10 Fun and Local Things to Do Year-Round in Windsor Canada

Key Takeaways:

• Windsor blends riverside parks, cultural attractions, and scenic wineries into a year-round destination.

• The city offers everything from waterfront bike trails and casino nights to historic architecture and family fun.

• This guide highlights Windsor’s top experiences for every season and helps you discover free events on the fly.

Windsor, Ontario is often known as Canada’s southernmost city and for good reason — it enjoys one of the country’s mildest climates and a vibrant riverfront location. Sitting directly across from Detroit, Windsor has long been a city of connection, blending Canadian charm with a hint of American influence. It’s a place where you can stroll beside the Detroit River, sip local wine at lakeside vineyards, and explore history all within the same day. Whether you’re into food, festivals, nature, or nightlife, Windsor delivers a surprising mix of experiences year-round.

Table of Contents

1. Walk the Windsor Sculpture Park

2. Explore the Distinct Neighborhoods of Walkerville

3. Taste Local Wines on the Lake Erie North Shore

4. Experience the Action at Caesars Windsor

5. Bike the Ganatchio Trail

6. Tour the Canadian Aviation Museum

7. Attend the Windsor International Film Festival

8. Discover Dieppe Gardens and Peace Fountain

9. Step Back in Time at Willistead Manor

10. Join the Excitement of Art in the Park

1. Walk the Windsor Sculpture Park

One of Windsor’s most unique attractions is its riverfront Sculpture Park — a 5 km outdoor art trail featuring more than 30 large-scale installations. Located along the scenic Riverside Drive, the park showcases works from artists around the globe, making it feel like a contemporary gallery with a breeze. It’s the perfect spot for a casual stroll, a morning jog, or a sunset picnic with views of the Detroit skyline. Whether you’re an art lover or just appreciate creative spaces, this park brings beauty and inspiration to every season.

In the warmer months, flowers bloom along the path and cyclists glide past the sculptures on the adjacent bike lane. During the winter, the area is quieter but just as photogenic, especially after a fresh snowfall. The park is free, open 24/7, and suitable for all ages. Bring your camera, a coffee from a nearby café, and prepare for a surprisingly immersive outdoor art experience right in the heart of the city.

2. Explore the Distinct Neighborhoods of Walkerville

Walkerville is one of Windsor’s most charming historic neighborhoods, originally founded by Hiram Walker — the distiller behind Canadian Club whisky. Today, the district blends heritage architecture with trendy eateries, boutiques, and cultural stops. The streets are lined with red-brick buildings, vintage signs, and cozy pubs that retain the neighborhood’s industrial roots. It’s a great area to spend an afternoon wandering on foot and soaking in Windsor’s local character.

Don’t miss a visit to the Walkerville Brewery for a tour and a cold craft pint, or catch a live jazz set at a local bar. Bookshops, vintage clothing stores, and artisan coffee shops give the area a creative, indie vibe. Seasonal events like Walkerville Art Walk add even more energy, making it a local favorite year-round. Whether you’re visiting solo, on a date, or with friends, Walkerville blends old-world charm with modern flair effortlessly.

3. Taste Local Wines on the Lake Erie North Shore

Just a short drive from downtown Windsor lies the Lake Erie North Shore, a wine region known for its warm climate and fertile soil. Here you’ll find award-winning wineries offering tastings, vineyard tours, and seasonal events set against scenic countryside backdrops. Popular stops include Pelee Island Winery, Cooper’s Hawk Vineyards, and Viewpointe Estate, each with its own personality and offerings. It’s a relaxing, flavorful way to experience Windsor’s agricultural side.

In the summer, patios buzz with guests enjoying rosé and charcuterie boards overlooking the lake. In winter, cozy tasting rooms provide a warm refuge with mulled wine and food pairings. Most wineries are open year-round and offer rotating menus and events to match the seasons. Whether you’re a wine connoisseur or just curious, the Lake Erie North Shore is a memorable part of any Windsor trip.

4. Experience the Action at Caesars Windsor

For those seeking entertainment and nightlife, Caesars Windsor is a downtown staple offering casino games, concerts, and fine dining all under one roof. It’s one of the largest casinos in Canada and regularly hosts major acts, from comedy legends to live bands and international DJs. Beyond gaming, the resort features high-end restaurants, spa services, and riverfront views that make it feel like a full vacation experience. Open year-round, it’s a versatile option for rainy days or evening excitement.

Even if you don’t gamble, the on-site amenities and nightlife make it a lively hub to explore. Grab dinner at Neros Steakhouse or take in a show at The Colosseum, one of the city’s top performance venues. Located just steps from the waterfront, it’s also a convenient jumping-off point to explore downtown Windsor’s bars and lounges. Caesars offers big-city thrills with small-city ease.

5. Bike the Ganatchio Trail

If you’re a fan of cycling, walking, or inline skating, the Ganatchio Trail is a must. Stretching more than 8 km through Windsor’s eastern neighborhoods, this multi-use trail connects residential areas, parks, and nature reserves. It offers a peaceful ride or walk with views of lush trees, waterfront homes, and the occasional wildlife sighting. The trail is well-paved, family-friendly, and accessible year-round.

Along the way, you’ll find benches, scenic lookouts, and links to other trail systems like the Little River Corridor. Spring and fall are particularly beautiful times to ride, with blossoms and changing leaves framing the path. Local cyclists use the trail for everything from fitness training to relaxed weekend rides. Whether you’re renting a bike or bringing your own, this is one of Windsor’s top options for enjoying the outdoors without leaving town.

