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Sycamore Pumpkin Fest

Name: Sycamore Pumpkin Fest
Start: 2026-10-21T00:00:00-05:00
End: 2026-10-25T23:59:59-05:00

October 21 – October 25

Image of painted pumpkins on the lawn at the 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 21st
- 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/2026_sycamore_pumpkin_fest/shop/home
- West School Organization (WSO) – Pumpkin Fest tote bags and light up pumpkin wands in front of Adventure Sprouts 4 pm – 9 pm
- Tumblers, Bags, Umbrella’s – Bethel Girls Ministry at Bethel Assembly of God
Thursday – October 22nd
- Kiwanis Prayer Breakfast – United Methodist Church, 160 Johnson Avenue. 7 am to 9 am
- Trick or Treat Event – Along State St. 4 pm to 6 pm. 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/2026_sycamore_pumpkin_fest/shop/home
- Tumblers, Bags, Umbrella’s – Bethel Girls Ministry at Bethel Assembly of God
Friday – October 23rd
- 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.
- Royal Rangers – Buttons, Patches, Hats, and Stickers in front of Blue moon Bikes 4pm – 8pm
- 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/2026_sycamore_pumpkin_fest/shop/home
- Tumblers, Bags, Umbrella’s – Bethel Girls Ministry at Bethel Assembly of God
- Pumpkin Ball – hosted by the Girl Scouts 5 pm at the Regale Center
- West School Organization (WSO) – Pumpkin Fest tote bags and light up pumpkin wands in front of Adventure Sprouts 4 pm – 9 pm
- Girl Scouts of Northern Illinois – Girl Scout merchandise, fidgets, slime, poncho toys and more 3pm-8pm located on South Maple
Saturday – October 24th

SATURDAY ENTERTAINMENT SCHEDULE
- 10:00 AM — Magic Matt Stage Show
- 11:00 AM — Lumberjack Show
- 12:00 PM — Magic Matt Stage Show
- 1:00 PM — Lumberjack Show
- 1:30 PM — Magic Matt Stage Show
- 2:00 PM — Lumberjack Show
- 2:30 PM — Magic Matt Stage Show
- 3:00 PM — Lumberjack Kids Camp
Happening throughout the day:

Magic Matt — Balloon animals & strolling magic
DJ Dance Party — Music, dancing & fun between shows
Face Painting — Presented by the Sycamore High School Art Club

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

St. Mary’s Youth Group – Baked Goods, snacks, caramel apples, beverages 10am-6pm

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.

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

Pumpkin Festival Flags – ABC Preschool, in front of Paulson Appliance. 10am – 2pm.

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

Sycamore Fire Buddies – T-shirts, sweatshirts, hats, tumblers 9am-6pm in front of Paulsons

Royal Rangers – Buttons, Patches, Hats, and Stickers in front of Blue moon Bikes 10am – 6pm

Shirt Sales by Rotaract – North Maple Street 11am-9pm Preorder by October 15th to guarantee your shirt at https://stores.inksoft.com/2026_sycamore_pumpkin_fest/shop/home

West School Organization (WSO) – Pumpkin Fest tote bags and light up pumpkin wands in front of Adventure Sprouts 8 am – Noon

Tumblers, Bags, Umbrella’s – Bethel Girls Ministry at Bethel Assembly of God

Girl Scouts of Northern Illinois – Girl Scout merchandise, fidgets, slime, poncho toys and more 9am-5pm located on South Maple

Sunday – October 25th

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/2026_sycamore_pumpkin_fest/shop/home

Tumblers, Bags, Umbrella’s – Bethel Girls Ministry at Bethel Assembly of God

Craft & Vendor Shows: Sycamore Music Boosters Autumn Craft/Treasures Market 427 Spartan Trail 9am-3pm.

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

Royal Rangers – Buttons, Patches, Hats, and Stickers in front of Blue moon Bikes 9am – 4pm

Pumpkin Festival Flags – ABC Preschool, in front of Paulson Appliance. 10am – 2pm.

Girl Scouts of Northern Illinois – Girl Scout merchandise, fidgets, slime, poncho toys and more 9am-5pm located on South Maple

Girl Scout Troop 353 – Pumpkin Festival Blankets 9am-5pm located on South Maple

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