Things to do in Fairfield County this week and next feel especially inviting as October settles in and Halloween gets closer. This is the stretch of fall when familiar places take on a different energy, with costumes appearing, pumpkins everywhere and neighbors making plans to meet up. Some outings are made for children, while others give adults a good reason to try something new or spend an evening out. Even a simple weeknight plan can feel like a welcome break from the usual routine. The best part is how much is happening close to home, right in the places we pass every day. Pick what fits your mood and enjoy this part of the season.
Across Fairfield County
1. 56th Annual Old Greenwich School Pumpkin Patch
Saturday, October 17, 2026
Old Greenwich School, Old Greenwich
The annual fall celebration brings live entertainment, a Grit Ninja hay maze obstacle course, a petting zoo and inflatables to the school grounds. Food trucks, games, seasonal activities and raffle prizes round out the afternoon.
2. Silent Disco at the Carousel
Friday, October 23, 2026
Nissen Carousel at Mill River Park, Stamford
Guests can borrow headphones, choose between two DJs and dance beneath the evening sky. The free, all ages event also includes lawn games, refreshments for purchase and carousel rides.
3. Fall Harvest Festival
Saturday, October 10, 2026
Highland Farm, Darien
Darien welcomes the season with live music, family activities and local vendors at Highland Farm. The free, all ages gathering offers an easy way to spend a fall afternoon together.
4. Pumpkin Fest 2026
Saturday, October 17, 2026
Wilton Historical Society, Wilton
Open hearth cooking, blacksmithing, lawn games and a pumpkin scavenger hunt bring fall traditions to the museum campus. Families can also meet baby goats, decorate a pumpkin and enjoy cider and donuts.
5. 2026 Halloween on the Green
Sunday, October 25, 2026
Fairfield Museum Commons, Fairfield
Fairfield marks Halloween with trick or treating, giveaways, food vendors and activities around the historic buildings. A bounce house and family friendly displays add more ways to spend the afternoon on the museum grounds.
Greenwich Magazine
1. 56th Annual Old Greenwich School Pumpkin Patch
Saturday, October 17, 2026
Old Greenwich School, Old Greenwich
The annual fall celebration brings live entertainment, a Grit Ninja hay maze obstacle course, a petting zoo and inflatables to the school grounds. Food trucks, games, seasonal activities and raffle prizes round out the afternoon.
2. Social Studio Paint Night
Wednesday, October 21 and Thursday, October 22, 2026
YWCA Greenwich, Greenwich
A relaxed, guided painting experience leads participants step by step through creating an original work to take home. The Wednesday session is for teens ages 13 to 18, and the Thursday session is for adults.
3. Halloween Happenings
Friday, October 23, 2026
Bendheim Western Greenwich Civic Center, Greenwich
Families can dance in Dracula’s Den, play games and collect candy and prizes during this town Halloween celebration. Costumes are encouraged, with a family costume contest and treat bags for children.
4. Birding at the Bruce Museum with Greenwich Audubon
Saturday, October 24, 2026
Bruce Museum, Greenwich
A Greenwich Audubon guide leads a walk from the museum to the neighboring Oneida Sanctuary. Participants can look for waterfowl, shorebirds, herons and egrets while learning about the coastal salt marsh habitat.
5. Howl & Prowl
Sunday, October 25, 2026
Greenwich Town Hall, Greenwich
Dogs and their people can gather for an afternoon Halloween costume party at Town Hall. The community event offers a playful way for local pet lovers to celebrate the season while supporting Adopt A Dog.
Stamford Magazine
1. Sound Steps 5K Walk/Run for Mental Health Recovery
Saturday, October 17, 2026
Cove Island Park, Stamford
Runners and walkers follow a waterfront course while raising awareness and funds for mental health recovery. Proceeds support Laurel House programs that help local individuals pursue education, employment and independent living.
2. Snow White and the Seven Dwarfs
Saturday, October 17, 2026
The Palace Theatre, Stamford
The United European Ballet brings the familiar fairy tale to the stage through classical dance, colorful characters and theatrical scenery. The performance was created for audiences of all ages.
