September 20, 2023

Fun Fall Activities around the New Eastside

September 20, 2023

Fun Fall Activities around the New Eastside

New Eastside

10 Fun Fall Activities

While summer is celebrated by Chicago residents, autumn brings its own thrill. The transformation of leaf colors and the onset of cooler temperatures inspire popular seasonal activities such as trips to pumpkin patches and apple picking adventures. Although not every city inhabitant has the liberty to spend an hour traveling to an orchard, there are exceptional fall activities taking place within and around the New Eastside.
10/1/2023 12pm-5pm

Oktober Family Fest

The live music event begins at noon featuring School of Rock Oak Park until 2 pm, followed by Joints Creek from 2-3pm, and The Luna Blues Machine from 3-5pm. In addition to the music, there are fun activities in store like balloon twisting, face painting by TwistiCity, and crafts with Friends of Chicago River. The event promises lots of family fun. In partnership with Temperance, 25% of their sales will be donated to the Friends of the Chicago River organization.
Every Saturday 9/30/23-10/28/23

Fall Fest on the Riverwalk

Island Party Hut is hosting Fall Fest on the Riverwalk every Saturday from September 30th - October 28th. This event offers a range of fun activities that celebrate the fall season, beyond just enjoying pumpkin-spiced lattes! It's an excellent destination for both adults seeking a relaxed time with friends and children looking for a day full of fun.

This outdoor event, set along the scenic Chicago Riverwalk, promises live music performances at two slots (1-4pm & 5-8pm), scenic hayrides on the river, fall-themed drinks including cocktails and beer, and delicious treats like apple cider donuts.

The fest features a pumpkin patch, a bounce house, and various photo opportunities, which cater to all ages, and games for added enjoyment. Please note, you must be 21 or above to drink. The event's overall ambiance aims to make guests Fall or Autumn lovers, no matter what they prefer to call this season!
Everyday in the Fall

Check out the Fall Foliage in Millennium Park and Lurie Garden

Experience fall's vibrant hues at Chicago's Millennium Park, right opposite New Eastside. The park, adorned with autumn colors near "The Bean" and in the secluded Lurie Garden, provides a four-season retreat. Venture south towards the Art Institute, surrounded by two sculpture-filled courtyards on Michigan Avenue, exhibiting stunning fall colors. Enjoy this free oasis in the city, open 6 a.m. to 11 p.m., integrating Chicago's bests—urban views, Lake Michigan's proximity, and nature—all in one location.
October 2023

Visit the Field Museum

The Field Museum, one of the world's largest history museums situated near New Eastside, boasts Greek-style architecture with gigantic pillars and offers multiple free days this fall for Illinois residents. The museum features forthcoming exhibits like Native Voices, showcasing indigenous peoples’ history via art, music, and poetry, and Wild Colors, which presents the Field Museum’s vibrant artifacts portraying nature’s color palette, along with the notable T-Rex Sue on display. Visit their website for their free days schedule in October.
Fall 2023

Take a Haunted Tour

Experience the chilling history of Chicago with two distinctive tours. Gangsters and Ghosts Tour, a walking expedition setting off from 71 E Wacker, takes you to the heart of the roaring 1920s, where you'll learn about famous gangsters like Al Capone and visit frequented haunts such as the Congress Hotel, Palmer House and Death Alley. Running parallel to this is the Chicago Hauntings Original Ghost Bus Tour, a comfortable bus ride covering spooky locations like the Chicago City Cemetery and the site of the St. Valentine’s Day Massacre, without requiring a nighttime stroll. Leaving from 520 S Michigan, easily accessible to the New Eastside, this tour operates every Saturday throughout Autumn at 7pm. Purchase your tickets now to embark on these eerie adventures.
10/21/23 6pm-8pm 

Arts in the Dark

Don't miss Arts in the Dark, a magical evening parade celebrating Halloween as the "artist's holiday." Recognized as one of the top 6 Halloween events worldwide, it's a must-see this fall! Experience a mesmerizing display of music, dance, spectacle puppets, and creative floats. Mark your calendars for October 21st and join us on State Street, Chicago, from 6-8pm. This family-friendly event is free and open to the public. Enjoy the 9th Annual Arts in the Dark Halloween Parade, featuring dazzling floats, spectacle puppets, and creative performances against the backdrop of historic State Street. See you there!
10/21/23 11am-2pm

Wag-O-Ween Pawrade & Pawty

Celebrate our furry friends at the WAG-O-WEEN PAWRADE! It's a fantastic event happening in the New Eastside that's all about dogs. Dress up your adorable pup and join us for this unique PAWRADE. Watch as they wag their tails and steal hearts while showing off their style in a costume contest hosted by Scott Darling and judged by the local door staff.

But that's not all! There are plenty of activities to keep everyone entertained, like bobbing for bones and paw painting. We'll make sure your furry friends stay hydrated with water stations and satisfy their cravings with treats throughout the day.

Put this pawsome event on your calendar because it promises to be unforgettable. The WAG-O-WEEN PAWRADE is where dogs and their humans come together for a day of doggone fun! Sign up here.
October 14-15, 2023

Open House Chicago

Open House Chicago (OHC) is a free festival organized by the Chicago Architecture Center (CAC). It offers self-guided trails showcasing the history and architecture of Chicago, along with talks, programming, and exclusive access to significant sites across the city. This year, the in-person visits will take place on one weekend, but extended programming and city-wide trails will be available throughout October. More than 30 impressive downtown buildings will participate in Open House Chicago, all conveniently within walking distance from the New Eastside area.

Pier Pumpkin Lights

Living in the New Eastside neighborhood offers residents like us the luxury of being close to Navy Pier and all its fantastic events. It's one of the reasons why our location is so desirable. And if you're a fan of the pier, you'll be thrilled to hear about their Halloween-themed decorations! This year, Navy Pier is adding a whimsical and festive touch to Halloween with their Pier Pumpkin Lights event. From October 1st until Halloween, you can immerse yourself in the autumn atmosphere and enjoy various decorations, rides, and countless photo opportunities. Explore the pier with your family and be amazed by the array of light-up pumpkins, skeletons, and other Halloween creatures. It's an event you won't want to miss!
Fridays-Sundays 9/29/23-10/29/23

Lincoln Park Zoo Fall Fest

Get ready for a wild and exciting autumn experience at Lincoln Park Zoo's Fall Fest! From September to October, this annual celebration brings the spirit of the season to Chicago with a variety of family-friendly activities. Explore the zoo's attractions, including a Fun Slide, Harvest Maze, and inflatable fun. Plus, there's so much more to enjoy, like live music, story times, and professional pumpkin carvers. Don't miss the chance to pick your own pumpkin, play in the harvest maze, and ride the slides. And the best part? This event is completely free! Make sure to mark your calendar for upcoming events such as Spooky Zoo, Haunted History Tours, and an adults-only spooky night before Halloween. New Eastside residents, this is an opportunity you won't want to miss!

Leave a Reply

Your email address will not be published. Required fields are marked *

Sign Up For Our Newsletter


New Eastside Living

Ginger Menne
737 N. Michigan Ave, Suite 1800
Chicago, IL 60611
Tel (312) 927-0852
Off (312) 216-5887
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram