Farms & Pick-Your-Ownin Fairfield County, CT
Seasonal outdoor adventures. 63 venues listed.
Grandparent tip: Wear clothes you don't mind getting dirty. Many farms are seasonal — always call ahead before making the trip.
Read: 5 Free (or Nearly Free) Days Out →- 🔍 Farm Scavenger Hunt — Find a tractor, a barn cat, the biggest vegetable on the property, a piece of equipment you can't name, and something that smells.
- 🏆 Pick a Winner — Everyone picks the best-looking apple, berry, or pumpkin — the farmer (or the grandkid) is the final judge.
- 🧮 Farm Math — If strawberries cost $4/lb, how many can we pick for $10? Real-world math that actually lands with kids.
- • Weekday farm visits skip the weekend "agri-tourism" event surcharges that can double the admission price.
- • Buying direct from the farm stand usually gets you twice the produce for the same price as a grocery store — and you picked it yourself.
Blue Jay Orchards
122-acre orchard with 20+ apple varieties & hayrides
Jones Family Farms
Strawberries, blueberries, pumpkins & hayrides since 1848
Silverman's Farm
Pick-your-own apples, cider donuts & a 5-acre animal farm
Make it a memory, not just a trip
Farms teach grandkids where things come from — and grandparents what they've forgotten.
Ask this today
"If you could grow anything in the whole world on your own farm, what would you grow first?"
🆓 Free memory-making ideas
- 🍎
Fill a Bag Together
For pick-your-own farms: grandkids pick, grandparents carry. Make it a counting game — who picks the most perfect apple/berry/pumpkin in the next five minutes? The crookedy one always wins.
- 📸
Before and After
Take a 'before' photo of the empty bag at the start and an 'after' photo when it's full. Add both to a photo album labeled by farm and date. Watch how the arms change over years.
- 🌾
What Was Here Before?
Ask grandkids what they think this land was before it was a farm. Before that? Before that? Take turns going further back. This one sparks surprisingly long conversations.
🎨 Arts & crafts to do together
- 🖨️
Veggie Stamp Prints
Cut an apple, pepper, or potato in half. Dip in paint and stamp on paper. Makes surprisingly beautiful patterns. Do it that same afternoon while the farm visit is still fresh.
Supplies: Paint, paper, produce from the farm — $1–3.
Shop: Crayola Watercolor Paint Set ($4–6) → - 🥧
Make Something With It
Whatever you picked today, make something together within 48 hours: apple sauce, berry jam, pumpkin soup. The recipe doesn't need to be great. The cooking together is the point.
Supplies: Whatever you picked — already have it.
🎒 BYOF — Bring Your Own Fun
Crayola Watercolor Paint Set
For veggie stamping that afternoon, or painting the farm from memory when you get home.
Ruled Index Cards (500 count)
Write the recipe on an index card together on the farm — whatever you're going to make when you get home. Keep the card.
Bicycle Standard Playing Cards (2-Pack)
For the wait at the farm stand or the car ride home.
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Also in Westchester County, NY
Browse farms & pick-your-own venues across Westchester — Yonkers, White Plains, New Rochelle, and more.
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