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Windsor (Ontario) to Milwaukee drive

(tap on any row to expand for more details)

  Windsor (Ontario)
 Ann Arbor
 Saint Joseph (Michigan)
 Museum of Science and Industry
 Mars Cheese Castle
driving   /   2 days   /   no pets   /   no RV

Rooms:     Travelers:

Windsor (Ontario) to Milwaukee road trip planner

Here's a sample itinerary for a drive from Windsor (Ontario) to Milwaukee. If you're planning a road trip to Milwaukee, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Windsor (Ontario) and Milwaukee. Camping along the way? View RV campgrounds between Windsor (Ontario) and Milwaukee. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

customize this trip
 Day 1

11:00 am  start in Windsor (Ontario)
drive for about 51 minutes

11:51 am  Ann Arbor
stay for about 1 hour
and leave at 12:51 pm
drive for about 1.5 hours

2:34 pm  Kalamazoo
stay for about 1 hour
and leave at 3:34 pm
drive for about 57 minutes

4:31 pm  Saint Joseph (Michigan)
stay overnight and leave the next day around 11:00 am

day 1 driving ≈ 3.5 hours

 Day 2

11:00 am  leave from Saint Joseph (Michigan)
drive for about 1.5 hours

12:20 pm  Museum of Science and Industry
stay for about 1 hour
and leave at 1:20 pm
drive for about 1.5 hours

2:40 pm  eat at Mars Cheese Castle
stay for about 1 hour
and leave at 3:40 pm
drive for about 44 minutes

4:25 pm  arrive in Milwaukee

day 2 driving ≈ 3.5 hours

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Enter a city to drive through, or find all trips from Windsor (Ontario) to Milwaukee.

Where should I stop along the way?

Ann Arbor  (11 answers)
    Zingerman's Delicatessen  (3 mentions)
    questions about Ann Arbor:
        What's the best neighborhood in Ann Arbor for a first time visitor?
        Ann Arbor: reccomended activities

Kalamazoo  (11 answers)
    Air Zoo  (2 mentions)
    restaurants around Kalamazoo:
        Bell's Brewery, Inc: Brewery
        Arcadia Brewing Company Kalamazoo
        The Union Cabaret & Grille
        Old Dog Tavern
    questions about Kalamazoo:
        What's the best neighborhood in Kalamazoo for a first time visitor?
        Best free things to do in Kalamazoo?
        What is your favorite restaurant in Kalamazoo?

Saint Joseph (Michigan)  (2 answers)

Museum of Science and Industry  (33 mentions)

Mars Cheese Castle  (2 mentions)

Where's the best place to eat in Milwaukee?

Need some recommendations on somewhere to get food?

Trippy members suggest Milwaukee Brat House, which was mentioned 3 times.

Here are some more restaurants people talk about:

Cafe Centraal  (2 mentions)
Lulu Cafe  (2 mentions)
Cafe Benelux & Market  (2 mentions)

Want to research more popular restaurants in Milwaukee? Click the blue button below.

What are some things to do in Milwaukee?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Milwaukee Art Museum  (8 mentions)
Lakefront Brewery  (3 mentions)
Usinger's  (3 mentions)
Discovery World  (3 mentions)

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

For example, here are some questions people have asked about Milwaukee. Click on any question to see answers from the community!

profile  Katie from Los Angeles asked:
What's the best neighborhood in Milwaukee for a first time visitor?  (6 answers)

profile  Bonnie from United States asked:
What's not to miss in Milwaukee?  (5 answers)

profile  Keith from Denver asked:
Family-friendly restaurants to experience Midwest foods  (3 answers)

profile  Travis from Des Moines asked:
Milwaukee Food and Bars?  (2 answers)

profile  Casey from Cambridge (Massachusetts) asked:
Need a beer guide in Milwaukee  (2 answers)

Click the button below to explore more questions and answers related to Milwaukee.

Do I really have to go back home?

Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Milwaukee to Windsor (Ontario) drive, or go to the main page to plan a new road trip.

You can also compare the travel time if you're flying or driving by calculating the distance from Windsor (Ontario) to Milwaukee. Or get a full Windsor (Ontario) to Milwaukee flight plan.

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend.

And if you know Windsor (Ontario) well, please help your fellow travelers and answer their questions about Windsor (Ontario)!

At a Glance
without making any stops
total driving distance is 388 miles
driving time of 5 hours, 54 minutes
Milwaukee is 1 hour behind Windsor (Ontario)
10 Windsor (Ontario) travel answers
11 Ann Arbor travel answers
11 Kalamazoo travel answers
2 Saint Joseph (Michigan) travel answers
33 Milwaukee travel answers


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