2025 Trumbull Fall Fun Guide: Fall Festival​, Marching Band Fall Classic​ And More

TRUMBULL, CT — The autumnal equinox on Monday, Sept. 22, signals the official arrival of fall, but the season is already in full swing in the Trumbull area with events such as corn mazes, hay rides, fall festivals and harvest events.

Sunny days and crisp evenings are perfect for outdoor fun. One can’t-miss event is the Trumbull Fall Festival, which will be held Oct. 26 on the Trumbull Town Hall Green.

But that’s just the beginning of fun activities taking place over the next couple of months.

See also: Where To Pick Apples Around Trumbull: 2025 Guide

Are you planning an event this fall? Feature it so nearby readers see it all across Patch — including in roundups like this!

Below, find the 2025 Patch Guide to Fall Fun in the Trumbull area:

• Trumbull Fall Festival (Trumbull)

Join Trumbull Parks & Recreation at the Trumbull Town Hall Green for a fun fall day of music, games and crafts.

• Trumbull High School Golden Eagle Marching Band Fall Classic (Trumbull)

The Trumbull High Fall Classic is an exhilarating day of music and showmanship where 16 bands and color guard teams from across the region compete against each other.

• St. Joseph High School Fall Open House (Trumbull)

Explore the endless opportunities awaiting you at St. Joseph High School’s Fall Open House on Sunday, Sept. 28 from 1 p.m. to 3 p.m. As CT’s largest co-ed, Catholic college preparatory school, St. Joes offers an experience designed to help you unlock your full potential.

• Apple Festival/Vendor Fair at Lordship Community Church (Stratford)

The event is expected to feature craft and business (direct sales) vendors, flea market/tag sale vendors, food, live music, a bounce house, raffle prizes, red apple lawn sign sponsors, and a fundraiser.

• Annual Fall Fair (Derby)

The annual fall fair will be held at the Derby Senior Center.

• Commodore Hull Thanksgiving Day 5k Road Race (Shelton)

Be part of a Valley tradition! The Commodore Hull Thanksgiving Day 5K Road Race kicks off at 8 a.m. in downtown Shelton, winds through Derby, and loops back to Shelton.

• Bethany Harvest Festival (Bethany)

Enjoy food trucks, entertainment, crafters, vendors, animals, kids activities and more.

• Harvest Moon Festival (Naugatuck)

Join the Naugatuck Historical Society at this year's Harvest Moon Festival, hosted by Troop 102 Scouts BSA!