Fall in Chicago Autumn Activities Around Rogers Park and Lincoln Park_TAWANI Property Management

Erika Davis

Sweater/hoodie weather is here – along with vibrant foliage, pumpkins, costumes, apple cider, and all things Autumn. Chicago knows how to celebrate each of the four seasons with a seemingly endless array of local activities. Here are some of our favorite ways to celebrate Fall this year: 

Decorate Your Home with Fall Plants and Pumpkins: Charmers Café’s annual Fall Plant and Pumpkin Sale is in full swing. Pick up your favorite house or garden plants and choose from an array of pumpkins in all colors and sizes. While you’re there, you can also enjoy a delicious meal or your favorite hot or cold beverage! 1500 W Jarvis Ave.

Discover Neighborhood Ghosts: Learn about Andersonville’s spooky side with the Andersonville Ghost Tour. This 1.5-mile walking tour showcases the neighborhood’s best eerie stories and favorite haunts (pun intended!). The walking path ends at Fireside Restaurant for an optional post-tour drink or meal. Tickets are $20, and there are multiple tour dates through early November. 5060 North Clark Street.

Admire the Fall Colors: Nothing says Fall like bursts of yellow, orange, and red leaves. Pop down Jean-Baptiste Pointe DuSable Lake Shore Drive to Lincoln Park to take in the vibrant Fall foliage as the season changes. The areas around the North Pond and South Pond are particularly colorful at this time of year. 2610 N Cannon Dr (North Pond location).

Get Lost in the Pumpkins: Jack’s Pumpkin Pop-up in Goose Island is the largest pumpkin-themed installation in Chicago, with over 10,000 pumpkins. Enjoy plenty of photo ops, axe throwing, fortune telling, mining for gems, and getting lost in the corn maze. You can also grab a drink at one of the full bars and fill up at the food trucks. 1265 W. Lemoyne.

Celebrate Halloweek: Why celebrate Halloween on a single day when you can celebrate it for a full Halloweek?  Blommer Chocolate Company sponsors costume-encouraged parades from 3:30-5:30 from different neighborhood spots during the week leading up to Halloween and provides bags of chocolate goodies at the end of the route. The Rogers Park parade takes place at 3:30 on 10/26. The meeting spot is Gale Elementary- 1631 W. Jonquil Terrace.

Join Fall Fest: Lincoln Park Zoo has a host of Fall activities on the docket, with family-friendly and adults-only options. The 8th annual Fall Fest returns through October 30th with pumpkin picking, Ferris wheel rides, and Autumn leaves galore. General admission is free, and optional add-on activities are available for purchase. Also on the calendar –  History tours, Adult Howl-o-ween, and Spooky Zoo – an alternative trick-or-treat event. 2001 N Clark St.

Wind Down with Weekly Wine Tastings: Picnic Wine & Provisions offers wine tastings weekly in Rogers Park. Sample four different wines for free with any purchase, and enjoy them indoors or outside on the lawn, picnic style. Every Thursday through Jan 2023 – 5:00-7:00 p.m. 7301 N Sheridan Rd.

The year-end holiday season always seems to arrive quickly. We hope you have the chance to enjoy as many Autumn activities as you can as can in the meantime!