2025 Shelton-Derby Fall Fun Guide: 5k Road Race, Annual Fall Fair And More

SHELTON-DERBY, CT — The autumnal equinox on Monday, Sept. 22, signals the official arrival of fall, but the season is already in full swing in the Shelton-Derby 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 Commodore Hull Thanksgiving Day 5k Road Race, which kicks off in downtown Shelton, winds through Derby, and loops back to Shelton.

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

See also: Where To Pick Apples Around Shelton-Derby: 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 Shelton-Derby area:

• 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.

• Annual Fall Fair (Derby)

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

• Olde Derby Pub Crawl (Derby)

The Derby 350 Pub Crawl will offer participants "an unforgettable evening filled with fun, friends and fantastic local pubs."

• 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.

• Harvest Moon Festival (Naugatuck)

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

• Lantern Tours at Grove Cemetery (Naugatuck)

Take an evening stroll through the beautiful Grove Cemetery—if you dare.

• Bethany Harvest Festival (Bethany)

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