Your Ultimate Summer Weekend Guide to Windsor Essex
Windsor Essex is one of those Ontario destinations that feels made for summer. Between the Lake Erie shoreline, local wineries, small-town food stops, national park adventures, island biking, and dark sky experiences, this region offers the perfect mix of outdoor adventure and slow summer travel.
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I spent a summer weekend exploring Leamington, Point Pelee, Pelee Island, and Windsor, and what surprised me most was how much variety you can fit into one trip. One day you are walking through wetlands and enjoying a local brewery, the next you are kayaking through Point Pelee, taking a ferry to Pelee Island, biking to wineries, and ending the weekend with a paddle and café in Windsor.
If you are looking for a summer getaway in Ontario that blends nature, food, wine, beaches, and adventure, here is how to spend a weekend in Windsor Essex.
A summer weekend in Windsor Essex is the perfect mix of beaches, paddling, wineries, island exploring, and local food.
Start Your Trip with Nature, Craft Beer & a Summer Market in Leamington
A great way to ease into the weekend is with a stop at Hillman Marsh Conservation Area. This peaceful conservation area is a beautiful place for a walk, especially if you enjoy birding, wetlands, photography, or simply starting a road trip with time outside. It is quiet, scenic, and gives you a sense of the natural landscapes that make this part of Ontario so special.
After spending some time outdoors, head into Leamington for dinner at Cured Craft Brewing Co. Located in the heart of uptown Leamington, this local craft brewery is a great first-night stop if you love casual food, small-batch beer, and a relaxed patio atmosphere.
If you are visiting on a summer Friday, make time for the Leamington Mill St. Market. The market brings together live music, local vendors, food, drinks, and a lively summer street festival feel. It is the kind of stop that makes a trip feel more local, especially if you enjoy wandering, snacking, and taking in the energy of a small town summer night.
For the weekend, I stayed at Best Western Plus Leamington, which made a convenient home base for exploring Leamington, Point Pelee National Park, local beaches, and nearby food stops. After long days outside, it was nice to have an easy place to return to that kept the itinerary simple and close to the main summer activities.
Start your Windsor Essex weekend with a nature walk at Hillman Marsh before heading into Leamington for local food, drinks, and summer market vibes.
Spend the Morning by the Water
The next morning, start slow with a walk along the Caldwell First Nation Conservation Boardwalk or Seacliff Beach. Both are great options if you want to enjoy the Lake Erie shoreline before the day gets busy.
The Caldwell Boardwalk offers a quiet and meaningful place to connect with the landscape, while Seacliff Beach gives you that classic summer feeling with wide beach views, fresh air, and space to enjoy the water. On a clear day, you may even be able to see Pelee Island in the distance.
For breakfast, stop at Green Heart Kitchen in Kingsville. It is a great option if you want something fresh before a full day of exploring. Think smoothies, bowls, baked goods, and wholesome meals made with local ingredients.
Before continuing the day, make a stop at Lee & Maria’s in Kingsville to pick up snacks, fresh produce, and local provisions for the road. It is the perfect kind of market stop before a full day of wineries, beaches, and exploring Point Pelee National Park.
Add a Winery Stop in Kingsville
No summer trip to Windsor Essex feels complete without visiting at least one winery. After breakfast, head to Mastronardi Estate Winery for a wine tasting.
The Windsor Essex wine region is such a big part of the area’s identity, and a winery stop adds a slower, more relaxed moment to the itinerary. It is also a nice contrast to the outdoor adventure side of the trip. You get to enjoy the rural scenery, try local wines, and experience a different side of the region before heading back toward Leamington.
A summer weekend in Windsor Essex pairs perfectly with a local winery stop in Kingsville.
Explore Point Pelee National Park by Land and Water
Before heading into Point Pelee National Park, stop at Oven 360 Leamington for an easy lunch. Their fresh, customizable pizzas are a great option before spending the afternoon hiking, paddling, or exploring the park. From there, make your way to Point Pelee National Park, one of the biggest highlights of the trip.
Point Pelee is the southernmost point of mainland Canada, but it is also one of those places where you can choose your own adventure. You can walk to the Tip, explore the marsh boardwalk, visit the lookout tower, stop by the Visitor Centre, or spend time paddling through the marsh.
