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Favorite Fall Festivals in Windsor-Essex
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Jilda Rose

  • August 22, 2024
  • 4 minutes read

Favorite Fall Festivals in Windsor-Essex

As the leaves turn and the air gets crisp, Windsor-Essex comes alive with a series of favorite fall festivals that showcase the region’s charm, tradition, and community spirit. Whether you’re a fan of rural fairs, art markets, or Halloween festivities, there’s something for everyone to enjoy during the autumn season.

September 2024: Harrow Fair, Grape Fest, Corn Fest and More

The Harrow Fair

One of the top picks for early fall is the Harrow Fair, running from August 29th to September 1st, 2024. With over 160 years of history, this event is a true celebration of rural Ontario, featuring livestock shows, home craft competitions, and a lively midway. The Harrow Fair offers an authentic rural experience and is ideal for families looking to immerse themselves in traditional country charm. Can’t-miss events include Rooster and People Crowing contests, the Pie Auction, Bossy Bingo, and Live Entertainment on the main stage.

The Harrow Fair Pie Auction
The Harrow Fair Pie Auction raised $82,000 in 2023.

Caboto Club Grape Festival

For live music, a Bocce Ball tournament, a spaghetti eating contest, and a grape stomping contest you’ll find everything important in Italian culture at Grape Fest by the Caboto Club on September 13-15th. Tickets are available through eventbrite.

Tecumseh Corn Festival

September also brings the Tecumseh Corn Festival on September 21st, 2024. This festival is a favorite for families and foodies alike, featuring a variety of corn-themed activities, live entertainment, and carnival fun. The festival is a perfect blend of food, music, and family-friendly fun, making it a must-attend event in the fall calendar.

The Ruthven Apple Festival

Ruthven Apple Festival tote featuring festival beneficiary Community Living Essex County.

The Ruthven Apple Festival, held on September 28th and 29th, 2024 at Colasanti’s Tropical Gardens, is a delightful celebration of all things apple! This festival offers a charming array of apple-themed activities and treats. Visitors can enjoy a variety of attractions, including apple picking, fresh apple cider, and homemade apple pies. The festival also features craft vendors, live entertainment, and fun family activities, making it a perfect outing for all ages. On top of providing fun fall festivities, Ruthven Apple Festival has raised over one million dollars in support of Community Living Essex County, with proceeds earmarked each year for the ongoing maintenance and purchase of wheelchair-accessible vehicles. With its focus on local produce and community spirit, the Ruthven Apple Festival is a sweet and enjoyable way to embrace the flavors of fall.

Amherstburg Uncommon Festival

Amherstburg Uncommon Festival is a standout event in the fall lineup, taking place on September 28th and 29th, 2024. This vibrant festival is a celebration of creativity and community, showcasing an eclectic mix of local art, music, and culture in the charming town of Amherstburg. The festival features a range of activities, including a unique artisan market where visitors can explore handcrafted goods and one-of-a-kind creations from talented local artists. Attendees can enjoy live music performances, street entertainment, and interactive art installations, all set against the picturesque backdrop of Amherstburg’s historic streets. The festival encourages you to ‘Dress up in your favorite wizardry or steampunk cosplay costume and join us for a weekend filled with fun. Expect more buskers, live performances, games, vendors & downtown businesses open to serve you, and wackier – than – ever fun-filled days. You will want to return every single day so you don’t miss a thing!‘

Amherstburg Uncommon Festival is among the top favorite for fall festival goers.

October 2024: Kingsville Migration Festival, Klite Festival, and More

Kingsville Migration Festival

October kicks off with the Kingsville Migration Festival from October 19th to 22nd, 2024. As one of the most beloved fall events, this festival celebrates the annual migration with activities like a parade, free community bike tours, a bustling marketplace, and an en Plein air painting competition called The Great Migration Paint Out. It’s a wonderful way to connect with nature and enjoy a festive atmosphere in the charming town of Kingsville.

Klite Festival

Enjoy two days of amazing kite performances, more attractions, and incredible kites on October 5th and 6th from 10 am – 3 pm and the Leamington SC Soccer Fields. Stay tuned to their Facebook page for more details!

Art at the oTENTicks

Art at the oTENTiks is a two-day event from October 19-20th, featuring artists and artisans demonstrating their craft and selling their goods. Admission to the event for the general public is included with park admission. Artists have the option to be “in-residence” in an oTENTik site or set up a tent in the marketplace space. Enjoy the diverse natural beauty of Point Pelee National Park and meet the artisans inspired by Mother Earth.

movie theatre seats

Windsor International Film Festival

WIFF runs from October 24th – November 3rd with the ability to purchase a festival pass and nestle yourself in a plushy theater seat all weekend, as well as be selective in your viewing with single ticket purchases. Check back in with their website for updates on the film screening schedule.

These favorite fall festivals in Windsor-Essex offer something for everyone, from the rural charm of the Harrow Fair to the unique draw of the Amherstburg Uncommon. Each event provides a different opportunity to experience the culture, traditions, and community spirit of the region. For more details on these and other favorite fall festivals, be sure to visit the Windsor-Essex events page. Looking for accommodations for one of these perfect fall weekend events? For premier vacation home rentals nearby visit Dream Hospitality Travel Services Ltd. and discover comfort like home.

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