3 things to do in Cleveland in October
October in Cleveland is often painted in warm fall colors, with reds, oranges and yellows. Here at Case Western Reserve University, a different hue marks the month: CWRU Blue. The university’s annual Homecoming and Reunion Weekend will be held Oct. 8-11. During the spirited festivities, students, alumni, faculty, staff, families and friends of the university will gather to celebrate all things CWRU.
Whether you’ve had some of the hallmark events—such as the parade, tailgate and football game—on your calendar for months or you’re new to CWRU, make sure to check out the full schedule to show your Spartan pride.
If you’re looking for more to do during the month, Cleveland has plenty more to offer, including some traditional fall-centric festivities. We pulled together a few suggestions to get you started, but be sure to visit the Destination Cleveland website for more ideas.
Cleveland Pickle Fest
Oct. 3
Cleveland has a festival to celebrate just about every type of food, including pickles. Cleveland Pickle Fest, held by Greater Cleveland Volunteers, will be held from 11 a.m. to 6 p.m. Oct. 3 on Mall C downtown.
At this event, everything is pickle-flavored—from your pizza to your ice cream.
Don’t like pickles? There’s plenty more to do during this event. The day kicks off with a 5K race and continues with live music by Böaterhead and Jasmin Jeanise throughout the day. And while pickles are a major draw for this event, it ultimately serves as a celebration of volunteerism in Cuyahoga County.
General admission is $10, and children ages 5 and under are free. Register for the 5K for $45, which includes admission to the festival.
Learn more about the festival and get your ticket.
17th Chagrin Documentary Film Festival
Oct. 6–12
Each year, the Chagrin Documentary Film Festival celebrates the art form of documentary filmmaking.
In its 17th year, the 2026 festival includes a nod to the America 250 celebration with films and special events recognizing United States history.
Screenings will be held at venues across Chagrin Falls. In addition to the film showings, there will be filmmaker discussions and panels. Following in-person screenings Oct. 6–12, the festival will continue in a virtual format Oct. 13–19 with on-demand streaming.
Review the documentary lineup and purchase tickets.
Symphony at Sunset: An Autumn Encore
Oct. 11
Take in the views of Downtown Cleveland and Lake Erie set to a backdrop of classical music during an encore performance of the Symphony at Sunset series.
Beginning at 3 p.m. on Oct. 11, guests can come to Voinovich Park for mini pumpkin painting, yard games, food trucks and crafts. Then, from 5 to 6:30 p.m., OPUS 216 will perform.
This free event is hosted by Downtown Cleveland, Inc. with support from the City of Cleveland.
