October In Shelton: Fall Fun, Festivals & More

Fall is officially here in Shelton, and there’s no shortage of ways to make the most of it. From festivals and farmers markets to pumpkin patches, live music and other seasonal fun, October brings plenty of reasons to get out and enjoy what’s happening close to home.

Here are some events and activities happening in and around Shelton this October.

Dates, hours and other event details can change. Check with organizers before heading out.

Pumpkinseed Hill Exploration

When: Open daily, 10 a.m. to 5:30 p.m.
Where: Pumpkinseed Hill | 120 Beardsley Road, Shelton

Pumpkin hunting comes with plenty of extras at Pumpkinseed Hill Exploration at Jones Family Farms in Shelton. Along with choosing pumpkins straight from the fields or farmyard, families can tackle a one-acre mini corn maze, explore hiking trails and stop for colorful fall photo ops. Entry tickets cover many of the activities, while tractor-drawn hayrides cost extra, and reserving tickets online can save visitors money.

Legends Of Fear

When: Fridays, Saturdays & Sundays throughout October
Where: 2 Saw Mill City Road, Shelton

Those looking for a scarier side of fall can venture into Legends Of Fear at Fairview Tree Farm in Shelton, celebrating its 30th year of haunted thrills. Visitors can brave a roughly 30-minute Haunted Hayride, take on the 45-minute Hallow walking trail or buy a combination ticket to experience both attractions. Tickets are limited each night, and organizers recommend booking early since October weekends near Halloween often sell out.

Shelton Day 2026

When: Sunday, Oct. 4, 2026, 11 a.m. to 5 p.m.
Where: Veterans Memorial Park | 38 Canal Street East, Shelton

A full day of food, music and family entertainment takes over Veterans Memorial Park for Shelton Day 2026. Kids can enjoy pony rides, train rides and a three-hour bubble show while adults browse local vendors, visit food trucks and catch live performances from the Lee-Ann Lovelace Band and Eight to the Bar. The Derby-Shelton Rotary will also hold a restaurant raffle with $2,000 in gift cards up for grabs; raffle tickets are $20.

Trick Or Treat Fest

When: Saturday, Oct. 17, 2026, 10 a.m. to 2 p.m.
Where: Discovery Museum | 4450 Park Avenue, Bridgeport

Nearby in Bridgeport, Trick Or Treat Fest at the Discovery Museum gives families a full lineup of Halloween activities under one roof. Kids can arrive in costume to explore the popular Candy Trail, make hands-on crafts, meet characters and enjoy games, stage performances, music, food and other entertainment. Admission is $10, with advance tickets available online.

The Golden Ghouls

When: Saturday, Oct. 24, 2026, 12 to 3:30 p.m.
Where: Twisted Vine Restaurant | 285 Main Street, Derby

Halloween gets a Golden Girls-inspired twist at The Golden Ghouls, held at Twisted Vine Restaurant in Derby. The drag show follows Dorothy, Blanche and Rose as they try to find a missing Sophia before the Shady Pines Halloween Ball, and guests are encouraged to join the fun by dressing in their best spooky Golden attire. Tickets range from $17.50 to $25, with lunch beginning at noon ahead of the 2 p.m. show, and tickets are nonrefundable.

Looking for more things to do in Shelton this fall? Check out the Patch events calendar for more local events and activities.

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