7 days in Windsor, Lakeshore & Essex Itinerary

7 days in Windsor, Lakeshore & Essex Itinerary

Created using Inspirock Ontario holiday planner

Make it your trip
Drive
1
Windsor
— 3 nights
Drive
2
Lakeshore
— 1 night
Drive
3
Essex
— 2 nights
Drive

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Windsor

— 3 nights
Canada's southernmost city, Windsor continues to play a key role in the country's automotive industry.
Windsor is known for casinos, breweries & distilleries, and parks. Your plan includes some of its best attractions: gain some tasty knowledge on a distillery tour, admire the natural beauty at Dieppe Gardens, examine the collection at Canadian Historical Aircraft Association, and get engrossed in the history at Mackenzie Hall.

For more things to do, where to stay, and more tourist information, you can read our Windsor travel itinerary planner.

Hamilton to Windsor is an approximately 3.5-hour car ride. You can also drive; or take a train; or fly. In November, daily temperatures in Windsor can reach 10°C, while at night they dip to 0°C. Finish up your sightseeing early on the 10th (Tue) so you can travel to Lakeshore.

Things to do in Windsor

Parks · Breweries & Distilleries · Tours · Museums
Find places to stay Nov 7 — 10:

Lakeshore

— 1 night
Lakeshore is a town on Lake St. On the 10th (Tue), see the interesting displays at John Freeman Walls Historic Site & Underground Railroad Museum, learn about winemaking at Wagner Orchards & Estate Winery, and then don't miss a visit to Belle River On the Lake.

To see other places to visit, reviews, where to stay, and other tourist information, use the Lakeshore trip itinerary planner.

Lakeshore is just a stone's throw from Windsor. Traveling from Windsor in November, expect Lakeshore to be a bit cooler, temps between -1°C and -10°C. On the 11th (Wed), you'll have the morning to explore before heading off to Essex.

Things to do in Lakeshore

Wineries · Museums
Find places to stay Nov 10 — 11:

Essex

— 2 nights
Essex is a town with a population of 20,427 in Essex County in southwestern Ontario, Canada, whose municipal borders extend to Lake Erie. Kick off your visit on the 11th (Wed): take an in-depth tour of Canadian Transportation Museum & Heritage Village, stroll around Lakeside Park, then learn about winemaking at Viewpointe Estate Winery, and finally learn about winemaking at Oxley Estate Winery. Keep things going the next day: stop by Cindy's Home & Garden, browse the fresh offerings at Lee and Maria's, learn about winemaking at Cooper's Hawk Vineyards and The Vines Restaurant, then learn about winemaking at Sprucewood Shores Estate Winery, and finally do a tasting at North 42 Degrees Estate Winery & Bistro 42.

To find other places to visit, photos, where to stay, and other tourist information, you can read our Essex trip itinerary planning tool.

Essex is just a stone's throw from Lakeshore. Expect a bit warmer temperatures when traveling from Lakeshore in November; daily highs in Essex reach 10°C and lows reach 0°C. Wrap up your sightseeing on the 13th (Fri) to allow time to drive back home.

Things to do in Essex

Wineries · Shopping · Museums · Parks

Side Trips

Find places to stay Nov 11 — 13: