The 36th edition of THE Great Pumpkin Classic 2026 — TRUMBULL, CT
Date
October 18, 2026
Location
TRUMBULL, CT
Venue
TRUMBULL HIGH SCHOOL
Start Time
8:15 AM
Entry Fee
$17.00 – $40.00
Events
5k Run or Walk ages 19 & over, 5k Run or Walk ages 18 & under, 1+ Mile Health Walk ages 19 & over, 1+ Mile Health Walk ages 18 & under, Kids Fun Runs- ages 12 & under
Includes
Long sleeve T-Shirt | long sleeve T-Shirt | T-Shirt
The Great Pumpkin Classic is a running and walking event held in Trumbull, Connecticut, offering 3K and 5K distances. Now in its 36th edition, the race takes place on October 18, 2026, starting at 8:15 AM from Trumbull High School. Entry fees range from $17 to $40 depending on registration timing and participant category. The early morning start time makes it accessible for athletes planning to explore the area or travel later in the day. Whether you're training for fall races or looking for a local community event, this established classic provides a straightforward option with flexible distance choices to fit different fitness levels and goals.
From the Race Organizer
WELCOME TO THE 36th CONSECUTIVE YEAR OF THE GREAT PUMPKIN CLASSIC!!! PLEASE HELP US CELEBRATE OUR AMAZING EVENT- STARTED IN 1991 BY OUR RACE DIRECTOR MARTY SCHAIVONE - A BIOLOGY TEACHER AT THS (1977-2012) It's difficult to remember that far back - none of us were thinking how long this 5k would last. But 349 people started on a journey that has continued to raise money for the Trumbull High Scholarship Foundation for 35 years. Marty has retired from THS, a lot has changed, but the reputation built over 3+ decades is solidly in place. We are planning a party and we hope you'll be part of it. Our food has always been a large part of the attraction. Back again- PLASKO’S Farm Cider Donuts will also be with us for your enjoyment! Village Bagels with pumpkin mini bagels. And lots more snacks. WE ORDERED 450 SHIRTS & sold out last year so don't wait. Sign up fast and have a chance for our long sleeve beauty! Guaranteed sizing ends 10/4, after that ‘as available’ Shirt color to be determined by our professional shirt color picking team. Fabric and colors may also depend on inventory, tariffs and what's on sale. OUR NEW 2026 PRESENTING SPONSOR is RURAL FUELS of Monroe CT Locally Trusted & Family Operated https://www.rural-fuels.com/save-now Committed to fueling homes, and now runners, for over 75 years! OUR GOLD LEVEL 2025 SPONSORS *My Smile Orthodontics https://www.mysmilect.com/ *River Road Pediatric Dentistry https://www.riverroadkids.com/ *Link Crew - Trumbull High School *ODIN Capital Partners *Anonymous!! Supporting Sponsors 2025 * Refine Fitness Trumbull . *Stop & Shop- Trumbull In Kind Partners 2025 PLASKO'S Farm and Creamery NEW AMRITA Protein bars - https://www.amritahealthfoods.com/ AWARDS SPONSORS *Trader Joes Fairfield- 'Grand Prize Table' *Marathon Sports of Fairfield - gift cards It’s 2026 and for the 36th time we will be hosting THE Great Pumpkin Classic 5K Run! Last year the Great Pumpkin was blessed with a beautiful Fall day, and we had a blast! We have had a race every year since 1991. Even in Covid 2020 we were able to host the “Pumpkin Reboot” in November to celebrate our 30th year! More than 20 people of the 349 finishers from our first GPC in 1991 joined us for the historic occasion. Last year many returned again to celebrate our 35th ! Our 5k course remains the same as the last six years. This route is very much like our original course from 1991 with a bit of an uphill the first mile. See the map link and details below. The untimed Walk For Health will again be an easy 1.7mi. The Kids Fun Run will be on the nice, flat track! And as good as ever thanks to Jon Dizney, Donna Cramond and their team. The run, walk & kids committees, sponsors, and volunteers