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By Huuk Team

Road trip from Detroit to Milwaukee

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ITINERARY

7h 5m369 miles21 stops
1
Willistead Manor
1899 Niagara St, Windsor, Ontario N8Y 1K3 Canada
2
Amherstburg Navy Yard National Historic Site
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
3
Sprucewood Shores Estate Winery
7258 Cty Rd, 50 West, Harrow, Essex, Ontario N0R 1G0 Canada
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
4
The Ark
316 S Main St, Ann Arbor, MI 48104-2108
This music venue and nonprofit organization is dedicated to the presentation and encouragement of folk, roots and ethnic music through live performances by well-known and up-and-coming entertainers.
5
Corby's Irish Pub
441 E Lasalle Ave, South Bend, IN 46617-2723
6
Kelsey Museum of Archaeology
University of Michigan 434 South State Street, Ann Arbor, MI 48109
The Kelsey Museum houses a collection of nearly 100,000 objects from the civilizations of the Mediterranean.
7
Hudson Mills Metropark
8801 N Territorial Rd, Ann Arbor, MI 48130-9626
1,549-acre Park Has An 18-hole Golf Course.
8
Eastern Hills Golf Course
6075 E G Ave, Kalamazoo, MI 49004-9558
9
Kalamazoo Curling Club
3600 Vanrick Dr, Kalamazoo, MI 49001-0805
10
The Clover Room
1501 Fulford Street, Kalamazoo, MI 49001
11
New Vic Theatre
134 E Vine St, Kalamazoo, MI 49001-2602
Kalamazoo's New Vic Theatre was founded in 1966 by Kalamazoo residents Ted & Mary Jo Kistler. For over 45 years, The New Vic Theatre has entertained Southwest Michigan and Northern Indiana audiences carving a unique place for itself in the economy and theatrical tradition of the area.The New Vic's original production of "A Christmas Carol" (recipient of a "Special Tribute" from The State of Michigan in 1999) and the annual Christmas Concerts featuring The New Vic Theatre Chorus are among Kalamazoo's oldest on-going holiday presentations and have become an integral part of the holiday season for thousands of Southwest Michigan theatergoers.Located close to the heart of downtown Kalamazoo, the theatre's comfortable cabaret-style seating and intimate size, enhanced by a concession that serves a variety of hot & cold non-alcoholic beverages, lend to its unique atmosphere.The New Vic's flexible modular auditorium allows for innovative staging ranging from the complete round to conventional proscenium format. Efficient central heating and air conditioning allows for comfortable year-round operation.Of The New Vic's more than 325 productions to date, over 80% have been plays introduced to Kalamazoo audiences for the first time. Several plays ("Joseph and the Amazing Technicolor Dreamcoat", "Green Julia" by Paul Abelman, "Are You Now Or Have You Ever Been" and "The Memoirs Of Pontius Pilate" both by Eric Bentley) were presented to New Vic audiences prior to their Broadway premieres.The New Vic Theatre's season of productions begins in early February and runs through December 29 each year. January dates are normally reserved for the New Vic's popular January Concert Series, featuring a variety of musical groups or individual performers.Playing primarily weekends only -- except during the holidays when the performance schedule is greatly expanded -- and with only 100 available seats for each performance, The New Vic plays to over 10,000 theatre patrons annually bringing thousands of dollars to the downtown Kalamazoo area.The New Vic is a non-profit, tax-exempt corporation (New Vic Theatricals, Inc) and owns its own facility at 134 E. Vine St. in Kalamazoo.
12
Confections with Convictions
116 W Crosstown Pkwy, Kalamazoo, MI 49001-2732
Kalamazoo's only shop making hand crafted truffles and other confections exclusively from Fair Trade, organic certified chocolate. Chocolatier Dale Anderson's original recipes contain fresh local fruits, honey, and maple syrup. Vegan and gluten free options are always available. Closed Sunday and Monday. Open Tuesday thru Saturday 10 a.m. until 6:00 p.m.
13
O'Duffy's Pub
804 W Vine St, Kalamazoo, MI 49008-1157
14
O'Rourke's Public House
1044 E Angela Blvd, South Bend, IN 46617-1374
15
Basilica of the Sacred Heart
114 Coleman Morse Ctr University of Notre Dame, South Bend, IN 46556-4617
16
The 900 Shops Mall
900 N Michigan Ave, Chicago, IL 60611-1542
17
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
18
Museum Of Illusions Chicago
25 E Washington St, Chicago, IL 60602-1708
19
Boystown
Chicago, IL
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
20
Wrigley Field
1060 W. Addison St., Chicago, IL 60613-4566
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
21
The Riverside Theater
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
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OVERVIEW

