Fall Activities in Windsor Essex

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Fall Activities in Windsor Essex are your golden ticket to crisp air, cozy fun, and budget-friendly magic in southwestern Ontario. Fall Activities in Windsor Essex are vibrant, full of charm, and perfect for families, seniors, and fun-seekers alike. Ready to fall in love with autumn? Here’s a fall activities list that will spark your curiosity, warm your heart, and get you planning your next getaway.

Updated for 2025

Why Fall Activities in Windsor Essex Should Be on Your Radar

Fall Activities in Windsor Essex are truly special. The summer crowds ease, the temperatures cool, and the whole county bursts into color. You’ll find yourself walking under golden canopies, sipping fresh cider, and maybe even catching a Caesars Windsor show.

Unlike bigger cities, Windsor Essex offers affordable accommodations and less traffic. That means you can spend more on what really matters—treating yourself, spoiling the grandkids, or grabbing an extra pumpkin spice latte or two. And with so many autumn activities Ontario is known for happening right here, you won’t run out of things to do./*! elementor – v3.17.0 – 08-11-2023 */<br /><br>.elementor-column .elementor-spacer-inner{height:var(–spacer-size)}.e-con{–container-widget-width:100%}.e-con-inner>.elementor-widget-spacer,.e-con>.elementor-widget-spacer{width:var(–container-widget-width,var(–spacer-size));–align-self:var(–container-widget-align-self,initial);–flex-shrink:0}.e-con-inner>.elementor-widget-spacer>.elementor-widget-container,.e-con>.elementor-widget-spacer>.elementor-widget-container{height:100%;width:100%}.e-con-inner>.elementor-widget-spacer>.elementor-widget-container>.elementor-spacer,.e-con>.elementor-widget-spacer>.elementor-widget-container>.elementor-spacer{height:100%}.e-con-inner>.elementor-widget-spacer>.elementor-widget-container>.elementor-spacer>.elementor-spacer-inner,.e-con>.elementor-widget-spacer>.elementor-widget-container>.elementor-spacer>.elementor-spacer-inner{height:var(–container-widget-height,var(–spacer-size))}.e-con-inner>.elementor-widget-spacer.elementor-widget-empty,.e-con>.elementor-widget-spacer.elementor-widget-empty{position:relative;min-height:22px;min-width:22px}.e-con-inner>.elementor-widget-spacer.elementor-widget-empty .elementor-widget-empty-icon,.e-con>.elementor-widget-spacer.elementor-widget-empty .elementor-widget-empty-icon{position:absolute;top:0;bottom:0;left:0;right:0;margin:auto;padding:0;width:22px;height:22px}

How to get to Windsor Essex

Located in southwestern-most area of Ontario, Canada, Windsor and the surrounding county of Essex is easily accessible by planes, trains and automobiles.

By Airplane

Windsor International Airport has regular flights from most major Canadian cities and is serviced by Air Canada, West Jet, Porter, Flair, and Sunwing.  Check here for flights to and from Windsor.

By Train

If you have read any of my other posts, you will already know that the train is my favourite mode of inter-city travel.  Via Rail Canada has two to three trips to and from Windsor daily, depending on the time of year.  Check here for Via Rail Tickets. 

By Automobile

Car rental kiosks are available at both the train station and the airport.  Check here for available car rentals.  If you are driving your own car, I would like to recommend that you get off Highway 401 (the major freeway connecting Toronto to Windsor) unless time is an issue. Try some of the more scenic routes. 

Highway 3 runs along the north shore of Lake Erie through small towns and villages.  You will also pass through farms and orchards that are all very picture-worthy.  Another route would be along Highway 2, which runs a little north of the 401 and through the city of London.

Map of Southwestern Ontario

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Windsor Essex Places to Stay

If you are a bird watcher, you are going to want to stay in the Leamington area, relatively close to Hillman Marsh and Point Pelee National Park. 

