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  • Shop Small Crawl

    Featured

    5th Annual Shop Small Crawl: Friday, November 28th-Monday, December 1st  Get ready for a shopping adventure like no other!  Join us for the Shop Small Crawl and discover the hidden gems […]

  • Walking with Santa event photo

    Walk With Santa

    Featured

    Bundle up and bring the entire family downtown Sycamore on Friday, December 5, 2025!! Join us as we welcome Santa to Sycamore. At 4pm the Sycamore Theater will be The […]

  • Santa House

    Featured Santa House
    DeKalb County Courthouse Lawn 133 W State Street, Sycamore, IL, United States

    Santa takes time off from his workshop to vacation in Sycamore during the holiday season. His “vacation home” is located on the courthouse lawn and is open for visitors starting […]

  • Santa House

    Featured Santa House
    DeKalb County Courthouse Lawn 133 W State Street, Sycamore, IL, United States

    Santa takes time off from his workshop to vacation in Sycamore during the holiday season. His “vacation home” is located on the courthouse lawn and is open for visitors starting […]

  • Sycamore Winter Chocolate Walk

    Featured
    Sycamore, Illinois

    Bring your sweet heart or just your sweet tooth to Sycamore’s Winter Chocolate Walk on Thursday, December 11, from 4-8pm.  Enjoy decadent chocolate shopping stops and a chance to win […]

  • Santa House

    Featured Santa House
    DeKalb County Courthouse Lawn 133 W State Street, Sycamore, IL, United States

    Santa takes time off from his workshop to vacation in Sycamore during the holiday season. His “vacation home” is located on the courthouse lawn and is open for visitors starting […]

  • Santa House

    Featured Santa House
    DeKalb County Courthouse Lawn 133 W State Street, Sycamore, IL, United States

    Santa takes time off from his workshop to vacation in Sycamore during the holiday season. His “vacation home” is located on the courthouse lawn and is open for visitors starting […]

  • Santa House

    Featured Santa House
    DeKalb County Courthouse Lawn 133 W State Street, Sycamore, IL, United States

    Santa takes time off from his workshop to vacation in Sycamore during the holiday season. His “vacation home” is located on the courthouse lawn and is open for visitors starting […]

  • Santa House

    Featured Santa House
    DeKalb County Courthouse Lawn 133 W State Street, Sycamore, IL, United States

    Santa takes time off from his workshop to vacation in Sycamore during the holiday season. His “vacation home” is located on the courthouse lawn and is open for visitors starting […]

  • Sycamore’s Eat Week

    Featured
    Sycamore, Illinois

    Join us for Sycamore’s Eat Week - January 19 through January 25 2026 Get ready to treat your taste buds during Sycamore Eat Week—a culinary celebration you won’t want to […]

  • Taste of Spring

    Featured
    Historic Downtown Sycamore

    Taste of Spring returns to downtown Sycamore for an evening of wine, shopping, and springtime charm!  Grab your tasting glass and your event ticket, stroll through our downtown shops, sip […]

    $35.00

  • 2026 Sycamore Community Expo & Job Fair

    Featured

    Join us for this year's Sycamore Community Expo! The Sycamore Chamber and the Sycamore Park District are teaming up to present the 2026 Sycamore Community Expo & Job Fair. THINK […]

  • CASA Color Run

    CASA Color Run Saturday, June 6th | 8:00 AM The CASA Color Run is a fun, family-friendly 5K! Walk, jog or sprint - anything is fine so long as you […]

  • Sycamore City-Wide Garage Sales

    Join us for our annual city wide garage sales! Cruise around Sycamore, June 11 through June 13 to shop our city wide garage sales. While in town stop by and […]

  • SYCAMORE STEAM SHOW

    Featured
    27707 Lukens R in Sycamore Illnois 27707 Lukens Road, Sycamore, IL, United States

    Show Attractions The Sycamore Steam Show has so many amazing attractions that you really have to just come see it for yourself! Below we’ve featured a few of the attractions […]

  • Drone shot of downtown sycamore event

    Ribs, Rhythm & Brews Fest

    Featured

    Join us on August 22, 2026! Bigger and better than ever! More ribs, beer and music! The Fest will be held August 22 from 4 pm to 10 pm downtown […]

  • Downtown sycamore chalk walk

    Downtown Sycamore Chalk Walk

    Featured

    Downtown Sycamore Chalk Walk Date: September 12Time: 10:00 AM - 4:00 PMArtist's registration opens in July! Join us for our annual Downtown Sycamore Chalk Walk, a vibrant celebration of creativity […]

  • Fall Vintage Shop Hop

    Featured

    Hop around Sycamore this Fall enjoying the Vintage Shop Hop!

  • Ladies dressed as witches for Witches Night Out

    Witches Night Out

    Featured
    Sycamore, Illinois

    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 […]