Get ready for an exciting adventure as we travel from the vibrant city of Detroit to the charming city of Milwaukee! Our journey will take us through picturesque landscapes, bustling towns, and along the sparkling waters of Lake Michigan. Along the way, we'll discover hidden gems, learn about the region's rich history, and create memories that will last a lifetime.

Our adventure begins in the heart of Detroit, where towering skyscrapers and bustling streets tell the story of a city on the rise. From here, we'll set out on our journey, winding our way through the rolling hills and lush forests of Michigan. As we cross the state line into Wisconsin, the scenery transforms into a tapestry of dairy farms and charming small towns. The vibrant colors of autumn leaves will paint the landscape in hues of gold, orange, and crimson, creating a breathtaking backdrop for our travels.

As we approach Milwaukee, the sparkling waters of Lake Michigan will come into view. The city's skyline, dotted with historic buildings and modern skyscrapers, will welcome us to our final destination. Milwaukee's rich German heritage is evident in its architecture, cuisine, and lively festivals, making it a perfect place to end our adventure and celebrate the journey we've shared.

1
Start:Willistead Manor
Windsor, Ontario·
4.5
(98) review
1899 Niagara St, Windsor, Ontario N8Y 1K3 Canada
2
Amherstburg Navy Yard National Historic Site
Amherstburg, Ontario·
5.0
(94) review
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
3
Sprucewood Shores Estate Winery
Harrow, Essex, Ontario·
4.5
(97) review
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
7258 Cty Rd, 50 West, Harrow, Essex, Ontario N0R 1G0 Canada
4
The Ark
Ann Arbor, Michigan·
4.5
(93) review
This music venue and nonprofit organization is dedicated to the presentation and encouragement of folk, roots and ethnic music through live performances by well-known and up-and-coming entertainers.
316 S Main St, Ann Arbor, MI 48104-2108
5
Corby's Irish Pub
South Bend, Indiana·
3.5
(9) review
441 E Lasalle Ave, South Bend, IN 46617-2723
6
Kelsey Museum of Archaeology
Ann Arbor, Michigan·
4.5
(99) review
The Kelsey Museum houses a collection of nearly 100,000 objects from the civilizations of the Mediterranean.
University of Michigan 434 South State Street, Ann Arbor, MI 48109
7
Hudson Mills Metropark
Ann Arbor, Michigan·
4.5
(95) review
1,549-acre Park Has An 18-hole Golf Course.
8801 N Territorial Rd, Ann Arbor, MI 48130-9626
8
Eastern Hills Golf Course
Kalamazoo, Kalamazoo County, Michigan·
3.5
(4) review
6075 E G Ave, Kalamazoo, MI 49004-9558
9
Kalamazoo Curling Club
Kalamazoo, Kalamazoo County, Michigan·
5.0
(3) review
3600 Vanrick Dr, Kalamazoo, MI 49001-0805
10
The Clover Room
Kalamazoo, Kalamazoo County, Michigan·
5.0
(3) review
1501 Fulford Street, Kalamazoo, MI 49001
11
New Vic Theatre
Kalamazoo, Kalamazoo County, Michigan·
4.5
(9) review
Kalamazoo's New Vic Theatre was founded in 1966 by Kalamazoo residents Ted & Mary Jo Kistler. For over 45 years, The New Vic Theatre has entertained Southwest Michigan and Northern Indiana audiences carving a unique place for itself in the economy and theatrical tradition of the area.The New Vic's original production of "A Christmas Carol" (recipient of a "Special Tribute" from The State of Michigan in 1999) and the annual Christmas Concerts featuring The New Vic Theatre Chorus are among Kalamazoo's oldest on-going holiday presentations and have become an integral part of the holiday season for thousands of Southwest Michigan theatergoers.Located close to the heart of downtown Kalamazoo, the theatre's comfortable cabaret-style seating and intimate size, enhanced by a concession that serves a variety of hot & cold non-alcoholic beverages, lend to its unique atmosphere.The New Vic's flexible modular auditorium allows for innovative staging ranging from the complete round to conventional proscenium format. Efficient central heating and air conditioning allows for comfortable year-round operation.Of The New Vic's more