Labor Day Weekend Road Trip: Four days, five states, 2,500 miles

Well, Silly Americans it is Labor Day weekend here in the United States of America and I have been blessed with four days off from work in a row. And that can only mean one thing: a LABOR DAY WEEKEND ROAD TRIP!

I’m packing up my car for the long holiday weekend and driving to Mount Rushmore and back! Can you believe I have never before seen those four giant presidents carved into the side of a rock live and in person ever before? It’s my dream come true and a dream road trip for any Silly American adventurer!

Don’t worry — Mount Rushmore isn’t the only site I plan to see on this adventure! I have a fully packed road trip itinerary including monuments, tourist traps, and roadside attractions (including Crazy Horse, Carhenge, Wall Drug, and Flintstone Bedrock City just to name a few) and have mapped out everywhere on the route that I hope to go to.

We’re taking I-90 the whole way there (through Wisconsin and Minnesota) and I-80 the whole way back (through Nebraska and Iowa). There will surely be plenty of roadside attractions and other silly sites to check out on our four-day road trip to Mount Rushmore from Chicago (and back! Check out the map below to see what those stops will hopefully include.

Labor Day Weekend Road Trip Map

OK, so maybe that Labor Day Weekend road trip itinerary is a bit ambitious. But I always find it better to over plan than to under plan! I know I won’t be able to see EVERYTHING I want, so let’s see how many midwestern roadside attractions I can see in four days, five states, and 2,500 miles…

Catch you on the flip side of my South Dakota vacation with plenty of photos from Wisconsin, Minnesota, South Dakota, Nebraska, and Iowa!

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Valerie Bromann

Founder & ROad Trip Expert

Valerie Bromann is a a website manager, content creator, and writer from Chicago, Illinois (currently living in Dallas, Texas). As an avid road tripper who has visited hundreds of roadside attractions, Val always pull over for a world’s largest thing. Founder of Silly America and author of The Road Trip Journal & Activity Book, she visits, photographs, and writes about all the weird tourist destinations she visits and offers road trip planning advice and inspiration based on her own travels so you can hit the road for yourself.

World's Largest Mailbox in Casey, Illinois roadside attraction

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Last modified: November 16, 2023

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The Road Trip Journal & Activity Book - Everything You Need to Have and Record an Epic Road Trip! By Valerie Bromann

The Road Trip Journal & Activity Book

Everything You Need to Have and Record an Epic Road Trip!

BY Valerie Bromann

Enjoy fun games and challenges to pass the time on your next road trip and have a keepsake to look back on for years to come with this entertaining must-have for your next vacation.

The road trip you’ve been dreaming of starts here! Journal about your stops and get to know your fellow passengers with activities and exercises designed to pass the time and bring you closer together. Instead of “Are we there yet?” you’ll find yourself asking, “We’re there already?”. Complete with prompts you can turn to while driving between locations, this journal will one day be a memento of your life-changing trip.