For an outdoorsy summer experience, rent a kayak with Pelee Wings Outfitters and explore the park from the water. Paddling through the marsh gives you a totally different perspective of Point Pelee. It feels peaceful, immersive, and very connected to the wildlife and landscape around you.
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After a full afternoon in the park, head to Augusto’s Grill for dinner in Leamington. Then, if your timing lines up, return to Point Pelee for Dark Sky Nights. This is what made the day feel extra special. There are not many places where you can spend the afternoon kayaking through a national park and then return after sunset for stargazing.
As someone who loves both the outdoors and the night sky, this was one of my favourite parts of the trip.
Point Pelee National Park is a must-visit in summer, especially if you want to paddle, hike, explore the marsh, and stay after dark for stargazing.
Take the Ferry to Pelee Island
The next day, take the ferry from Leamington to Pelee Island. The ferry ride itself makes the day feel like a proper summer adventure. There is something about leaving the mainland behind that immediately slows the pace of the trip.
Once you arrive, pick up bike rentals from The Pelee Shop and spend the day exploring the island by bike. This is one of the best ways to experience Pelee Island because it gives you the freedom to stop wherever you want, take photos, visit nature areas, and enjoy the quiet island roads.
Start with lunch and a tasting at Pelee Island Winery Pavilion, then spend the afternoon visiting some of the island’s points of interest. Depending on your timing, you can explore places like Fish Point, Lighthouse Point, nature reserves, or historic sites like Vin Villa.
What I loved most about Pelee Island is that it does not feel rushed. It is the kind of place where the best part is simply biking, stopping for views, and letting the day unfold around the ferry schedule.
Click here to read a few tips and tricks and what you need to Know Before You Go to Pelee Island.
Pelee Island is one of the best summer day trips in Windsor Essex – rent a bike, visit the winery, and explore the island at your own pace.
End the Weekend with a Paddle or Ferry Ride to Peche Island
On the final morning, head into Windsor for one more outdoor adventure: Peche Island. Located just off the Detroit River shoreline, this 86-acre island offers a completely different feel from Point Pelee National Park and Pelee Island. It is close to the city, but once you are on the water or walking the island trails, it still feels like a quiet nature escape.
If you are paddling over on your own, launch from Kayak Cove Beach, which gives paddlers access toward Peche Island. Because you are crossing open water on the Detroit River, make sure to check the wind, current, and weather conditions before heading out. Wear a properly fitted PFD, bring water, and only paddle across if conditions are safe for your experience level.
For visitors who do not want to paddle, you can take the seasonal ferry/boat service to Peche Island from Lakeview Park Marina. This is a great option if you want to explore the island without bringing your own kayak, canoe, or paddleboard.
Once you arrive, take time to explore the island’s trails, shoreline views, canals, picnic areas, and natural spaces. Peche Island also has an interesting history. It was purchased by Hiram Walker in 1883 and used as his summer property, with buildings that once included a large home, stable, greenhouse, and icehouse. Today, the island is owned by the City of Windsor and is open seasonally for public use.
After a few days of beaches, wineries, national parks, and island exploring, Peche Island felt like a calm and scenic way to end the trip. After your paddle or ferry visit, stop at Taloola Café in Windsor for breakfast or brunch before heading home. It has that cozy neighbourhood café feel and makes a great final stop after a full Windsor Essex summer weekend.
End your Windsor Essex summer weekend with a paddle to Peche Island and a cozy café stop in Windsor.
For one last toast to the Windsor Essex region plan a visit to VIN Winery. One of the closest wineries to the City of Windsor and 1km off the Greenway Trail, their winemakers have set out to create wines that are drinkable, unique, balanced and distinctly local. With partner BREW microbrewery, their patio is a perfect way to end a summer night.
Why Windsor Essex Should Be on Your Summer List
What I loved most about this trip is how much variety Windsor Essex offers in just a few days. You can start your weekend walking through wetlands and enjoying a local brewery, spend the next day paddling through Point Pelee, take a ferry to Pelee Island, bike to wineries and nature reserves, and still finish with a peaceful paddle near Windsor.
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It is the kind of summer destination that works for outdoor lovers, foodies, couples, friend groups, and anyone looking for an Ontario getaway that feels a little different.
For me, Windsor Essex was the perfect reminder that you do not always have to travel far to find beaches, paddling, local food, island adventures, and unforgettable summer moments.
Original Blog post by Caroline El Khoury @caroline.elkhoury
