Sycamore Pumpkin Fest

Experience one of Illinois’ favorite fall traditions at the Sycamore Pumpkin Festival! Stroll through downtown filled with hundreds of decorated pumpkins, enjoy carnival rides, craft shows, delicious festival food, live entertainment, and fun for the whole family.

2026 Activities

• Wednesday – October 22nd

  • Pumpkin Check-in – Courthouse Lawn. 12 noon to 9 pm Hosted by the Sycamore Lions. Online Entry Form – https://form.jotform.com/212408041839049
    Paper forms will be available during check in.
  • Opening / Giant Cake Cutting Ceremony – North Maple Street adjacent to the Courthouse. 5 pm Cake compliments of HyVee.
  • Shirt Sales by Rotaract – North Maple Street 4pm-9pm Preorder by October 15th to guarantee your shirt at https://stores.inksoft.com/2025_sycamore_pumpkin_fest/shop/home

  Thursday – October 23rd

  • Kiwanis Prayer Breakfast – United Methodist Church, 160 Johnson Avenue. 7 am to 9 am
  • Trick or Treat Event – Along State St. 4pm to 6pm. Hosted by the City of Sycamore.
  • Pumpkin Celebrations –  Sycamore Public Library, 103 E. State St. All things PUMPKIN! Crafts, games, treats and other fun. 4 pm to 8 pm
  • Shirt Sales by Rotaract – North Maple Street 4pm-9pm Preorder by October 15th to guarantee your shirt at https://stores.inksoft.com/2025_sycamore_pumpkin_fest/shop/home

  Friday – October 24th

  • Teen Carnival – Sacramento & State. 3 pm to 10 pm ($35 unlimited ride special 4 pm to 8 pm)
  • Kiddie Carnival (Pre-5th Grade) – Somonauk & Elm. 3 pm to 10 pm ($35 unlimited ride special 4 pm to 8 pm)
  • Craft Show – United Methodist Church. 160 Johnson Ave. 11am-5:30pm.
  • Pumpkin Festival Flags – ABC Preschool, in front of Paulson Appliance. 9am – Noon.
  • Shirt Sales by Rotaract – North Maple Street 4pm-9pm Preorder by October 15th to guarantee your shirt at https://stores.inksoft.com/2025_sycamore_pumpkin_fest/shop/home
  • Owala Drink Tumblers – Bethel Girls Ministry in North Food Court

  Saturday – October 25th

  • The Frog Lady (Sponsored by Syngenta)
    North Food Court, 11 am
  • Magician Rob Thompson (Sponsored by Leeward Renewable Energy)
    North Food Court, 1 pm
  • Performing Arts Academy (Sponsored by Syngenta)
    North Food Court, 2:30 pm
  • Owala Drink Tumblers – Bethel Girls Ministry in North Food Court

  Regular Saturday Events

  Teen Carnival (Sacramento & State) & Kiddie Carnival (Somonauk & Elm) – 12 noon to 10 pm ($30 unlimited ride special 12 noon to 4 pm / $35 unlimited ride special 5 pm to 9 pm)

  Sycamore Rotary Pancake Breakfast  – St. Mary’s Parish Activity Center, 312 Waterman St. 7 am to 11 am

  Dog Treats, Costumes, T-Shirts – Tails Humane Society, in front of Taxco. 9 am to 4 pm

  Craft & Vendor Shows:

  • ACS/Cornerstone Campus, 355 N. Cross St. 9am-5pm
  • United Methodist Church. 160 Johnson Ave. 9am-4pm.
  • Sycamore Music Boosters Autumn Craft/Treasures Market 427 Spartan Trail 9am-5pm.

  Giant Pumpkin Trophy Presentation – Sycamore Lions’ Club, Courthouse Lawn. 10 am

  Historic Homes Tour – DeKalb County History Center
  $25 per person. 10 am to 4 pm
  Advance tickets can be reserved online at dekalbcountyhistory.org.  ALL participants must check in at the History Center, the day of the event, 1730 N. Main St.

  Face Painting – Sycamore High Art Club, at the Kiddie Carnival. 10 am to 2 pm

  Pumpkin 4-Person Golf Scramble – Sycamore Golf Course, 940 E. State St. 11 am Registration information (815) 895-3884

  Pie-Eating Contest – Kiwanis Club, Courthouse Lawn. 4 pm

  Sycamore Fire Buddies – T-shirts, sweatshirts, hats cups and stickers

  Shirt Sales by Rotaract – North Maple Street 11am-9pm Preorder by October 15th to guarantee your shirt at https://stores.inksoft.com/2025_sycamore_pumpkin_fest/shop/home

  Sunday – October 26th

  Sycamore Chamber 10K Pumpkin Run – Sycamore Armory. Race Starts at 8:30 am at the  Sycamore Pumpkin Run

  Shirt Sales by Rotaract – North Maple Street 11am-1pm Preorder by October 15th to guarantee your shirt at https://stores.inksoft.com/2025_sycamore_pumpkin_fest/shop/home

  Owala Drink Tumblers – Bethel Girls Ministry in North Food Court

  Craft & Vendor Shows: Sycamore Music Boosters Autumn Craft/Treasures Market 427 Spartan Trail 9am-2pm.

  Teen Carnival (Sacramento & State) & Kiddie Carnival (Somonauk & Elm) – 12 noon to 5 pm ($30 unlimited ride special from 12 noon to 4 pm)

  Opportunity House and Dirty Bird – 11am-3pm

  Pumpkin Festival Parade – Somonauk – Elm – California – State & Main Streets.  Parade kicks off at 1 pm. Parade Map Sponsored by Ideal Industries, Sycamore Music Boosters, DeKalb Sycamore Chevy / Buick / GMC and Upstaging.

For more info visit https://www.sycamorepumpkinfestival.com/