What You Won’t Find in a Brochure

 

While brochures highlight the iconic sights and top attractions of Windsor-Essex, there’s a whole other side of this vibrant region that only locals truly know. Whether you’re moving here or just exploring deeper, this insider’s guide reveals the real Windsor-Essex — the places, people, and experiences that make it truly special.

Festivals and Open-Air Events in Windsor-Essex

 

Harrow Fair

A beloved tradition since 1854, the Harrow Fair is one of the oldest community fairs in Ontario and a must-experience event in Essex County. Held every Labour Day weekend, it features agricultural exhibits, livestock shows, homecraft competitions, a midway, live music, and delicious fair food. The Harrow Fair blends small-town charm with big fun, showcasing the region’s deep farming roots and sense of community spirit. HarrowFair.com

Amherstburg Open Air Weekends

From May 30 to August 31, 2025, Amherstburg’s charming downtown closes to traffic every weekend for Amherstburg Open Air Weekends. Think open patios, live music, yoga in the park, historic walking tours, and a family-friendly vibe. New for 2025: weekly Friday night markets and guided historic tours. Visit Amherstburg

Tecumseh Corn Festival

A long-standing tradition, the Tecumseh Corn Festival brings the community together with live entertainment, a midway, food vendors, and plenty of fresh local corn. It’s summer fun at its best. Windsorite.ca

Kingsville Migration Festival

This unique festival celebrates the town’s natural heritage, particularly the migration of birds and monarch butterflies. Expect local crafts, educational programming, live music, and food vendors throughout the weekend. Kingsville.ca

LaSalle Strawberry Festival

Held each June, the LaSalle Strawberry Festival offers something for all ages, including carnival rides, live music, a parade, and lots of strawberry-inspired treats. LaSalle.ca

 

Active Living and Recreation

 

Walking Tours

• Walkerville Walking Tour: Discover the legacy of Hiram Walker and the roots of Canadian Club Whisky, with historic architecture and local lore. VisitWindsorEssex.com
• Victoria Avenue Walking Tour: Stroll along Windsor’s elegant, historic residential avenue with homes showcasing architectural styles from across the decades. City of Windsor

Trails

• Riverfront Trail: A scenic, paved trail running along Windsor’s waterfront, perfect for walking, biking, and admiring public art at the Windsor Sculpture Park. VisitWindsorEssex.com
• Chrysler Canada Greenway: A 42 km trail connecting Windsor to Leamington, passing through fields, forests, and small towns. Ideal for cyclists and nature lovers. Wikipedia

Nature Preserves & Hidden Gems

• Point Pelee National Park: Located at the southernmost point of mainland Canada, Point Pelee is a year-round destination for birdwatchers, cyclists, and nature lovers. With boardwalks over marshlands, forest trails, and sandy beaches, it’s an immersive experience in biodiversity. It’s also world-renowned for spring and fall bird migrations. (Parks Canada)
• Ojibway Prairie Complex: One of Canada’s most endangered ecosystems, this 350-hectare sanctuary includes rare tallgrass prairie and over 160 species-at-risk. Wikipedia
• Black Oak Heritage Park: A quiet, forested area next to Ojibway offering walking trails and prime bird-watching spots. Wikipedia

Local Sports and Events

 

Windsor-Essex is proud of its local sports culture:

• Windsor Spitfires (OHL hockey)
• Windsor Express (NBL Canada basketball)
• ActiveCity.ca helps residents find leagues, recreational programs, and fitness classes across the region.

Boutique Living: Cafes, Shops, and Eats

 

Windsor-Essex thrives on its indie spirit and small business love:

• Maiden Lane (Downtown Windsor): A cozy laneway filled with local boutiques, murals, live music, and cafes.
• Windsor Essex Coffee Trail: A curated tour of independent coffee shops from Amherstburg to Kingsville. VisitWindsorEssex.com
• The Cook’s Shop: One of Windsor’s most iconic Italian restaurants, cherished by locals.
• Historic Downtown Amherstburg:  Lined with unique shops and eateries.

On the Water: Boat Tours & Island Escapes

 

• Windsor Premier Cruises: Offers scenic and dinner cruises along the Detroit River with incredible skyline views. WindsorPremierCruises.com
• Peche Island Tours: Hop on a city-run boat tour to Peche Island and explore this historic natural gem via a short, guided adventure. City of Windsor
• Pelee Island Adventures: Venture a little further with a ferry ride to Pelee Island, Ontario’s southernmost inhabited point. Known for its tranquil beaches, winery, cycling routes, and birdwatching, it’s the perfect weekend escape for nature lovers and explorers alike. VisitPeleeIsland.com

Farmers’ Markets & Local Produce

 

Windsor-Essex is home to a vibrant collection of farmers’ markets that celebrate local growers and fresh seasonal produce. Whether you’re picking up sun-ripened tomatoes in Leamington, artisan bread in Kingsville, or fresh-cut flowers in Amherstburg, each market reflects the unique agricultural richness of the area. The Downtown Windsor Farmers’ Market runs weekly from spring to fall, showcasing everything from organic veggies to handmade preserves. Other notable stops include the Amherstburg Farmers’ Market, and the Leamington Farmers’ Market, one of Ontario’s longest-running. These markets offer more than just food—they’re community hubs where locals connect, musicians perform, and the region’s farm-to-table culture shines. VisitWindsorEssex.com

 

Final Thoughts

 

Living in Windsor-Essex means more than just affordable homes and lake views (though we love those too). It’s about walking where history was made, biking where the prairies bloom, dining where recipes are passed down generations, and dancing in the streets on a Friday night in Amherstburg.

At The Dan Gemus Real Estate Team, we don’t just sell homes in Windsor and Essex County—we live here, we work here, we explore here, and we love sharing the hidden magic of our region with newcomers. Whether you’re relocating, downsizing, or just ready for a fresh chapter, we’re here to help you find your perfect place in this one-of-a-kind community.  Ready to explore Windsor-Essex like a local?  Contact The Dan Gemus Real Estate Team today to get started.