I am going to recommend two hotels at which I have recently stayed.  The first is the Comfort Inn on Erie Street South in Leamington.  Its major advantage is that it is in town.  It is a short walk or taxi ride to shopping and restaurants (if you don’t have a car). 

My second recommendation will be the Best Western on Bevel Road.  To those of us boomers who grew up in the area may be remembered as the Pelee Motor Inn.  It was one of the first larger hotels to spring up in the area.  It has all the amenities that you could want – fitness, pool, recreation area.  It is a short drive to Point Pelee.  It also has one of the best breakfasts for your buck that I have found in a hotel recently.

In Windsor proper, you will find all of the major hotel/motel brands.  I have recently stayed at the Four Points by Sheraton and the Caesar’s Hotel Windsor.  Depending on your tastes, I would recommend a spot close to the downtown core and close to the riverfront walk.  

Check here for hotel, motel and BnB rentals.

Updated Fall Activities List for 2025

Here’s a fresh round-up of autumn fun in the Windsor Essex area. Whether you’re looking for fun family fall activities, a relaxing outing for grandparents, or unique events, there’s plenty to choose from.

Fall Festivals and Events in Windsor Essex

The Windsor Essex region comes alive with fall festivals. Here are some 2025 highlights:

• LaSalle Autumn Market (Sept 5–7, 2025)
  Browse handmade crafts, seasonal eats, and live music at the LaSalle Event Centre. A great way to support local vendors and enjoy the crisp fall air.
  More info: https://www.windsorevents.ca
• Erie Street Guided Walking Tour (Sept 6, 2025)
  Step back in time with Museum Windsor’s guided history tour of Erie Street. Tickets are just $6, making it a great budget-friendly outing for families and seniors.
  Register: https://bizxmagazine.com/fall-in-love-with-downtown-windsor-again-september-2025
• Beach Bash Volleyball Tournament (Sept 13, 2025)
  Cheer on local and visiting teams in downtown Windsor while supporting a community cause. It’s fun, energetic, and a chance to feel the sand without leaving the city.
  Details: https://bizxmagazine.com/fall-in-love-with-downtown-windsor-again-september-2025
• Windsor Half Marathon (Sept 14, 2025)
  Walk, jog, or cheer along the riverfront with incredible views of Detroit’s skyline. It’s open to all levels and makes a great memory for families and groups.
  Info: https://bizxmagazine.com/fall-in-love-with-downtown-windsor-again-september-2025
• Night Light Festival (Sept 18–20, 2025)
  Art Windsor–Essex lights up the city with digital art, projections, and interactive installations. There’s even a kids’ day and a DJ dance party. Many events are free.
  Schedule: https://artwindsoressex.ca/events-workshops/coming-soon-awe-night-light-festival-2025

Monarch Butterfly and Bird Migration

One of the most magical fall activities in Windsor Essex is watching the monarch butterflies and birds begin their long journey south. Migration usually starts in mid to late September, depending on the weather.

Head to Point Pelee National Park for the best viewing spots. The marsh boardwalk and the iconic tip of the park are prime areas to see butterflies and birds gathering before they cross Lake Erie. Seniors will find the boardwalk accessible and families will love the chance to teach kids about nature in action.

Plan ahead, as the timing of peak migration depends on temperature. Bring binoculars, a light jacket, and a camera—you’ll want to capture the moment.
More info: https://www.visitwindsoressex.com/event/fall-event-guide

Pick-Your-Own Orchards and Pumpkin Patches

If you love the idea of wandering through orchards with a basket in hand, Windsor Essex is perfect in autumn. Add apple picking, pumpkin patches, and sunflower fields to your fall activities list.

Family favourites include Wagner Orchards & Estate Winery, Meleg’s Lakeview Orchard, and Thiessen Orchards. Kids will love picking pumpkins, hayrides, and fresh donuts. Seniors can enjoy a stroll through the orchards and bring home local treats for Thanksgiving.

