Trumbull Family-Friendly Fall Activities 2026

Get lost in the "It's a Bug's Life" themed corn maze at Wells Hollow Creamery. Brave the Flashlight Maze on select evenings for a thrilling, dark adventure. During the day, enjoy the "Corn Maze Challenge" and visit the farm animals....

Get ready for a spooktacular Halloween celebration at the Walnut Beach Halloween Parade! This family-friendly event features candy, costumes, and dancing with a DJ. Don your best costume for a chance to receive free ice cream from Walnut Beach Creamery,...

Bring your furry friends to the Walnut Beach Arch for a delightful Halloween Pet Parade and Contest. Dogs can strut their stuff in their most creative, scariest, or funniest costumes for a chance to win prizes. A panel of judges...

Get ready for a spook-tacular day of Halloween family fun at the shore! Dress up in your best costume and join the festivities at Walnut Beach. They'll have trick-or-treat stops throughout the district, enchanting horse and carriage rides, live entertainment,...

Immerse yourself in the autumn spirit at Jones Family Farms' Pumpkin Season. Wander through vast pumpkin fields to select your perfect gourd, or enjoy a scenic hayride through the picturesque landscape. Discover fun photo opportunities, educational displays, and a charming...

Join the Downtown Milford Business Association for their annual Hall-O-Weekend Fall Festival, a free, not-so-scary Halloween celebration. Families and children can enjoy a weekend of costumes, adventures, and treats. Activities include an outdoor movie night, a costume parade, kids' yoga,...

Join the Milford Trick or Trot for a festive Halloween celebration featuring a 5K run/walk and an outdoor family movie night. This community event supports the Beth-El Center, helping to combat hunger and homelessness. Don your best costume for a...

Lace up for the 14th Annual Milford Trick or Trot 5K Run/Walk! This festive event supports The Beth-El Center, aiding those experiencing homelessness. Participants can choose the 5K run/walk or the free Kids Halloween Dash. Don your best costume for...

Experience an authentic farm adventure at Warrup's Farm this fall. Visitors can pick their own pumpkins straight from the vine, enjoy a classic hayride, and browse the farm stand for local apples, cider, honey, gourds, and more. It's a perfect...

Join the ultimate Halloween celebration at Chuck E. Cheese Orange for their Boo-tacular event! Enjoy safe, nightly trick-or-treating with Airheads® candy, spooky shows, and delicious seasonal treats. Kids in costume receive 500 free tickets, and special Halloween menu items like...

Get lost in the expansive seven-acre corn maze at Castle Hill Farm, featuring a new, unique design each year. Navigate through 30 game signs, or take a break at the observation deck. Special 'Flashlight Maze' nights offer a thrilling after-dark...

Discover the charm of the Seymour Pumpkin Festival, a beloved tradition since 1965. This family-friendly event offers a delightful day out with a vibrant mix of craft vendors, diverse food options, live entertainment, and engaging activities. Explore themed areas like...

Stepping Stones Museum for Children hosts the annual Beasties and Besties Halloween Bash, a spooktacular event for all ages. This museum-wide haunted festival features a Monster Mash dance party, classic carnival games, and creative craft stations like pumpkin decorating and...

Discover the vibrant culture of Norwalk, CT at the NICE Festival on Saturday, October 4, 2025. This free, family-friendly event at Oyster Shell Park features two stages with over 24 live performances, showcasing diverse traditions and genres. Explore over 50...

Experience a unique Halloween celebration at the historic Shubert Theatre with a free family fun day. Patrons can enjoy a self-guided backstage tour, complete with trick-or-treat stations along the way. Children are encouraged to wear their costumes for the festivities.

Norwalk's Washington Street comes alive for the annual Halloween Nightfair, a vibrant celebration transforming the area into a festive hub. From afternoon delights like pumpkin painting and a Trick or Treat Trail to evening entertainment and glowing lights, the event...

