Highwood Pumpkin Fest

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Nature & SeasonHighwood
DatesDates TBA · Usually OctoberCheck locally before booking
DurationAutumnEstimate from available data
Crowd-Public scale varies
Best forSeasonal rites, water traditionsHighwood's pumpkin festival is built around
LanguageLocal language; English access variesCurrency: USD
CategoryNature & SeasonFestival type
The story

Highwood Pumpkin Fest in Highwood

The Great Highwood Pumpkin Fest is a free, family-oriented fall street festival held over three days in early October in downtown Highwood, Illinois, a small North Shore suburb near Highland Park. Organized by the nonprofit Celebrate Highwood, it fills City Hall grounds, Everts Park, and the Metra station lot with live music, a carnival, pumpkin carving, and costume contests, with proceeds benefiting a rotating local charity partner each year.

Its pumpkin spectacle and North Shore setting make it a good seasonal row.
Your trip starts here
What is special

The part that makes it specific.

01

The place changes

Highwood's pumpkin festival is built around two giant pumpkin walls and community carving stations set up in front of City Hall, plus a month-long run of fall-themed skeleton displays nicknamed the Skelebrity Walk of Fame that appear on downtown streets weeks before the festival itself

02

The mystery stays covered

A kid-scaled Pumpkin Speedway lets children take the wheel of micro NASCAR-style race cars sponsored by local businesses

03

The city starts moving

The festival charges no entry fee and welcomes leashed dogs, and it closes with a lighting ceremony for the pumpkin wall

04

The water draws everyone in

Because Highwood's downtown has long been known for its concentration of Italian and other North Shore restaurants, the festival doubles as a showcase for the town's dining scene, with restaurants staying open through the weekend crowds

Traditions & symbols

The language of the festival.

What moves first

Living ritual

The town-wide skeleton display

Water and renewal

Living ritual

known as the Skelebrity Walk of Fame

The sacred route

Living ritual

is Highwood's signature pre-festival ritual

The local code

Living ritual

with decorated skeletons appearing on porches and storefronts beginning weeks before the main event to build anticipation

Tradition 5

Living ritual

The Saturday-night lighting of the giant pumpkin wall functions as the festival's ceremonial centerpiece each year

Tradition 6

Living ritual

Costume contests for children and for pets

Tradition 7

Living ritual

run as separate judged categories

Tradition 8

Living ritual

and a community pumpkin-carving station outside City Hall are recurring elements attendees return for annually

Before you go

Essential information

When to go

Dates TBA · Usually October

Getting around

Metra can help avoid parking.

What to wear

Casual fall attire works best: jeans, closed-toe shoes for walking on pavement and grass, and a jacket or sweater, since early October evenings on Lake Michigan's North Shore can turn cool...

Safety

Keep distance from unsafe water edges and follow local crowd or weather warnings.

Where to stay

Highwood

Tickets/cost

Public water rituals are often open, but boat, viewing, or activity access may be paid.

Language/currency

USD

Family friendly

unknown

Interactive map42.20 N, 87.81 WOpen in Google Maps

Highwood, IL

TransportMetra can help avoid parking.
Stay areaHighwood

Your Trip Starts Here

External travel services to turn the plan into a trip — each opens in a new tab.

How to get thereRoutes, times and prices to Highwood via local transport.Search routesFind a place to stayStays near Highwood, close enough for the event-day route.Browse staysFind flightsCompare fares into the nearest practical airport for October.Compare faresFestival gearCasual fall attire works best: jeans, closed-toe shoes for walking on pavement and grass, and a jacket or sweater, since early October evenings on Lake Michigan's North Shore can turn cool after sunset. Costumes are welcome and encouraged for the children's and pet costume contests.Shop the kitCheck visa requirementsSee whether you need a visa for United States and apply online.Check entry rulesTravel insuranceCover for trip hiccups, gear and health on the road.Get covered

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FAQ

Quick answers.

When is Highwood Pumpkin Fest?

Highwood Pumpkin Fest is listed for October · Autumn. Always re-check the official or local source close to travel.

Where does Highwood Pumpkin Fest take place?

The festival is listed in Highwood, United States. The map coordinate is a planning reference, not a guarantee of a ticket gate or exact venue.

How long should I plan for?

Autumn is the listed festival span. Add time for arrival, local transport, queues, and any route changes during the event.

Is a source linked?

Official source linked. Eventisimus separates source confidence from travel suggestions, so check final details before booking.

Where exactly is it?

Highwood, IL

Is it family friendly?

unknown

Sources and editorial review

About this guide

This guide is independently written by Eventisimus using publicly available information, official event and organiser sources where available, local tourism references, and additional editorial research. Eventisimus is not the official organiser of this festival and is not affiliated with it unless explicitly stated.

Festival dates, schedules, ticket conditions, access rules, and local arrangements can change. We aim to present useful and accurate information, but travelers should confirm important details with the official event source before booking transport, accommodation, or tickets.

Found something inaccurate or outdated? Email hello@eventisimus.com with the festival page link and the correction.

Official URLcelebratehighwood.org
Organizer accessAre you the organizer? Claim this listing →
SourceSource link available
Listed datesDates TBA · Usually October
Source statusOfficial source linked
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