Highwood Pumpkin Volunteers

2021 Volunteer Positions

Pumpkin Carving

Three Pumpkin Carving Areas will be located at Everts Park, City Hall Park and 424 Sheridan Road (across from Buffo's).  Each areas includes pallets of pumpkins where pumpkins are stored for carving, child safe carving knives and carving tables.

Responsibilities include carving the pumpkins, and overseeing the Pumpkin Carving Stations, including staying on top of supply of pumpkins, carving knife availability, helping children bring pumpkins to the tables and directing them to place them on the pumpkin walls if needed, and general clean up of the area. You may be asked to assist with carving so there will be lots of opportunity to utilize your creativity!


This is a fun position that needs energetic people. Knowledge of bartending is a plus! Must be 21 years of age or older, and we would love volunteers who already have Basset Certification. There will be 3 bars located on the festival grounds. If you want to be assigned to the same location as your friend(s), use the same email address to sign up. Bartending at Pumpkin Fest is a great way to meet new people while having a great time!
Volunteer Sign Up for Bartenders

Scare Run 5K Course Marshals

Guide our participants safely around the run/walk route while cheering them on, diverting traffic and handing out water at water stations. The race begins at Everts Park at 6pm so please arrive by 5:30pm to familiarize yourself with the course. Bring a chair/stool, a noise maker, some music and please dress for the weather.

Totem Pole Pumpkin Painting

The Totem Pole Pumpkin Painting will be taking place at Enjoy Highwood Park (341 Waukegan Ave, on the southwest corner of Waukegan and Walker). Volunteers will be painting pumpkins to place on totem poles, as well as A-frames throughout the park. Wear clothing you won't mind getting dirty! A signed waiver is required for all volunteers.

Prelude to Skeleton Invasion

The Skeleton Invasion makes its much anticipated return to downtown Highwood! Volunteers will be responsible for the installation of skeletons around town. Be sure to bring costumes and accessories to decorate the skeletons and get your creative juices flowing! The 2020 Skeleton invasion included scenes from Wizard the Oz, Princesses & Pirates. HPHS clubs are encouraged to decorate skeletons to represent the many activities and sports offered at the high school (i.e. swim team - towels, bathing suits and swim caps; ban - instruments, uniform; theatre - costumes). A signed waiver is required for all volunteers.

Hay Ride Attendants

This year we have a horse drawn Hay Ride! You will assist the families as they pay, wait in line and load in/out of the hay ride. Must be comfortable with small children and being around horses. A signed waiver is required for all volunteers.

Mechanical Bull Attendants

This year we will have a Mechanical Bull set up at Everts Park! You will assist the families as they pay, wait in line and load on/off of the ride. Must be comfortable with small children and being around machinery. A signed waiver is required for all volunteers.

Chamber Info Booth/Celebrate Highwood Booth

There will be 2 info booths and 1 Celebrate Highwood booth at this year's Pumpkin Fest. Tasks include selling merchandise, passing out Taki's, directing people to activities taking place at Everts Park, City Hall Park, Totem Park, Pumpkin Carving Stations and Carnival. Volunteers will be contacted by the Highwood Chamber and assigned to one of the designated areas prior to the event.