5 Free (or Nearly Free) Days Out with Grandkids in Fairfield County — Grandkids Guide

The most memorable grandkid days are rarely the expensive ones. Theme parks and big outings have their place, but what grandkids actually remember — and ask to do again — are the simple things done consistently and well.

Here are five low-cost days that hold up.

Day 1: The Beach + Ice Cream Combo

Cost: $10–$20 total (state park parking fee + one ice cream each)

Morning: Sherwood Island State Park, Westport — arrive by 9am, bring a blanket, let them do whatever they want in the sand. No agenda, no schedule. Two hours of this is enough.

Midday: Pack sandwiches and eat at the picnic pavilions. This is part of the day, not a break from it. Eating outside is its own kind of fun for young kids.

On the way home: One stop at any local ice cream shop. The ice cream costs more than the beach parking. That’s fine.

Why it works: The day has a natural arc — active, then calm — and the ice cream punctuates it perfectly. Kids know it’s coming and it becomes something they look forward to.

Day 2: The Farm Morning

Cost: Free to $10 (some farms have small admission fees for activities)

Fairfield County has working farms that welcome visitors, especially in spring and fall. A farm morning — walking the grounds, maybe picking something, seeing the animals — is deeply satisfying for young grandkids in a way that’s hard to explain but easy to observe.

What to look for: Farms with animals you can get close to, or pick-your-own activities (strawberries in June, apples in September). Walking paths that aren’t too muddy. A clean restroom.

Grandparent tip: Dress everyone in clothes they can get dirty. This is the whole point.

Day 3: The Library Saturday

Cost: Free

This one sounds like a consolation prize. It isn’t.

Public libraries in Fairfield County run genuinely good programs for young kids — story times, craft hours, STEM activities — most of them free and drop-in. Even outside of structured programs, a couple of hours at the children’s section with a grandkid is time well spent. You read to them. They pick books they’d never pick at home. You check out a pile and take them home.

The underrated part: Libraries are quiet, climate-controlled, and have seating. As a grandparent activity, it’s about as low-stress as it gets.

Make it a ritual: The same library, every few months, checking out books together. The librarians will start to know you. That’s worth something.

Day 4: The Long Picnic

Cost: Whatever groceries you buy (usually under $15)

Pick a park with a good view — a Sound-facing bench, a spot by a river, a picnic table with some shade. Pack more food than you think you need. Bring a frisbee or a ball.

That’s it. That’s the day.

The secret of the long picnic is that nothing is scheduled, so nothing can go wrong. You eat when you’re hungry, you throw the ball when you feel like it, you sit and talk when the kids are tired. There’s no admission fee, no parking permit, no online booking.

Grandkids who grow up having long picnics with their grandparents carry that forward. It becomes part of what they think a good day looks like.

Day 5: The Ice Cream Tasting Tour

Cost: $15–$25 (a few scoops at two or three shops)

This one is a grandparent classic for a reason. Pick two or three ice cream shops within a reasonable drive and do a tasting tour. One scoop each, compare notes, decide which is best.

The activity is the conversation: Which flavor? Which place was better? What would you get next time? A six-year-old who has just tried three different chocolate ice creams and has very specific opinions about them is one of the great joys of grandparenting.

Fairfield County has good ice cream. Farm-fresh spots, classic soft-serve stands, old-school parlors. This works as a spring kickoff, a summer regular, or an October tradition with apple cider doughnuts mixed in.

The Bigger Point

The days that end up mattering most are usually the ones that cost the least. Not because money doesn’t matter, but because experiences without a price tag tend to be the ones with the least friction, the least expectation, and the most room for the actual moment to happen.

Pick one of these. Put it on the calendar. See what happens.

Find specific spots for each of these days in Fairfield County →