Tourism Windsor Essex has a handy Pick Your Own Guide to help you plan stops.
Guide: https://www.visitwindsoressex.com/event/fall-event-guide

Chrysler Canada Greenway

Looking for fun family fall activities that are active but still easy? Walk or cycle the Chrysler Canada Greenway, a 42 km trail that stretches from Windsor through small towns and farmland to Leamington.

In autumn, the trail is lined with fiery reds, golds, and oranges. Seniors will appreciate that it’s mostly flat and accessible, while families can ride bikes together at a comfortable pace. Pack a picnic, stop in a small town café, or just enjoy the scenery.

Trail info: https://en.wikipedia.org/wiki/Chrysler_Canada_Greenway

Windsor Sculpture Park and Tembo Day

Take a relaxing stroll along the Detroit River and you’ll find the Windsor Sculpture Park, home to more than 30 large outdoor art installations. It’s one of those autumn activities in Ontario that blends art and fresh air.

If you’re lucky enough to visit during Tembo Day, you can even help wash the beloved elephant sculpture—a quirky, fun activity for all ages. Bring your grandkids, snap a few pictures, and enjoy the crisp fall breeze.

Park info: https://en.wikipedia.org/wiki/Windsor_Sculpture_Park

Art Windsor–Essex (AWE)

Why You’ll Love These Autumn Activities

Why choose fall activities in Windsor Essex over anywhere else? It’s simple. The region combines affordability, accessibility, and authentic charm.

You can experience fall colours at Point Pelee, laugh at local festivals, enjoy fun family fall activities, and end the day with Caesars Windsor shows—all without draining your wallet. Seniors will love the walkable trails and gentle activities, while families will enjoy the interactive, kid-friendly events.

This is a chance to connect with loved ones, celebrate autumn, and create memories that you’ll be sharing over coffee for years to come.

Plan Your Trip to Windsor Essex This Fall

Here’s a simple way to plan a perfect day:

• Start your morning on a guided Erie Street history tour. check here: Erie Street Walking Tour – Tourism Windsor Essex Pelee Island
• Head to an orchard for apple or pumpkin picking.
• Stroll or bike part of the Chrysler Canada Greenway.
• Finish the evening with the Night Light Festival or a Caesars Windsor show. (use button earlier in post to book).

Don’t wait until the last minute. Hotels and events fill quickly in autumn. Book your stay, pack your cozy sweaters, and get ready to enjoy fall activities in Windsor Essex.

Conclusion

I truly can’t say this enough times that this is one of Canada’s truly best kept secrets.  In this post, I have only scratched the surface of things to do and see throughout the autumn in Windsor and surrounding communities. 

For nature walks to casino fun, outdoor barbeques to high end restaurants, there is an autumn activity in Windsor Essex for all.  If you need to get away but it needs to be a budget friendly holiday, I recommend you check out Windsor and Essex County.

Internal Links You Might Like:

• Things to Do in Windsor Essex: https://almurrayenterprises.net/southern-ontario-spots-windsor-essex-county-hamilton-niagara-falls/
• Fall in Toronto Guide: https://almurrayenterprises.net/fun-things-to-do-in-toronto-this-fall/
• Where to Go in Canada: https://almurrayenterprises.net/where-to-go-in-canada/

External References For You:

• Windsor Essex Fall Event Guide: https://www.visitwindsoressex.com/event/fall-event-guide
• Museum Windsor (Erie Street Tours): https://www.bac.lac-bac.gc.ca/eng/discover/mass-digitized-archives/Pages/museum-windsor.aspx
• Caesars Windsor Shows: https://www.caesars.com/caesars-windsor/shows
• Art Windsor–Essex: https://artwindsoressex.ca/events-workshops/coming-soon-awe-night-light-festival-2025

Please note: the opinions expressed in this post should never be construed as advice. The thoughts are based on my experiences and those of my friends and family. Whether traveling, exercising or other activity it is always a matter of personal preference.  Find what you like and enjoy and share if you want with us all!
Also: If considering a change in diet, exercise, nutrition and or supplements, you must consult your medical practitioner to make sure that what you are about to embark upon doesn’t interfere with your current treatments.