Travelling Backpack

Looking for a romantic getaway for you and your significant other? Kingsville is only a ~45min drive out of Windsor and has everything you’re looking for to make an unforgettable weekend getaway for two. By the end of this blog post, you’ll have some ideas of what to do, where to eat and where to stay for your upcoming couples getaway in Kingsville, Ontario! Be sure to check out My Travelling Backpack’s blog or @mytravellingbackpack (Instagram page) for more Windsor-Essex adventures!

What to do in Kingsville?

Explore Main Street!

As soon as you enter Kingsville you will be greeted with the bustling Main St. There is everything from hotels, inns, restaurants, bakeries, breweries, coffee shops, and more! Take your time to explore and enjoy the county hospitality!  Kick off your evening strolling with your significant other hand in hand before you head to dinner, a wine tasting, or even a brewery flight experience!

Try some brews

Along Main St. you’ve got to experience these three local breweries – Kingsville Brew Tap House, Banded Goose Brewery, The Grove Brewery:

  • Kingsville Brew Tap HouseThis is a great place to bring your significant other to enjoy one (or a flight) of their handcrafted beers! I recommend couples to buy two flights (4×2) so you’re able to try all of the beers available on draft! If you’re looking for a quick bite they’ve also got a great appetizer selection, or if you are on the hungrier side you can choose from their full dinner menu! Before the summer ends, try their ‘Menu of Hope’ that has been connecting guests to the Canadian roots through the menu offering! A portion of every Menu of Hope is donated to the Terry Fox Foundation.
  • Banded Goose BreweryIf you’re staying at the Distinctive Inns of Kingsville, the Banded Goose Brewery is a great way to start or end your evening because the brewery is attached to the Inn — you don’t have to go too far! It has several beers on draft for your taste buds to enjoy!

PRO-TIP: If they have a nitro beer on tap, like their Nitro Sour, try it! It is so ‘bubbly smooth’ that it tastes like a kombucha!

  • The Grove Brewing CompanyIf you have the time, take a walk or a quick ~five min drive away from Main St, and you’ll find The Grove Brewery’s new location! Here you can find all of their beers on draft and if you fall in love with a particular beer, you can pick it up to take home from their in house Beer Fridge! While you’re there, be sure to try their tasty Beermosa during your visit — The Grove’s take on a classic mimosa’s — refreshing orange juice with their Paradise Lager!

 Taste award winning wine

Paglione Estate Winery (724 County Rd 50 E, Harrow ON) has a breathtaking location near Kingsville. As you drive onto the property, you are greeted with rows of vines that transport you all the way to Tuscany! They have a great food menu to select from for lunch or dinner (read about the food below), but you don’t want to miss their wine tasting! Their tasting flight costs $12 + tax and includes (4) 1 oz pours.

Currently on their tasting flight you could choose from any of these below.

 P.s. Some of these wines are now available at LCBO so you can enjoy them at your next Date Night in.

  • Josephine Sparkling
  • Pinot Grigio 2021
  • Riesling 2021
  • Chardonnay 2021
  • Rosé – Cabernet Sauvignon 2021
  • Santino Rosé 2021
  • Merlot 2019
  • Cabernet Merlot 2021
  • Cabernet Sauvignon 2021
  • Reserves – Gewürztaminer 2020
  • Reserves – Cabernet Franc 2020

Go for an Olive Oil + Vinegar tasting

You read that right! Experience an Olive Oil + Vinegar tasting at Cindy’s Home and Garden in their gourmet building Cindy’s Too.

They offer the biggest self-serve tester bar of vinegar and olive oil in Southwestern Ontario! They have unique olive oil flavours like Blood Orange, Chipotle, and Persian Limes or vinegar flavours like Mango, Coconut, and Cranberry Orange! This is a memorable and fun experience that you and your significant other can experience. When you’re there, ask for Michelle! She gives a wonderful explanation about the different olive oils and vinegars at Cindy’s and can even give you food pairing recommendations with the interesting flavours. After walking out of Cindy’s Too, ‘olive you’ will be saying I love you!

Shopping with a scoop

Go shopping for home goods and more with your significant other at Priscilla’s Presents! From the moment you step into the unique specialty shop, you are presented with a beautifully curated selection to shop for yourself or to gift to a special someone. There is everything from clothing, accessories, kitchen goods, wall decorations, and more! Once you’re done, choose between 36+ different flavours of ice cream from Here’s the Scoop — the ice cream shop next door — and explore the serene grounds of this location! Don’t forget to bring your camera and capture some photos for the memory books!

