Essex is the sort of town where I can promise my kids we’re “just going for a walk” and somehow end up feeding ducks, looking at scarecrows, eating cookies, and staying out much longer than planned. October takes that energy and turns it all the way up.
I grew up here, and now I get to experience these traditions with my own kids. We do the big outings—cider mills, pumpkin picking, festivals—but some of their favorite afternoons are as simple as the playground behind Town Hall, Toys Ahoy, and one more trip to see the ducks.
Quick family plan: For a regular October afternoon, walk Main Street, find the scarecrows, browse Toys Ahoy and Essex Duck, get a treat, visit the waterfront, and play behind Town Hall. On October 3, build the day around FestiFall. On October 24, head to the Ivoryton Pumpkin Festival in the evening. Verify event updates before leaving home.
FestiFall and Essex scarecrows: Saturday, October 3
This year’s FestiFall runs 1–4 p.m. on Saturday, October 3, 2026, with a “Haunted History” theme. The Essex Board of Trade lists free crafts around town, RiverTales crafts from the Connecticut River Museum, games, a pumpkin scavenger hunt, face painting, caricatures, and a petting zoo. My advice: let the kids lead you from stop to stop instead of trying to tick off every activity.
The scarecrows remain up through October. Online voting opens October 3 and closes October 30. We’ll have one at Grace & Haven—please find it and vote for your favorite (and I won’t be mad if it’s ours). We’re also planning a cider stand at the shop to benefit Soaring Kids Camp for neurodivergent kids through A Brighter Way. Check our events page for the latest shop details.
If you missed FestiFall, a scarecrow walk is still an easy family outing for the rest of the month. Add cookies from Chocolate Geeks, and you’re doing October right.
The Ivoryton Pumpkin Festival: Saturday, October 24
The Ivoryton Village Pumpkin Festival is scheduled for Saturday, October 24, 2026, from 5–7 p.m. in downtown Ivoryton and on the Village Green. It grew from a neighbor’s tradition of lighting a remarkable number of jack-o’-lanterns each Halloween. That neighbor was also my third-grade teacher. Seeing what it has become still makes me smile.
The pumpkins are something to see, and the witches and trunk-or-treat are a huge hit with kids. Grace & Haven had the funniest trunk last year with Cookie Monster, so yes, we’re taking this very seriously. If you’re hungry afterward, Brickside Pizza has a new Ivoryton location. Confirm the festival program and food hours before making a plan.
Halloween in Essex Village
Essex loves a parade, and Halloween on Main Street feels like one big neighborhood party. The parade, costumes, decorations, and trick-or-treating are among the most fun Halloween experiences we’ve had as a family. We’re planning to hand out candy again at Grace & Haven and cannot wait to see what everyone wears.
2026 scheduling note: The exact parade and trick-or-treating details were not confirmed in the sources I checked while drafting. Watch the Essex Board of Trade calendar and our events page for the official time and route before publishing a specific plan. For more of our Halloween history, see our earlier Essex Halloween post.
Our other October traditions
Clyde’s Cider Mill is a classic October outing for us. We’ve also loved pick-your-own days at Lyman Orchards and Bishop’s Orchards. For an outdoors day closer to the river, try Cross Lots, Gillette Castle grounds, Chapman Falls at Devil’s Hopyard, or the Airline Trail; choose a walk that matches your kids’ energy and check trail conditions. We love a beach walk and the Meigs Point Nature Center at Hammonasset, too.
And the food part counts: fried dough at a local fair, cider from the mill, warm chowder, and my mom’s homemade Chex Mix. I would never leave that last one off my personal fall list.
For more outdoor ideas, I collected 20 things worth doing near Essex in fall. If your family loves a drive, use the kid-friendly stops in my foliage route.
The easy Essex afternoon, with or without an event
Here’s what I tell a mom who walks into the shop with kids around five to twelve and asks what to do next: start at the playground behind Town Hall. Head down Main Street to Toys Ahoy and Essex Duck, then to the Connecticut River Museum. Save time for Steamboat Dock and the ducks. Stop for lunch at Olive Oyl’s or pizza at Privateers. Repeat the duck stop if your children are anything like mine.
Please watch the ducks rather than feeding them bread; follow any posted wildlife guidance. My kids call it “feeding the ducks,” but seeing them by the water is the part they really love.
If it rains or turns cold
For an Essex-based day, do the museum, shops, and a long lunch. If everyone needs a bigger indoor adventure, my kids love IT at Jordan’s Furniture in New Haven, which gives us an excuse for Pepe’s Pizza. The Yale Peabody Museum is another favorite, especially for dinosaur lovers; check admission and reservations. We’ve also made a whole day of Supercharged in Montville and enjoyed the free Submarine Force Museum in Groton. The Meigs Point Nature Center has indoor exhibits, but check opening hours before driving to Madison.
Frequently asked questions
What can kids do in Essex, CT, in October?
Walk the scarecrow displays, visit the Connecticut River Museum, browse Toys Ahoy and Essex Duck, play behind Town Hall, and spend time at the waterfront. FestiFall, the Ivoryton Pumpkin Festival, and Halloween add special dates to the month.
When is Essex FestiFall in 2026?
The Essex Board of Trade lists Saturday, October 3, 2026, from 1–4 p.m. Check the official event page for updates and rain plans.
When is the 2026 Ivoryton Pumpkin Festival?
The Ivoryton Village Alliance lists Saturday, October 24, 2026, from 5–7 p.m. Check its event page before traveling.
Come by: Grace & Haven is at 23 Main Street in Essex. Tell us how old your kids are and how much time you have; we’ll help you choose your next stop.
Amy Ihrke is the founder of Grace & Haven, a women’s, baby and kids, and gift boutique on Main Street in Essex, Connecticut. She grew up in Essex, moved away, and came back to experience the town through her children’s eyes. These guides share the places she actually goes, the traditions her family loves, and the local businesses she’s always telling friends and customers about. Find her at Grace & Haven, 23 Main Street.