6. Tour the Canadian Aviation Museum

Located at the Windsor International Airport, the Canadian Aviation Museum is a hidden gem for history buffs and aviation fans. The museum houses an impressive collection of vintage aircraft, including military jets, trainers, and civilian planes, many of which are still in flying condition. Visitors can get up close to cockpits, propellers, and detailed exhibits that tell the story of Canada’s aviation milestones. It’s a hands-on experience with a knowledgeable staff that welcomes questions and conversation.

The museum also hosts flight simulations, educational workshops, and seasonal events, making it a great year-round indoor attraction. Kids especially love the interactive displays, and adults appreciate the level of detail and care put into preserving the planes. If you’re lucky, your visit might coincide with a special fly-in or restoration demonstration. It’s the kind of place that exceeds expectations and offers something new to learn at every turn.

7. Attend the Windsor International Film Festival

Film lovers visiting in the fall should make a point to attend the Windsor International Film Festival (WIFF), one of Canada’s top cultural events. Held annually in downtown Windsor, WIFF features independent films, documentaries, and international cinema across a wide range of genres. The event spans several venues, creating a buzzing arts atmosphere that transforms the city for a full week. With Q&A sessions, red carpet moments, and local filmmaker showcases, it’s a cinematic experience that rivals big-city festivals.

Tickets are affordable, and the event draws in both die-hard cinephiles and curious newcomers. Even outside of the main festival season, WIFF offers year-round programming and screenings at its home theater. Whether you’re into drama, comedy, or thought-provoking docs, the lineup always offers a fresh take on global storytelling. It’s a great way to experience Windsor’s arts scene in full motion.

8. Discover Dieppe Gardens and Peace Fountain

Dieppe Gardens is one of Windsor’s most picturesque spots, located along the waterfront and filled with manicured lawns, seasonal flowers, and memorial monuments. Visitors come here to walk the scenic paths, watch freighters glide by on the Detroit River, or simply relax with a coffee under a shade tree. It’s especially popular in summer when the Peace Fountain — the only international floating fountain in the world — is in full display, shooting water high into the air with colorful light shows at night.

The gardens also serve as a quiet reflection space, honoring veterans and promoting peaceful international relations. With benches overlooking the skyline and frequent community events nearby, it’s a place where locals and tourists alike gather to take in the view. Whether it’s sunrise or dusk, Dieppe Gardens delivers one of the most calming and beautiful experiences Windsor has to offer. Don’t forget your camera — the scenery is always Instagram-worthy.

9. Step Back in Time at Willistead Manor

Tucked inside the leafy Walkerville neighborhood, Willistead Manor is a stunning 36-room mansion built in 1906 that offers a glimpse into Windsor’s elegant past. Designed by famed architect Albert Kahn, the home blends Gothic and Tudor elements and was once owned by Edward Chandler Walker, son of Hiram Walker. Today, the manor serves as both a museum and event space, open for public tours during select times of the year. Visitors can walk through its grand halls, detailed woodwork, and period furnishings that paint a vivid picture of early 20th-century life.

The surrounding Willistead Park adds to the experience with towering trees, picnic spots, and community events like Art in the Park. In December, the mansion is decked out in holiday decorations for a magical seasonal tour. It’s a relaxing yet inspiring stop for those who appreciate architecture, history, or just a peaceful walk through one of Windsor’s most charming corners.

10. Join the Excitement of Art in the Park

Each June, Windsor’s Art in the Park festival takes over the grounds of Willistead Park with hundreds of artists, artisans, and performers from across the country. It’s one of Ontario’s largest outdoor art events and a beloved kickoff to the summer season. The atmosphere is lively, filled with music, food trucks, craft demonstrations, and pop-up tents showcasing everything from paintings to jewelry and woodwork. It’s a fantastic opportunity to support local creators while enjoying a festive day in a beautiful setting.

Even if you’re not in town for the main event, the area surrounding Willistead remains an art-lover’s favorite year-round, with galleries and artisan shops nearby. Art in the Park has a community spirit that makes everyone feel welcome — whether you’re browsing or buying. Come early to beat the crowds and stay late for live music and warm summer vibes. It’s a great way to experience Windsor’s creative heart in full bloom.

What to do if you have kids?

Windsor offers plenty of family-friendly fun to keep little ones entertained in every season. The Adventure Bay Family Water Park is a top indoor attraction with slides, wave pools, and splash zones perfect for burning energy on cold or rainy days. Families can also enjoy Ojibway Nature Centre, where kids can hike short trails, learn about local wildlife, and explore interactive exhibits. In warmer months, Riverside’s Pirate Ship Park and Jackson Park’s floral gardens are great for playtime and picnics. Windsor’s manageable size, easy layout, and welcoming community make it a stress-free choice for traveling with kids.

Where can I find free events in Windsor Canada taking place this weekend?

To find free events happening in Windsor this weekend — from riverfront concerts and outdoor yoga to artisan markets and community festivals — use https://planmyweekend.ai. This AI-powered tool curates real-time event listings based on your interests, giving you instant access to what’s happening without digging through outdated websites. Whether you’re looking for a family activity, a pop-up art fair, or live music under the stars, this site helps you discover it with ease. It’s the smartest way to plan a spontaneous and affordable weekend in Windsor.

Final thoughts

Windsor, Canada is a city full of surprises — balancing outdoor beauty, cultural depth, and a welcoming vibe that makes every visit memorable. From historic neighborhoods and riverside trails to vibrant festivals and cozy cafés, there’s something for every traveler here. With year-round activities, a relaxed pace, and easy access to nature and nightlife alike, Windsor proves it’s far more than just a border town. Whether you’re exploring for a day or staying for a week, you’ll find that Windsor has more to offer than meets the eye — and plenty of reasons to return.