Best events in
Sycamore

Looking for events or things to do in Sycamore, IL? Much of the community's social calendar revolves around its historic and walkable downtown district, anchored by the DeKalb County Courthouse. The scene is defined by beloved annual festivals and regular live music at local taverns, creating a classic small-town feel.

Evenings in historic downtown Sycamore often flow from dinner to live music at neighborhood spots like PJ's Courthouse Tavern or the rooftop at MVP Sports Bar.
Blumen Gardens, set in a renovated factory, provides a unique backdrop for artist markets, creative workshops, and seasonal festivals.
Family-friendly entertainment includes free summer movies at the historic Sycamore State Theatre and recreation at the Sycamore Family Sports Center.

autocomplete

Popular in Sycamore

Explore more events

Monday Parent Playgroup Sycamore

Monday • 10:30 AM + 37 more

338 Mason Ct

Check ticket price on event

Book Queeries

Tuesday • 6:30 PM + 2 more

Sycamore Public Library

Check ticket price on event

Scream Sip and Paint

Fri, Oct 16 • 6:00 PM

Shelly's Gaming & Lounge

Check ticket price on event

Sweet Treats of the Midwest

Sat, Oct 17 • 1:00 PM

DeKalb County History Center

Check ticket price on event

Brunch with Sanderson Sisters

Sun, Oct 18 • 10:00 AM

The Regale Center

Check ticket price on event

Sycamore satellite site - Brain Aging Conference

Thu, Oct 29 • 10:00 AM

DeKalb County Extension Office

Check ticket price on event

Gather and Glow

Wed, Nov 18 • 5:00 PM

NUVO Aesthetics Clinic

Check ticket price on event

Making Solutions for Blind and Low Vision

Wed, Nov 18 • 8:00 AM

DeKalb County Farm Bureau

Check ticket price on event

Monday Parent Playgroup Sycamore

Monday • 10:30 AM + 37 more

338 Mason Ct

Check ticket price on event

Book Queeries

Tuesday • 6:30 PM + 2 more

Sycamore Public Library

Check ticket price on event

Scream Sip and Paint

Fri, Oct 16 • 6:00 PM

Shelly's Gaming & Lounge

Check ticket price on event

Sweet Treats of the Midwest

Sat, Oct 17 • 1:00 PM

DeKalb County History Center

Check ticket price on event

Brunch with Sanderson Sisters

Sun, Oct 18 • 10:00 AM

The Regale Center

Check ticket price on event

Sycamore satellite site - Brain Aging Conference

Thu, Oct 29 • 10:00 AM

DeKalb County Extension Office

Check ticket price on event

Gather and Glow

Wed, Nov 18 • 5:00 PM

NUVO Aesthetics Clinic

Check ticket price on event

Making Solutions for Blind and Low Vision

Wed, Nov 18 • 8:00 AM

DeKalb County Farm Bureau

Check ticket price on event

Explore more events

Online Events

Explore more events

How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

Check ticket price on event

HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

Check ticket price on event

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

Check ticket price on event

(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg

Tue, Oct 27 • 6:30 PM EDT

Check ticket price on event

Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

Check ticket price on event

No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

Check ticket price on event

HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

Check ticket price on event

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

Check ticket price on event

(WATCH ONLINE) Dr. Jonathan Sarna with Joseph Weisberg

Tue, Oct 27 • 6:30 PM EDT

Check ticket price on event

Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

Check ticket price on event

No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

Explore more events

From nearby cities

Beginner Mahjong 101 at Harvey's Tales

Thu, Oct 15 • 11:00 AM

Harvey's Tales

Check ticket price on event

10/19 - Algonquin, IL- Dinner After Dark

Mon, Oct 19 • 6:00 PM

Cooper’s Hawk Winery & Restaurant

Check ticket price on event

Halloween Charcuterie 101 Class

Tue, Oct 20 • 6:00 PM

Riverlands Brewing Company

Check ticket price on event

Death of a Gangster Murder Mystery Night

Sat, Oct 24 • 7:00 PM

Tria Lounge

Check ticket price on event

An Evening of Music with Peter Mayer

Sat, Oct 24 • 7:00 PM

Unitarian Universalist Congregation of DeKalb

Check ticket price on event

Size Matters Handwriting Program: Proven. Practical. Measurable. Embeddable

Fri, Oct 30 • 8:00 AM

Elgin Community College Building E

Check ticket price on event

