Fall 2020 Bucketlist: Social Distant Edition

September 22, 2020

Every year for the past 3 or 4 years, I do a Chicago bucketlist. But with Covid this year, 2020 has been a year like no other. This fall, we are limited with certain things to do, so I put together a fall bucketlist of socially distant things to do around Chicago that are still safe (and with wearing a mask of course). So here are a few things we have already done or planning on to do this fall (obviously a lot depends on our city’s data. Check with places before booking for all restrictions and please alway wear a mask).


I just did this a week ago for the first time and it was so much fun! We did the nighttime tour from the Riverwalk location, which is only an hour. Perfect beginner kayakers and the views are beautiful. We rented them through Urban Kayaks. You can book a reservation with them online. It’s a good social distant activity because everyone has their own kayak and masks/distance are required while on the Riverwalk.

Kayaking on the Chicago River is a great thing to do this fall that is socially distant and lots of fun.
Night tour with Urban Kayaks

Segway Tour

This has been on my bucketlist for awhile now! There are a few different companies that do it, but the Absolutely Chicago Segway Tours have been around for some time now. It looks like such a fun social distant activity and a cool way to see the city. They will run into late October.

Jack’s Pumpkin Pop Up

This is returning this year, but looks a little different. There are still lots of opportunities to take photos, do the corn maze and you can actually now purchase pumpkins. No alcohol or food to purchase, so plan accordinly, especially if you are bringing the little ones. Kids under 4 are free and I thought Noah was a great age. Mila (2 years old) didn’t enjoy it as much.

Masks are required (and they were enforcing it to those not wearing them), take your quick photos and put your mask back on 🙂

leggings // shoes // scarf // sweater is from one of my favorite boutiques Vintage Charm

Visit a park

We’ve been doing a lot of park and forest preserve visits lately and have a few favorites. Henry Palmisano Park in Bridgeport is a huge park with lots of room to social distance. Another city park is Osaka Gardens in Jackson Park. It’s beautiful & good for picnics.

Osaka Gardens

Skokie Lagoons, Harms Wood in Glenview or The Sculpture Park in Schaumburg has been on our list too!

If you use the #CGLMidwestTravel on Instagram, you can see all the parks and forest preserves we’ve been to recently.

Henry Palmisano Park

Take the Metra

My dad is the one that actually mentioned we bring the kids on the Metra. He takes it to work everyday and said ridership is down over 90% and it would be fun for the kids. So we all went down to Union Station and took the train to the suburbs. We were the only ones of our car the way there and maybe had 8 people on the way back to the city. Masks are required (we didn’t see anyone without them actually) and seating is every other row. The kids loved it and we felt like it was the closest thing to travel we’ve done in a while.

We took the Metra Train to the suburbs and had the entire car to ourselves since ridership is down right now. Masks are required and seating is every other row.
We took the Metra Train to the suburbs and had the entire car to ourselves since ridership is down right now. Masks are required and seating is every other row.
The Single Baby Jogger is one of best strollers we have. It’s lightweight and the bottom has a large storage area.

Travel the Midwest

Some of our favorite locations are Galena, IL, Saugatuck, MI, Pine Creek, IL, Milwaukee, WI, and New Buffalo, MI area. I have a few blog post on these areas you can click on them below. We have not been back since Covid, so please check before booking.

Since airplane travel is not very popular right now, taking road trips around the Midwest is a fun activity. Saugatuck, MI is a cute town in Michigan with lots to do on the water, at an apple orchard
Downtown Saugatuck

Rent an eletronic boat

This was one of the most fun activities I have done with my friends in awhile! We rented an electronic boat (4 people plus two minors allowed right now) and we went up and down the Chicago River. You can bring your own food and drinks too. We drove the boat, but hiring a driver is also an option. You can use code Christine50 for $20 dollars off your rental! We rented them from the Rockwell location, which is so nice. It’s not crowded and Metropolitan Brewery is located there too. Masks are required on the dock.

I have a highlight on my Instagram page right now for more details!

Rockwell on the River is a hidden dock and brewery on the north brand of the Chicago River. Definitely add it your fall bucketlist!
Rockwell on the River and Metropolitan Brewery

Visit an apple orchard or pumpkin patch

There are many around the Chicagoland area. We plan on visiting one soon, but here are a few we’ve been to that are rather large and could be distant!

  • Appler Holler
  • Goebert’s Farm
  • Cranes Apple Orchard
  • Johnson’s Farm

Dine on a Patio

Since al fresco dining is probably going to be extended well into the winter this year, I put together a list of patios and rooftops in the city. Whether you are comfortable dining out now or for later, there are a variety of options from casual, family to fine dining.

Patio dining will be extended into the late fall this year so there are plenty of options to add to your fall bucketlist this year.
Island Party Hut

I hope some of these are things you might do this fall. Whether it is for now or your next fall bucketlist, save them! And if you do any of them, let me know!

Until next time,


  1. […] There is also pan de muerto that you can also look up how to make as well. This goes directly onto the altar too! We hope these recipes and ideas inspire you to make your own Day of the Dead altar this weekend. If you make anything, tag me @thechicagogoodlife or if you want a Chicago Bucketlist this fall, read more here. […]

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