5 Things to Do Oct. 8-10 — Highwood Pumpkin Fest, Lincoln Park Wine Fest, Cheer on Chicago Marathon Runners, and More

It’s going to be a busy fall weekend around Chicago and the North Shore! From the Great Highwood Pumpkin Festival and Skeleton Invasion, to the Bank of America Chicago Marathon, here are five of the best events to check out.

Check out each event’s website for current Covid-19 safety measures and possible cancelations.

All Weekend: Virtual Open House Chicago

A popular highlight of the season, Open House Chicago is a celebration of architecturally, culturally, and historically significant sites across Chicago’s many neighborhoods. This fall, the festival will feature its new and improved Open House Chicago App, the return of in-person site visits from Oct. 16-17, and a series of virtual programs.

Oct. 8-10: The Great Highwood Pumpkin Festival & Skeleton Invasion

17 Highwood Ave., Highwood

31 of the Best Things to Do in Chicago This October

Pumpkins and skeletons will descent upon Highwood for a spooky family-friendly weekend! With multiple photo opportunities, including a great pumpkin wall and themed skeletons, Highwood is the place to be Oct. 8-10. There is no entry fee, and attendees are encouraged to “BYOP” (place their own personal pumpkins) on walls if they wish, or they can carve one at the festival. Proceeds from the festival will benefit Highland Park High School Charity Drive.

Oct. 8-9: Lincoln Park Wine Fest

Jonquil Park, 1001 W. Wrightwood Ave., Chicago

Lincoln Park will host its annual Wine Fest, featuring tastings of wines from all around the world, live music, a variety of food and craft vendors, and more. Festivities will take place in Chicago’s Jonquil Park, and VIP tickets are $65, with General Admission at $40.

Oct. 9-10: Kohl Children’s Museum Fall Family Festival

2100 Patriot Blvd, Glenview

kohl children's museum fall fest

Grab your tickets in advance for Kohl Children’s Museum Fall Family Festival, Oct. 9-10. Tickets are $25 a person, and only $15 for members. Tickets include a kiddie train ride along a not-so-scary haunted ghost hunt path, a farm animal petting zoo, and an old fashioned cider press, where kids can make their own cider.

Oct. 10: Bank of America Chicago Marathon

They’ve trained for months, and the day is finally here: the 2021 Bank of American Chicago Marathon! Spectator information can be found on the marathon’s website, including virtual options to watch from home. You can also cheer on runners in Greektown, where they will have live music, a sign-making station, coffee and Greek pastries from 8 a.m. – 2 p.m.


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Macaire Douglas

Macaire Douglas lives in the Chicago suburbs with her husband and two sons. She proudly supports Save Abandoned Babies Foundation, a Chicago-based nonprofit organization that works tirelessly to prevent the illegal abandonment of newborns nationwide. Since its inception in 2000, more than 3,600 newborns have been safely surrendered and adopted into loving homes.