Join families for the 33rd Annual Halloween on the Green, a spirited community event featuring a children's costume parade with prize categories for originality, scariness, and cuteness. Attendees can enjoy local vendors, music, a photo booth, and kid-friendly activities. Goodie...

All aboard 'The Husking Bee' for a delightful fall adventure! This beloved annual event offers families a charming 20-minute train ride to a special pumpkin patch. Passengers can pick out their own pumpkin, enjoy local apple cider and cookies, and...

The New Canaan Halloween Block Party is a cherished annual event where the town's youngest residents and their families gather to celebrate Halloween. Held on Elm Street, this block party provides a safe and exciting environment for children to show...

Experience a charming fall adventure at the Shore Line Trolley Museum's Pumpkin Patch. Ride historic trolleys through scenic salt marshes, observe local wildlife, and explore a collection of vintage transit vehicles. This unique event offers a glimpse into the past...

Embark on a delightful Halloween adventure at Heckscher Farm, a special members-only event. Children aged 3-10 can explore the farm, solve a fun Halloween riddle by visiting themed stations, greet beloved animal friends, and create a craft. Upon completing the...

Join the annual Boomer's Boo Bash, a beloved Halloween celebration hosted by Quinnipiac University for the local communities. This family-friendly event invites local businesses, student organizations, and student-athletes to share in the festive fun on the university's Quadrangle. Attendees can...

Get ready for a Spooktacular Oktoberfest at Trailside Nature Museum! This annual event combines Halloween thrills with fall festival fun. Kids can enjoy trick-or-treating, a costume contest, and crafts, while everyone can experience hayrides and engaging presentations. The Oktoberfest section...

Get ready for a spooktacular time at the Fourth Annual Stamford Moms Halloween Candy Crawl! Families can enjoy a free event filled with trick-or-treating at participating retailers and vendor tables. Kids can meet beloved characters like Elmo and Cookie Monster,...

Experience the charm of Cheshire's "Pumpkin Church" as St. Peter's Episcopal Church transforms into a vibrant pumpkin patch each September and October. This cherished 20-year tradition offers a fantastic opportunity to select the perfect pumpkin while supporting indigenous growers and...

Experience the magic of autumn at Harvest Moon Farm and Orchard's Fall Festival. This two-month celebration offers a delightful escape with live country music, a sprawling pumpkin patch, and delicious seasonal treats. Families can enjoy apple picking, hayrides, and a...

Step into a world of Halloween enchantment at the Suffolk County Vanderbilt Museum. This historic estate transforms into a hub of seasonal activities, offering a blend of spooky fun and educational exploration. Discover the mysteries of the cosmos at the...

Bishop's Fall Festival offers a quintessential autumn experience with apple picking, a unique New Haven Pizza-themed corn maze, and a vibrant pumpkin patch. Families can enjoy a wide array of activities, including jump pads, a corn pit, and pedal carts,...

Visit Harris Hill Farm for their annual pick-your-own pumpkin patch, open weekends throughout October. They offer a fantastic selection of large, jack-o'-lantern style pumpkins, alongside a variety of other fall crops like butternut squash, spaghetti squash, and decorative gourds. It's...

Join the Guilford Free Library for a Spooktacular on the Green, featuring engaging spooky stories for children and tweens. This family-friendly event, part of the town's annual Halloween celebration, also includes live music, performers, and a fun trunk-or-treat. All ages...

Families and children are invited to don their costumes for a delightful Halloween celebration at The Heckscher Museum of Art. This event offers a chance to create a spooktacular art activity and take home a festive treat, making for a...

Experience the quintessential New England fall at March Farm! Visitors can pick their own apples and pumpkins, get lost in a sprawling 5-acre corn maze, and enjoy scenic tractor rides. Live music and delicious food trucks add to the festive...

Bring your little goblins and ghouls for a safe and fun trick-or-treating experience at The Shoppes at East Wind. This family-friendly event offers a secure outdoor environment for children to enjoy Halloween festivities. The carousel will also be open, adding...