truly appreciate you joining us as we return to THS. You will be helping to add to our proceeds which have totaled over $340,000 in scholarships since our start in 1991. Our charities include the Trumbull High School Scholarship Foundation and the Trumbull Schools PTSA . Please help us and donate any extra you can for our students that need the help of our foundation! PLEASE PRE REGISTER ONLINE ASAP to avoid race day stress and TO ENSURE SHIRT SIZING & AVAILABILITY. Online registration only on event day - it ends five minutes before the start . EVENT FEES : The 5k is a 3.1mi distance and a computer chip-timed event. Awards only for this event. Participants of all abilities are welcome to run or walk this event. REG IS ONLINE ONLY. EVEN RACE DAY IF WE ARE NOT SOLD OUT. (we pay all tariffs) 5K 19 & over 18 & under 2/14 - 4/30 $28 $20 (just about 1991 pricing!) 5/1 - 7/31 $31 $23 8/1 - 10/4 $34 $26 10/5 - 10/11 $37 $28 10/12 - 10/18 $40 $30 NO PAPER/NO CASH on site on event day 1.7 MILE WALK - this event is not timed- there are no awards 2/14 - 4/30 $28 for 19 & over, $20 for 18 & under 5/1 - 10/4 $31 / $23 10/5-10/18 $35 / $25 REG IS ONLINE ONLY. NO PAPER or CASH KIDS FUN RUNS - varying distances and not timed. Kids get a shirt, finishing medal & snack!! 4/4-10/11 $17 10/12-10/18 $20 Note- shirts for the kids run could sell out ahead of time! CALENDAR 2/14 Registration opens 10/4 Guaranteed shirt sizing ends . After that ‘as available’ and we could definitely run out! 10/17 Early pickup 8:30-10:30am in the front (right side) foyer of Trumbull High School 10/18 EVENT DAY - ALL REG IS ONLINE ONLY - NO PAPER & NO CASH 7:30 am Pickup & late reg online only for the 5k & walk - in the THS cafeteria 7:45 am Pickup & reg for the kids runs - on the track at the football field 8:10 am Kids Runs - various distances for age groups on the THS track 8:50 am Introductions, THS Men's & Women’s Ensemble sing the National Anthem START LOCATION - On the driveway of the 'A House' side of the building- near the big lot. Look for the start banner! 9:00 am GREAT PUMPKIN CLASSIC 5K & untimed 1.7mi Walk START 9:30 am POST RACE Party - FEATURING PLASKO'S FARM APPLE CIDER & PUMPKIN DONUTS! Plus more Snacks, fruits & fluids OUTSIDE NEAR THE START/Finish 10:00 am 5K Awards
Hotels Near This Race
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The 36th edition of THE Great Pumpkin Classic 2026 — TRUMBULL, CT
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Race Travel Insurance
Don't forget travel insurance for October 18.
You've trained for months and booked a trip to TRUMBULL, CT.
A pre-race injury, a delayed flight, or a family emergency can derail the whole thing.
Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it,
and may cover medical costs if something goes wrong on the course. Plans typically only run
5-7% of your total trip cost — and running events are covered under standard plans with no
additional coverage needed.
Trip cancellation up to 100% of prepaid costs
Running events covered under standard plans — no add-ons needed
Trip interruption up to 150% of non-refundable costs
When is The 36th edition of THE Great Pumpkin Classic 2026 — TRUMBULL, CT?
The 36th edition of THE Great Pumpkin Classic 2026 — TRUMBULL, CT takes place on October 18, 2026. The race is held in TRUMBULL, Connecticut.
Where is The 36th edition of THE Great Pumpkin Classic 2026 — TRUMBULL, CT held?
The 36th edition of THE Great Pumpkin Classic 2026 — TRUMBULL, CT is held at TRUMBULL HIGH SCHOOL in TRUMBULL, Connecticut.
Where can I find hotels near The 36th edition of THE Great Pumpkin Classic 2026 — TRUMBULL, CT?
RaceHotelFinder shows hotels sorted by distance from the race venue in TRUMBULL. Use the map or list view on this page to compare options and book race weekend accommodation.
