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By Huuk Team

Road trip from Toledo to Anchorage

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ITINERARY

76h 14m3,821 miles10 stops
1
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.
2
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
3
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.
4
Alliant Energy Center
1919 Alliant Energy Center Way, Madison, WI 53713-1400
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
5
First Unitarian Meeting House of Madison
900 University Bay Dr, Madison, WI 53705-2298
6
Norseman Distillery
451 Taft St NE Suite 19, South Loading Dock, Minneapolis, MN 55413-2831
Norseman Distillery, the first micro-distillery in Minneapolis, was founded with principles of using the very best local ingredients to produce small batches of exceptionally fine spirits. From our micro-distillery in northeast Minneapolis, we hand craft each batch with the hopes of inspiring legendary cheer in those who drink it.
7
Girdwood Brewing Company
2700 Alyeska Highway, Girdwood, Anchorage, AK 99587
Enjoy local brews and epic views of the Chugach mountains at Girdwood Brewing Company. We have a beautiful timber framed taproom adorned with local art and ski relics. For those who prefer the outdoors, there’s an awesome beer garden with fire pits and plenty of seating. We offer up four core beers and a series of rotating taps. Root beer, cold brew coffee, and kombucha are available for those looking for an alcohol free beverage. Tasters and 12 ounce pours are available to drink in the taproom. If you are looking for beer to go, we fill growlers, sell 5 gallon kegs, and have 4-packs of 16 ounce cans with labels designed by Alaskan artists (for sale in the taproom only). Food trucks are on-site every day, and we have cool merchandise for you to take home. Girdwood Brewing Company is truly rooted in our community. We donate to a number of nonprofits and outdoor adventure organizations. Our brewery also provides year round employment to over a dozen locals.
8
Jazzy Gourmet Popcorn
11823 Old Glenn Hwy Next to Jalapeños, Anchorage, AK 99577-7751
Jazzy Gourmet Popcorn’s owner, Mr. Roland’s inspiration for starting this business was his brother, an owner of one of Houston’s most popular popcorn establishments. JGP offers free samples of over 50 flavors of gourmet popcorn. We have gourmet flavors to please every palate including sweet, savory or spicy. If you’re feeling a little nutty, we offer flavors with cashews, pecans, walnuts & more.
9
Planet Walk
5th & G Street Kincaid Park, Anchorage, AK
10
Four Seasons Trans Group
1020 W 12th Ave, Anchorage, AK 99501-4577
We provide shuttle services within Anchorage, Seward, Talkeetna, Whittier, Palmer, Wasilla, and Girdwood.
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OVERVIEW

1
Start: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
2
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
3
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
4
Alliant Energy Center
Madison, Wisconsin·
4.0
(99) review
Our premier downtown multi-venue complex features four unique and versatile venues: Veterans Memorial Coliseum, Exhibition Hall, the New Holland Pavilions, and Willow Island. A top choice for expositions, conventions, meetings, concerts, sporting events, ag events, and much more, the Alliant Energy Center complex is a one-stop-shop for all your events. Ample parking, mouthwatering catering, dedicated staff, and a full range of rental equipment & high speed internet make AEC an event planners delight!
1919 Alliant Energy Center Way, Madison, WI 53713-1400
5
First Unitarian Meeting House of Madison
Madison, Wisconsin·
4.5
(96) review
900 University Bay Dr, Madison, WI 53705-2298
6
Norseman Distillery
Minneapolis, Minnesota·
5.0
(98) review
Norseman Distillery, the first micro-distillery in Minneapolis, was founded with principles of using the very best local ingredients to produce small batches of exceptionally fine spirits. From our micro-distillery in northeast Minneapolis, we hand craft each batch with the hopes of inspiring legendary cheer in those who drink it.
451 Taft St NE Suite 19, South Loading Dock, Minneapolis, MN 55413-2831
7
Girdwood Brewing Company
Girdwood, Anchorage, Alaska·
4.5
(97) review
Enjoy local brews and epic views of the Chugach mountains at Girdwood Brewing Company. We have a beautiful timber framed taproom adorned with local art and ski relics. For those who prefer the outdoors, there’s an awesome beer garden with fire pits and plenty of seating. We offer up four core beers and a series of rotating taps. Root beer, cold brew coffee, and kombucha are available for those looking for an alcohol free beverage. Tasters and 12 ounce pours are available to drink in the taproom. If you are looking for beer to go, we fill growlers, sell 5 gallon kegs, and have 4-packs of 16 ounce cans with labels designed by Alaskan artists (for sale in the taproom only). Food trucks are on-site every day, and we have cool merchandise for you to take home. Girdwood Brewing Company is truly rooted in our community. We donate to a number of nonprofits and outdoor adventure organizations. Our brewery also provides year round employment to over a dozen locals.
2700 Alyeska Highway, Girdwood, Anchorage, AK 99587
8
Jazzy Gourmet Popcorn
Anchorage, Alaska·
4.0
(7) review
Jazzy Gourmet Popcorn’s owner, Mr. Roland’s inspiration for starting this business was his brother, an owner of one of Houston’s most popular popcorn establishments. JGP offers free samples of over 50 flavors of gourmet popcorn. We have gourmet flavors to please every palate including sweet, savory or spicy. If you’re feeling a little nutty, we offer flavors with cashews, pecans, walnuts & more.
11823 Old Glenn Hwy Next to Jalapeños, Anchorage, AK 99577-7751
9
Planet Walk
Anchorage, Alaska·
3.5
(8) review
5th & G Street Kincaid Park, Anchorage, AK
10
Four Seasons Trans Group
Anchorage, Alaska·
5.0
(98) review
We provide shuttle services within Anchorage, Seward, Talkeetna, Whittier, Palmer, Wasilla, and Girdwood.
1020 W 12th Ave, Anchorage, AK 99501-4577

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Toledo and Anchorage?
The distance is 3,821 miles
What's the travel time between Toledo and Anchorage?
The driving time can vary depending on traffic conditions, but it is typically 76h 14m mins in normal traffic
What are some of the best cities to visit between Toledo and Anchorage?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Anchorage?
There are plenty! Here are some stops you shouldn’t miss on your way to Anchorage
What’s the weather like in Anchorage?
The weather in Anchorage is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Anchorage in January
Weather in Anchorage in February
Weather in Anchorage in March
Weather in Anchorage in April
Weather in Anchorage in May
Weather in Anchorage in June
Weather in Anchorage in July
Weather in Anchorage in August
Weather in Anchorage in September
Weather in Anchorage in October
Weather in Anchorage in November
Weather in Anchorage in December
Interested in a detailed plan for your time in Anchorage?
Plan your dream Anchorage trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Anchorage
A 2-day itinerary in Anchorage
A 3-day itinerary in Anchorage
A 4-day itinerary in Anchorage
A 5-day itinerary in Anchorage
A 6-day itinerary in Anchorage
Where else can I travel to if I'm starting my trip in Toledo?
We have a lot of great trip options for Toledo! See the links below for all the itineraries we created for you