than 325 productions to date, over 80% have been plays introduced to Kalamazoo audiences for the first time. Several plays ("Joseph and the Amazing Technicolor Dreamcoat", "Green Julia" by Paul Abelman, "Are You Now Or Have You Ever Been" and "The Memoirs Of Pontius Pilate" both by Eric Bentley) were presented to New Vic audiences prior to their Broadway premieres.The New Vic Theatre's season of productions begins in early February and runs through December 29 each year. January dates are normally reserved for the New Vic's popular January Concert Series, featuring a variety of musical groups or individual performers.Playing primarily weekends only -- except during the holidays when the performance schedule is greatly expanded -- and with only 100 available seats for each performance, The New Vic plays to over 10,000 theatre patrons annually bringing thousands of dollars to the downtown Kalamazoo area.The New Vic is a non-profit, tax-exempt corporation (New Vic Theatricals, Inc) and owns its own facility at 134 E. Vine St. in Kalamazoo.
134 E Vine St, Kalamazoo, MI 49001-2602
12
Confections with Convictions
Kalamazoo, Kalamazoo County, Michigan·
5.0
(92) review
Kalamazoo's only shop making hand crafted truffles and other confections exclusively from Fair Trade, organic certified chocolate. Chocolatier Dale Anderson's original recipes contain fresh local fruits, honey, and maple syrup. Vegan and gluten free options are always available. Closed Sunday and Monday. Open Tuesday thru Saturday 10 a.m. until 6:00 p.m.
116 W Crosstown Pkwy, Kalamazoo, MI 49001-2732
13
O'Duffy's Pub
Kalamazoo, Kalamazoo County, Michigan·
4.5
(9) review
804 W Vine St, Kalamazoo, MI 49008-1157
14
O'Rourke's Public House
South Bend, Indiana·
4.5
(9) review
1044 E Angela Blvd, South Bend, IN 46617-1374
15
Basilica of the Sacred Heart
South Bend, Indiana·
5.0
(700) review
114 Coleman Morse Ctr University of Notre Dame, South Bend, IN 46556-4617
16
The 900 Shops Mall
Chicago, Illinois·
4.0
(96) review
900 N Michigan Ave, Chicago, IL 60611-1542
17
Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
333 Michigan Ave, Chicago, IL 60601-3901
18
Museum Of Illusions Chicago
Chicago, Illinois·
4.5
(97) review
25 E Washington St, Chicago, IL 60602-1708
19
Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
Chicago, IL
20
Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
1060 W. Addison St., Chicago, IL 60613-4566
21
The Riverside Theater
Milwaukee, Wisconsin·
4.0
(95) review
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
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FAQ
Frequently Asked Questions
What's the driving distance between Detroit and Milwaukee?
The distance is 369 miles
What's the travel time between Detroit and Milwaukee?
The driving time can vary depending on traffic conditions, but it is typically 7h 5m mins in normal traffic
What are some of the best cities to visit between Detroit and Milwaukee?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Milwaukee?
There are plenty! Here are some stops you shouldn’t miss on your way to Milwaukee
What’s the weather like in Milwaukee?
The weather in Milwaukee is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Milwaukee in January
Weather in Milwaukee in February
Weather in Milwaukee in March
Weather in Milwaukee in April
Weather in Milwaukee in May
Weather in Milwaukee in June
Weather in Milwaukee in July
Weather in Milwaukee in August
Weather in Milwaukee in September
Weather in Milwaukee in October
Weather in Milwaukee in November
Weather in Milwaukee in December
Interested in a detailed plan for your time in Milwaukee?
Plan your dream Milwaukee trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Milwaukee
A 2-day itinerary in Milwaukee
A 3-day itinerary in Milwaukee
A 4-day itinerary in Milwaukee
A 5-day itinerary in Milwaukee
A 6-day itinerary in Milwaukee
Where else can I travel to if I'm starting my trip in Detroit?
We have a lot of great trip options for Detroit! See the links below for all the itineraries we created for you