5 Things to Do on Your Perfect Fall Weekend in the Midwest

Marissa Rivera

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5 Things to Do on Your Perfect Fall Weekend in the Midwest

Thinking of a weekend escape this fall? Pack your How-to-Be Nice for Dummies book and pay a visit to the Midwest. 

Even though that’s not a real book, what’s real is the spoon-full of niceness Midwesterners will serve alongside their great hospitality. Ask anyone who has visited any of the 12 states that make up the region: North Dakota, South Dakota, Nebraska, Minnesota, Iowa, Missouri, Wisconsin, Illinois, Kansas, Michigan, Indiana, and Ohio. 

Once known as a stopover for airlines in the 1950s and 1960s, the Midwest is centrally located between both coasts making it a conveniently located destination for a long weekend escape with friends and family or a romantic weekend with your SO. The region offers a variety of experiences and accommodations to plan a balanced getaway. From quintessential small towns to comfort foods and spirits, to outdoor activities and professional sporting events. Don’t know where to go or what to do for your Midwestern weekend escape this fall? Here are my suggestions:

1. Watch your favorite team play 

Plan your visit around an away game for your favorite professional football team. With eight teams in the region, you are sure to catch a game this season.

Three years ago we planned a trip to the Midwest to see my favorite team play and it’s one of my best trips by far. The trip was planned around seeing my team play at their home stadium so that’s all we really planned for. We didn’t expect anything more than watching football with over 80,000 people but along the way, we discovered there’s more than farmland in the Midwest. Every time someone asks me what’s one of the most memorable trips I’ve been on they are pleasantly surprised to learn that this trip makes the top of my list.

Football Game in Lambeau Field

Green Bay, Wisconsin Photo by @connornystrom

2. Stay in a small town 

Instead of staying close to the sporting event, look for a hotel in a quintessential town outside of the city. This might open more hotel options while escaping the hustle and bustle of a large city for a tranquil, relaxing experience. After all, you have to save your energy to cheer on your team.

Instead of staying in Green Bay where the game was taking place, we stayed in Delafield, Wisconsin at a boutique hotel that was priced comparable to the hotel chains near the stadium.

3. Make stops along the waya

Chances are you will put a lot of miles onto your car rental in the Midwest, so break up the ride by making stops along the way. You might find numerous fall activities along the way to make your IG feed look like a PSL ad.  

On the drive to Green Bay, we stumbled upon a family farm with a pumpkin patch, a petting zoo, and a corn maze – which we were determined to complete even though we were cutting it close to game start time.

4. Celebrate all things fall

If you live in a city as I do, you might notice its fall time by the highly anticipated return of pumpkin-spiced lattes or the additional hard cider options on draft at your favorite bar. Take those PSL orders to-go and celebrate fall harvest at one of the many fall festivals the Midwest puts on throughout the season. From Applefest to Oktoberfest or even  Sputnickfest – celebrating the 1962 crash landing of a 20-pound piece of Russia's Sputnik on a street in Wisconsin – the Midwest offers hundreds of festivals.

 Pro tip:  Luckily for you, this website has a full list organized by weekends. You’re welcome. 

We wish someone would have given us a heads up about this pro tip as we didn’t get a chance to check out local festivals during our visit. At least we were fortunate enough to sample fall flavors at restaurants. Many offered fall-inspired daily specials and outstanding seasonal spirits and brews. 

View at Apple Holler

Photo by @outdoorracine

5. Arrive and depart from a different airport

Depending on which area of the Midwest you choose, you might only be within a 2-hour radius from a different airport than the one you flew to. This is more common with the states bordering the Great Lakes so do your homework in advance – you just might be able to take a later flight home and explore more of the region while crossing off another state from your bucket-list. 

We spent most of our 72-hours in Wisconsin consuming cheese for every meal of the day and ended the trip in Illinois. Leaving from Chicago allowed us to sleep in after the big game by catching a later flight. Our trip happened to coincide with the Chicago Marathon so we got to fly home with runners sporting their new medals – it was pretty cool!

Pro Tip

Check airports at neighboring states.

Whether you are on a business trip that takes you to the region or looking for a trip to use those two days of vacation you have left for the year, the Midwest should be on the top of your list. With moderate temperatures, the fall season is the ideal time of the year to visit and attend a football game, go on a road trip or enjoy a fall festival. 

If you only have 48-hours in the region, stay in a small town and attend a football game for the perfect balance between Sunday fun day and a relaxing weekend. Dine out at a local restaurant and make new friends –– Midwesterners are some of the nicest people I’ve met during my travels. One day we ate lunch at a local tavern where the waiters welcomed us like locals. By the end of the meal, it was like parting with a friend we hadn’t seen in years, telling us what was new in town and what we must see before we went back home.  Kick start your last day by eating breakfast where the locals recommend. (That’s where your new friends come in 😌 )

Marissa Rivera
New York City, United States
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