Field Guides/Wine Trail Ride
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CategoryFood Drink · Cycling
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Wine Trail Ride.

Guided weekend cycling tours visiting Windsor-Essex wineries with tastings and a progressive meal

Wine Trail Ride
01 — About

The brief.

Run by WindsorEats, Wine Trail Ride leads guided bicycle tours through the Windsor-Essex farmlands along the Lake Erie coastline, riding quiet country roads and the Chrysler Greenway Trail. Each roughly five-hour ride covers about 30km with four stops, pouring at least 12 wines paired with a progressive meal across the day. Bicycles, helmets and a guide are provided; tours run for groups of up to 20 riders. The program earned the Ontario Culinary Tourism Alliance's Best Culinary Tourism Experience (2009) and TIAC's Innovator of the Year (2010). WindsorEats partners with the Essex Region Conservation Authority on tree-planting and pays guides a living wage.

02 — Programs

2. ways in.

  1. 01

    Wine Trail Ride

    For: Adults 19+When: May–October (weekends)

    An approximately five-hour guided bicycle tour covering about 30km with four stops, pouring at least 12 wines paired with a progressive feast. Includes a bicycle, helmet, tastings, food and a guide. Maximum 20 riders.

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  2. 02

    Private & Corporate Rides

    For: Adults 19+ / private groupsWhen: Year-round, any day by arrangement

    Privately scheduled versions of the Wine Trail Ride for corporate and private groups, bookable any day of the week on a chosen date rather than the regular weekend schedule.

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03 — Notable

Worth knowing.

  1. 01Rides run every weekend from May through October; private/corporate rides are available year-round.Source ↗
  2. 02Tours are approximately five hours long with a maximum of 20 riders, for guests 19 years of age and older.Source ↗
  3. 03The route covers a 30km journey with four stops and at least 12 different wines plus a progressive feast.Source ↗
  4. 04Won the Ontario Culinary Tourism Alliance's Best Culinary Tourism Experience (2009) and TIAC's Innovator of the Year (2010).Source ↗
  5. 05WindsorEats partners with the Essex Region Conservation Authority on tree-planting, contributing from every ticket sold.Source ↗
04 — Visit

Get in
touch.

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AER’s guide to Wine Trail Ride · Compiled from winetrailride.caLast verified 2026-06-02