 Enjoy the summer breeze

Head to Cedar Beach Conservation Area (1031 Heritage Rd, N9Y 2E6, Kingsville ON) for some time in the sun (or shade)! Pack a lunch for two (or pick up lunch from Paglione Estate Winery), flip flops, beach towels, bathing suits, and sunscreen for a lovely afternoon. This popular spot is perfect for swimming, sunbathing, relaxing, and boat watching!

PRO-TIP: If you want to take refuge from the heat and sun, once you park the car, hang a left and head towards the creek (instead of the lake) when exiting the parking lot. It’s a wonderfully shaded area that is silent, romantic, and you can watch the water sports fans do their thing on the water.

Where to eat?

The Main Grill & Ale House (24 Main St W., N9Y 1H1, Kingsville ON)

Located in the heart of Kingsville, The Main Grill & Ale House is a dinner spot you don’t want to miss with your special someone. You can either sit on the patio and enjoy the bustling Main St., or dine inside at one of their cozy booths. Their take on elevated casual dining offers you a tasty menu with locally sourced, farm to table classics and regionally inspired dishes!  While you’re there try their house specials of the day — like the Fried Perch and Pickerel *chef kiss*, and if you can you have to try the Beef Medallions (pictured)! They are marinated in red wine, coated in a peppercorn rub and cooked to perfection — every bite was a joy. Reservations are highly recommended for the weekends! Be sure to call 519-733-8600 so you and your significant other can eat, drink, relax and enjoy!

Paglione Estate Winery (724 County Rd 50 E, Harrow ON)

When you’re at Paglione Estate Winery, pizza and wine is the answer! La Trattoria at Paglione Estate Winery has an amazing Italian selection of appetizers (L’Antipasti) from antipasto to calamari and even bacon wrapped chorizo dates! Once you’ve ordered some great apps, it’s pizze (pizza) time! Their pizzas are topped with the freshest ingredients, rolled out to a thin crust, and baked in a wood-fired oven. If you’re visiting on a Saturday or Sunday, be sure to grab a scoop (or a couple scoops) of Gelato! Reservations are recommended to dine here or you can order take out for a romantic picnic with pizza and wine for two!

The Grove Brewing Company (86 Wigle Ave, Unit 1, Kingsville ON)

After a romantic county evening, get the full Essex County wake up call by starting your day for breakfast at The Grove Brewing Company (The Grove for short)! They’ve got everything from a classic egg breakfast (pictured), omelets, french toast, eggs benny, and more! If you have coffee in the morning, you’ll be trying a local collaboration as their beans are from Red Lantern Coffee Co.! If you enjoy a mimosa in the morning, try their Beermosa! It is their Paradise Lager (also available in their Beer Fridge) with orange juice!

Note: If you’ve been to their previous location, or if this is your first time at the new location since they opened in June 2022 —  you will be blown away as soon as you walk through the door. This location now encompasses a restaurant, bar, brewery, warehouse, and a Beer Fridge to take home your favourite brews! Definitely stop by The Grove for the full Essex County sunrise experience!

 Where to stay?

Distinctive Inns of Kingsville

A couples getaway wouldn’t be complete without staying at the Distinctive Inns of Kingsville, located in the heart of Kingsville! It is an Inn that has a collection of unique rooms for every taste and adventurers! They provide a very convenient virtual concierge service that allows you to check in and communicate with their front desk with any questions or request for your stay. Once you get to the Inn, all you have to do is follow the check-in instructions and go to your room directly! On a personal note, we were blown away once we opened the door because the ensuite room (Room 14) had everything we needed! It had a great view onto Kingsville’s Main Street, it was decorated with the coolest furniture like bike gear lamps (pictured on either side of the bed), a beer door, etc,  and it was even equipped with locally sourced snacks for those late night cravings!

Check out their website to book your upcoming weekend getaway!


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How cute is this little guy? 🐐 Stop by @muscederevineyards to pay him a visit while you sip on their flavourful wine and try their famous pizza. #YQG #WindsorEssex #DiscoverOn #DiscoverCanada #DiscoverYQG #OntSouthwest ...

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