The most dashing and fashionable cycling event to hit Windsor’s streets, the Windsor Tweed Ride, is back for the for 2023. Cyclists, dressed in their finest tweeds and old-time clothes, will leisurely take in some the city’s finest landmarks from Walkerville to Sandwich, and Erie to the waterfront.

So, what’s in store for the Tweed Ride? Here’s a look at our Ultimate Guide to Windsor’s most well dressed cycling event, the 2023 Windsor Tweed Ride!


When & where?

The ride starts and ends at WindsorEats, located at 400 Erie Street East. Registration starts at 12 noon on Saturday, May 13, 2023, with the ride departing at 1pm.


Is it a long route?

The route is about 15km long, but don’t let that intimidate you. It’s a slow, casual ride that’s broken up with several stops.


How much does it cost?

Tickets are $30 and are available here or from noon on at WindsorEats.


Will There Be Live Music?

Live classic early jazz including Django Reinhardt and vintage swing performed by The Superior Quartet, featuring local legends Phil Kane, Kevin Venney, Josh Zalev, and Andrew Lavasseur.


What Will There Be To Eat?

A selection of bites will be available along the ride including a special Tweed Ride menu in Sandwich Town.