Live at PJ's Courthouse Tavern

hoppers are encouraged to visit as many businesses over the course of the four days for a chance to win gift cards. For every 5 businesses you visit and get a “punch” on your punch card is one raffle entry for a gift card. Leave your punch card at the last business you visit.  See […]

Bring your sweet heart or just your sweet tooth to Sycamore’s Winter Chocolate Walk on Thursday, December 12, from 4-8pm.  Enjoy decadent chocolate shopping stops and a chance to win one of our chocolate gift baskets filled with chocolate samplings and an array of gift certificates from our participating businesses and other fabulous prizes! Shopping […]

Calling All Dog Lovers! This Sunday, December 15, the Sycamore Santa House is going to the dogs—literally! For one hour only, from 2:30 PM to 3:30 PM, bring your furry friends to capture the paw-fect holiday photo with Santa himself! Let your pups soak up the holiday cheer, wag those tails, and join in on […]

Join us for Sycamore’s Eat Week - January 20 through January 26 2025 We are pleased to highlight our culinary excellence as well as family fun dining by offering an entire week of dining and treats at some of our finest restaurants and eateries! No coupon or ticket is necessary. Sycamore's Eat Week: LOVE WHERE […]

Join us for this year's Sycamore Community Expo! The Sycamore Chamber and the Sycamore Park District are teaming up to present the 2025 Sycamore Community Expo & Hiring Fair. THINK SPRING! TAKE A BREAK AND HAVE SOME FUN! FREE ADMISSION AND FREE PARKING! Saturday, April 5, from 11a.m. to 2p.m. at The Sycamore Community Center, […]

Enjoy an evening of wine, tasty treats, & friends in Sycamore. We look forward to hosting you during this very special evening! There's nothing like friends & folly to kick off your Spring!                                                                     Event begins at Blumen Gardens (403 Edward Street in Sycamore) […]

Join us for a classic car show, live music, food trucks, and ice cold beer! Free event in downtown Sycamore hosted by The Dirty Bird. Visit https://www.thedirtybird815.com/projects-3 for details. 

Sunday, July 25, 2025 The Fizz Ehrler Memorial Car Show comes to Downtown Sycamore once again this summer!!! Join us! Nearly 1000 cars from drag racing to street performance including Street Rods, Street Machines, Rat Rods, Custom Trucks, Race Cars, Antiques, Classics and more. The Fizz Ehrler Memorial Turning Back Time Car Show is a […]

Join us on August 23, 2025! Bigger and better than ever! More ribs, beer and music! The Fest will be held August 23 from 4 pm to 10 pm downtown Sycamore on the corner of Somonauk and Elm Streets. There will be award-winning rib vendors from across the region, craft beer, and crowd-pleasing musical entertainment! […]

Downtown Sycamore Chalk Walk Date: September 13Time: 9:00 AM - 4:00 PMRegistration Opens early August! Join us for the inaugural Downtown Sycamore Chalk Walk, a vibrant celebration of creativity and community! Artists ages 12 and up are invited to register for $25 through Eventbrite, securing their spot with a sidewalk square surrounding the DeKalb County […]

CALL THE GIRLS! CLEAN OUT THE TRUNK! HIT THE ROAD! It's the BEST. ROAD TRIP. EVER. for you and your road trip buddies!!!! Shop owners roll out the red carpet for you on Friday & Saturday, October 3 & 4. And why not spend the night and do it all over again on the next […]

Join us my pretties for a WICKED event! Grab a few of your favorite witches for a fun shopping event in Sycamore.   Your ticket will include a  souvenir goblet, spell card (list of businesses), a chance to win one of several raffle baskets, and other fabulously wicked prizes (valued at over $600), and of course a bewitching […]

The Sycamore Pumpkin Festival takes place in downtown Sycamore, Illinois, with hundreds of Pumpkins on the Historic DeKalb County Courthouse Lawn, Fall Food Vendors, Carnivals, Craft Shows, and FREE FAMILY FUN ENTERTAINMENT! Activities Wednesday – October 23rd Pumpkin Check-in – 12 noon to 9 pm Courthouse Lawn. Hosted by the Sycamore Lions. Online Entry Form – […]

The 46th Annual Sycamore Pumpkin 10K Road Race will be held on Sunday, October 27, 2024! JOIN US THIS YEAR FOR OUR SECOND ANNUAL SYCAMORE PUMPKIN 1 MILE FUN RUN! All ages welcome and registered runners/walkers will receive an exclusive Fun Run shirt and bib. This Fun Run will start on Route 64 near the […]

Watch storefront windows “come alive” as local arts, theater and dance groups perform from 6 to 8pm.  Arts and entertainment groups from all over the county will be participating.  All will be creating holiday magic with artisans, performers, dancers and musicians. The downtown Sycamore shops are once again gearing up for this year’s shopping marathon, […]