Hillcrest Pumpkin Roll Raises Funds for Local Charity
Discarded pumpkins rolled down Midland Street in Little Rock as Tomfoolery Foundation raised money for Helping Hands of Greater Little Rock.
Updated on Nov. 2, 2026 in Philanthropy
The 23rd annual Hillcrest Pumpkin Roll sent discarded pumpkins down Midland Street in Little Rock on a Sunday afternoon in November. Proceeds are being directed to Helping Hands of Greater Little Rock through the Tomfoolery Foundation.
Why it matters
The event turns discarded pumpkins into a fundraiser for a local food-focused charity. Organizers estimate it will bring in about $3,000 this year, a fraction of the well over $30,000 raised last year.
Organizers estimate the event will bring in $3,000 this year, compared with well over $30,000 raised last year. The 23rd annual event's final total has not been reported.
The players
Tomfoolery Foundation
The Tomfoolery Foundation is the organization that runs the Hillcrest Pumpkin Roll and also holds the annual Great Southern Stone Skipping Championships, directing the proceeds to local charities.
Helping Hands of Greater Little Rock
Helping Hands of Greater Little Rock is a local charity that provides food to people in need in the Little Rock area.
The details
Participants line up on Hill Street and take turns rolling pumpkins down the steep Midland Street, with a golden ticket required to take a turn. Pumpkins that cross Kavanaugh Boulevard count as successful rolls, and the route ends at a stone wall where Midland meets Lee.
Timeline
Sunday afternoon in November 2026: Hillcrest Pumpkin Roll held on Midland Street.
Last year: Tomfoolery Foundation raised well over $30,000 from the event.
Philanthropy Pipeline
The 2026 roll continues a 23-year Hillcrest tradition in which Tomfoolery Foundation routes event proceeds to local food charities. The drop from last year's well over $30,000 to an estimated $3,000 this year marks a sharp departure from that pattern.
Residents who want to support Helping Hands of Greater Little Rock can plan to attend the annual Pumpkin Roll in future years. The event's smaller estimated take this year may affect how much the charity receives from this single fundraiser.
The takeaway
Community fundraisers like the Pumpkin Roll can turn a simple neighborhood tradition into direct support for local food assistance. Checking organizer updates after the event can show how much was ultimately raised.
Further reading
Explore more Philanthropy stories covering local giving efforts across Little Rock.
Source note: This article includes information reported by ArkansasOnline.