2026 First Gen Symposium

Thu, Nov 5 • 8:00 AM

Waubonsee Community College

Check ticket price on event

2026 Leggee Holiday Craft Fair @ HHS

Sat, Nov 21 • 9:00 AM

Huntley High School

Check ticket price on event

Beginner Mahjong 101 at Harvey's Tales

Thu, Oct 15 • 11:00 AM

Harvey's Tales

Check ticket price on event

10/19 - Algonquin, IL- Dinner After Dark

Mon, Oct 19 • 6:00 PM

Cooper’s Hawk Winery & Restaurant

Check ticket price on event

Halloween Charcuterie 101 Class

Tue, Oct 20 • 6:00 PM

Riverlands Brewing Company

Check ticket price on event

Death of a Gangster Murder Mystery Night

Sat, Oct 24 • 7:00 PM

Tria Lounge

Check ticket price on event

An Evening of Music with Peter Mayer

Sat, Oct 24 • 7:00 PM

Unitarian Universalist Congregation of DeKalb

Check ticket price on event

Size Matters Handwriting Program: Proven. Practical. Measurable. Embeddable

Fri, Oct 30 • 8:00 AM

Elgin Community College Building E

Check ticket price on event

2026 First Gen Symposium

Thu, Nov 5 • 8:00 AM

Waubonsee Community College

Check ticket price on event

2026 Leggee Holiday Craft Fair @ HHS

Sat, Nov 21 • 9:00 AM

Huntley High School

Check ticket price on event

Free events

Explore more events

Chair Yoga at the Library

Thu, Oct 15 • 10:30 AM + 9 more

Sycamore Public Library

Check ticket price on event

Sweet Treats of the Midwest

Sat, Oct 17 • 1:00 PM

DeKalb County History Center

Check ticket price on event

Sycamore satellite site - Brain Aging Conference

Thu, Oct 29 • 10:00 AM

DeKalb County Extension Office

Check ticket price on event

Gather and Glow

Wed, Nov 18 • 5:00 PM

NUVO Aesthetics Clinic

Check ticket price on event

Chair Yoga at the Library

Thu, Oct 15 • 10:30 AM + 9 more

Sycamore Public Library

Check ticket price on event

Sweet Treats of the Midwest

Sat, Oct 17 • 1:00 PM

DeKalb County History Center

Check ticket price on event

Sycamore satellite site - Brain Aging Conference

Thu, Oct 29 • 10:00 AM

DeKalb County Extension Office

Check ticket price on event

Gather and Glow

Wed, Nov 18 • 5:00 PM

NUVO Aesthetics Clinic

Check ticket price on event

Explore more events

Frequently asked questions about Sycamore

Where are the best spots for live music events in Sycamore?

Downtown taverns are the main hubs for live music events. PJ's Courthouse Tavern frequently has performers on the schedule, while MVP Sports Bar offers music on its rooftop, especially during its annual block parties.

What are some family-friendly things to do in Sycamore?

Sycamore offers many activities suitable for all ages. The Sycamore State Theatre hosts a free summer movie series, and the Sycamore Family Sports Center has mini-golf and batting cages for some afternoon fun.

Are there free events to attend in Sycamore?

Yes, several free community events happen throughout the year. The weekly Sycamore Farmers Market offers a lively atmosphere with music, and the historic Sycamore State Theatre presents a free summer movie series for families.

What are some good date night ideas in Sycamore?

A great date night could involve seeing a film at the Sycamore State Theatre. For something more active, consider a summer concert from the Sycamore Park District or enjoying live music at a downtown spot like PJ's Courthouse Tavern.

What major annual events take place in Sycamore?

The city is known for its large annual community gatherings. The Sycamore Pumpkin Festival each October is a major highlight, as is the Ribs, Rhythm & Brews Fest, a popular summer tradition that happens annually.

What's the food and drink event scene like in Sycamore?

The local scene features dedicated festivals and regular markets. The annual Ribs, Rhythm & Brews Fest is a popular summer event, and the weekly Sycamore Farmers Market showcases local producers and food artisans from June into late summer.

What kind of events happen in downtown Sycamore?

Downtown Sycamore is the center for most community events. The DeKalb County Courthouse lawn hosts major festivals, while the main streets are home to holiday kickoffs like Moonlight Magic and shopping events like Witches Night Out.

Where can I find outdoor events in the area?

Outdoor activities are central to Sycamore's community life. The DeKalb County Courthouse lawn hosts large festivals, the Sycamore Park District holds a summer concert series, and MVP Sports Bar organizes annual block parties.