There’s something special about this holiday here. Historic neighborhoods come alive with trick-or-treaters, downtown streets fill with costumes, and local restaurants join in with themed menus and parties.
Whether you’re planning an afternoon with the kids, craving a good scare, or gathering friends for a night out, there’s no shortage of options. Here’s your guide to events in Fairfield, Westport, Norwalk, Stamford, Greenwich, Weston and beyond, October 28–November 1.
Family-Friendly Halloween Events in Fairfield County
The MOMbies Take Over Fairfield
Saturday, October 31 | 5:30, 6:30 & 7:30 PM | Fairfield Town Hall Green
What began in 2016 as a secret Halloween flash mob of moms has become one of Fairfield’s most recognizable traditions. Moms, grandmothers, friends and neighbors step into zombie makeup and perform signature dances on the Town Hall Green, raising money for metastatic breast cancer research at Memorial Sloan Kettering Cancer Center. They call it “dance to donate”®, and the result is a little Halloween madness with extraordinary impact.
Westport’s Children’s Halloween Parade
Wednesday, October 28 | 3:30 PM | Downtown Westport
Costumed children trick-or-treat along Main Street, then head toward Town Hall and Veterans Green for a community celebration. Local businesses join in, and there’s plenty of room to show off creative costumes.
Kids’ Fall-O-Ween at 314 Beer Garden
Thursday, October 29 | 4–7 PM | Norwalk
314 Beer Garden gets a spooky makeover, and the little ones are invited. Expect costumes, games and activities, plus wood-fired pizza in a relaxed outdoor setting.
Explore events at 314 Beer Garden
Fairfield Public Library’s Halloween Parade
Friday, October 30 | 10 AM | Main Library, Fairfield
Children are invited to dress in costume for a festive parade around and through the Main Library, collecting treats along the way. Bring a bag for the goodies! The event is for ages five and under, and registration is required.
Halloween Spooktacular at New Canaan Nature Center
Friday, October 30 | 5:30–7:30 PM | New Canaan
Meet some fiendish friends, including spiders, snakes and owls, then make creepy crafts and roast marshmallows around a crackling campfire while swapping spooky stories. The evening ends with the nature center’s one-of-a-kind jack-o’-lantern walk. Costumes are welcome, and it’s held rain or shine.
Register for the Halloween Spooktacular
Greenwich Greet & Treat
Saturday, October 31 | 11 AM–2 PM | Greenwich Avenue
Greenwich Avenue and the surrounding business district come alive with trick-or-treating at favorite local stores, family activities and a fun-filled Kid Zone. Presented by Greenwich Moms, the event brings families together while supporting downtown businesses.
Greenwich Greet & Treat details
Halloween Party, Trunk & Treat & Candy Trail
Saturday, October 31 | 3–5 PM | Mill River Park, Stamford
Decorated trunks, a trick-or-treat trail and a carousel party finale make this free, family-friendly afternoon at Mill River Park a treat for all ages. Follow the trail through the park collecting candy, then celebrate at the Nissen Carousel with rides, music, games, crafts and photos with costumed characters.
Register for the Mill River Park party
Haunted Attractions & Halloween Nights Out
Harvest Fair After Dark
Friday & Saturday, October 30–31 | 7–10 PM | Fairfield
Want something beyond the usual costume party? This Fairfield property turns into a nighttime adventure of haunted hayrides and wooded trails. Between scares, gather around the firepits and warm up with seasonal refreshments.
Explore Harvest Fair After Dark
Legends of Fear
October 29–30 & November 1 | Starting at 7 PM | Shelton
For those who like their Halloween with a little more adrenaline, Legends of Fear at Fairview Tree Farm offers a haunted hayride and immersive haunted attractions designed to keep you on edge. It’s a favorite seasonal destination for thrill-seekers and an ideal outing for older teens and adults.
Three Days of the Dead at Geronimo
October 30–November 1 | Various Times | Fairfield
Geronimo Tequila Bar & Southwest Grill stretches the holiday into a three-day celebration inspired by Día de los Muertos. Expect live music, DJs, food and drink specials, brunches and a costume contest, from Friday’s flamenco guitar to Sunday’s mariachi. It’s a festive way to celebrate Halloween weekend with friends right in the heart of downtown Fairfield.
Adults-Only Halloween Nights at Lachat Town Farm
Friday & Saturday, October 30–31 | 7 PM | Weston
Two adults-only nights of fright and delight begin around the firepit with hot toddies, wine, beer and Halloween chocolates. At 7:30 PM, head to the candlelit barn for dramatic readings of Edgar Allan Poe’s The Tell-Tale Heart and The Masque of the Red Death.
Celebrate the Season, Fairfield County Style
Beyond the costumes and haunted trails, Halloween shows what makes Fairfield County such a special place to call home. Fairfield’s community traditions, Westport’s walkable downtown, Greenwich Avenue’s holiday spirit and Norwalk’s lively restaurant scene each bring their own personality to the season.
At The Agency Fairfield County, we’re proud to be part of the communities that make this area so vibrant. Whether you’re new to the neighborhood or have called it home for years, we hope you find some Halloween magic close to home.
Thinking about making a move? Start your home search or contact our team.
Happy Halloween from all of us at The Agency Fairfield County!
Event details are subject to change. Check with individual organizers for current schedules, tickets and availability.