Get into the Halloween spirit at the Mountain Mist Halloween Harvest! This family-friendly event features a popular Trunk or Treat, a costume contest with exciting prizes, and a chance to meet a friendly llama. Enjoy pumpkin decorating, music, face painting,...

Experience a delightful Fall Festival at the Cold Spring Harbor Fish Hatchery & Aquarium. This family-friendly event offers a variety of activities including fishing, exciting animal encounters, live music, and engaging games. It's a perfect way to celebrate the autumn...

Experience the quintessential fall tradition at Lyman Orchards' Pick Your Own Pumpkin Patch. Nestled on 200 acres overlooking the Connecticut River Valley, they offer a delightful outing for all ages. Select from a wide array of sugar and carving pumpkins,...

Experience the charm of a tenth-generation family farm at Averill Farm's pick-your-own pumpkin patch. Wander through their scenic 30-acre orchard, selecting the perfect apples and pears. Discover a delightful array of local goods, including fresh cider, donuts, jams, pumpkins, gourds,...

Celebrate the harvest season at Lyman Orchards' Corn Maze & Cider Donut Harvest Music Festival. This family-friendly event features a unique "Pizza Pie" themed corn maze filled with facts about Connecticut's pizza culture. Enjoy live music from local bands, explore...

Lace up for the Halloween 5K & Monster Dash! This event features a fast, flat USATF Certified 5K course and a fun Monster Dash for kids 12 and under. Participants can compete for awards in various age groups, and a...

Discover a not-so-scary Halloween celebration at the Westchester Children's Museum. This family-friendly event offers a playful learning environment with interactive exhibits and special programs. Enjoy daily activities and themed weekend events throughout the fall season.

Bring little ghosts and goblins for a spooktacular self-guided Trick or Treat adventure within the historic Main House. Kids can follow a treasure map through each room, collecting treats, prizes, and learning fun facts about the Coe family and their...

Get ready for a spooktacular Halloween at the farm! This family-friendly event features trick-or-treating at numerous stations, unlimited wagon rides, and a fun-filled corn maze. Kids can enjoy crafts and games, while adults can savor treats from local food trucks....

Discover the charm of Wilkens Fruit & Fir Farm's annual fall festival. Wander through their impressive corn maze, a highlight for many visitors. Engage in the classic autumn activity of picking your own apples and pumpkins straight from the source....

Discover the charm of fall at Lenny Bruno Farms Fall Festival. Wander through over 8 acres of pumpkin fields, get lost in a thrilling corn maze, and stock up on seasonal decor like corn stalks and mums. Indulge in fresh...

Immerse yourself in the autumn spirit at the Heritage Farm & Garden Fall Festival. Wander through a captivating corn maze, get creative with pumpkin decorating, and delight in the company of friendly farm animals. Capture memories with abundant photo opportunities...

Join the Ghoul Scout Halloween Happenin' for a night of spooky fun that glows like gold! This family-friendly event features a haunted trail, costume fashion show, pumpkin painting, and exciting games. Enjoy a s'mores bar and Halloween movies as the...

Join Klingberg Family Centers for a fun-filled Trunk or Treat event! This free community gathering offers a safe and exciting way for families to celebrate Halloween. Children can enjoy complimentary face painting, tattoos, and games, with the first 250 kids...

Prepare to be amazed by The Great Jack O'Lantern Blaze, an immersive Halloween spectacle featuring over 7,000 hand-carved, illuminated pumpkins. Wander through themed lands, discover iconic New York landmarks sculpted from gourds, and marvel at a 'wickedly' fun emerald-hued dreamscape....

Get ready to unleash your inner wild side at the Run Wild Halloween Costume Run! This exciting 1.25-mile forest adventure features a thrilling obstacle course with challenges like alligator pools, balance beams, and rope swings. Participants are encouraged to don...

Dive into the heart of Halloween at Sleepy Hollow Country, where the legend of the Headless Horseman comes alive. This region offers a packed schedule of spooky events throughout October, including the dazzling Great Jack O'Lantern Blaze, atmospheric cemetery tours,...