3. Planets & Pumpkins Fall Fest Sundays
Sunday, October 18 and Sunday, October 25, 2026
Stamford Museum and Nature Center, Stamford
Fall traditions meet space themed activities at this annual family festival. Pumpkin decorating, an inflatable corn maze, live animals, planetarium experiences and apple slingshots are among the activities planned throughout the grounds.
4. Silent Disco at the Carousel
Friday, October 23, 2026
Nissen Carousel at Mill River Park, Stamford
Guests can borrow headphones, choose between two DJs and dance beneath the evening sky. The free, all ages event also includes lawn games, refreshments for purchase and carousel rides.
5. Stories, Rhythms & Flavors, a Hispanic Heritage Month Program
Saturday, October 24, 2026
Ferguson Library South End Branch, Stamford
This all ages celebration brings live music, storytelling, food and a craft activity together in one afternoon. The program highlights the cultures, traditions and stories of the local Hispanic community.
New Canaan, Darien and Rowayton Magazine
1. CT Stage Co Presents My Fair Lady
Saturday, October 17 and Sunday, October 18, 2026
New Canaan Library, New Canaan
Connecticut Stage Company presents the story of Eliza Doolittle and her unexpected journey into London high society. The production features familiar songs including The Rain in Spain and I Could Have Danced All Night.
2. Autumn Tavern Night, Bonfire, Beer and Bites
Saturday, October 17, 2026
Museum of Darien, Darien
The museum hosts an autumn evening with a bonfire, beer and light bites on its historic property. Guests can gather outdoors while enjoying a relaxed night with friends and neighbors.
3. Halloween Story, Craft, and Art Exploration at the Carriage Barn
Sunday, October 18, 2026
Carriage Barn Arts Center, New Canaan
Families can hear a Halloween story, make a seasonal craft and explore the Annual Member Show together. The casual format makes this an easy creative outing for a fall afternoon.
4. Fall Harvest Festival
Saturday, October 24, 2026
The Mather Homestead, Darien
Pony rides, hayrides, face painting, crafts and live music fill the historic property during this annual family event. Pumpkins and seasonal treats complete the afternoon.
5. Halloween Nightfair Returns to SoNo
Saturday, October 24, 2026
Washington Street, Norwalk
Washington Street closes to traffic for an all ages street festival with music, carnival rides, games and a costume contest. Food trucks, local vendors, pumpkin painting and trick or treating continue throughout the afternoon and evening.
Westport, Weston and Wilton Magazine
1. Pumpkin Fest 2026
Saturday, October 17, 2026
Wilton Historical Society, Wilton
Open hearth cooking, blacksmithing, lawn games and a pumpkin scavenger hunt bring fall traditions to the museum campus. Families can also meet baby goats, decorate a pumpkin and enjoy cider and donuts.
2. Who Was Alice DeLamar?
Sunday, October 18, 2026
Weston Public Library, Weston
Author Nona Footz discusses her new biography of heiress and arts patron Alice DeLamar. The talk looks at the complicated woman behind one of the most notable historic estates in Weston.
3. Intuitive Abstract Expressionism: an immersive art experience with Melissa Benedek
Sunday, October 25, 2026
MoCA CT, Westport
Artist Melissa Benedek leads an immersive painting workshop using color, movement, texture and music. No experience is necessary, and all materials are included for the adult class.
4. 2026 Halloween on the Green
Sunday, October 25, 2026
Fairfield Museum Commons, Fairfield
Fairfield marks Halloween with trick or treating, giveaways, food vendors and activities around the historic buildings. A bounce house and family friendly displays add more ways to spend the afternoon on the museum grounds.
5. Full Moon & Bat Hike
Monday, October 26, 2026
Earthplace, Westport
An Earthplace naturalist leads an evening walk in search of bats and other nocturnal wildlife. Families can listen for activity along the trails, look for constellations and experience the sanctuary after dark.