Christmas with Grandkids in CT and Westchester (2026)

The Christmas memories grandkids keep are rarely about what was under the tree. They’re about the cold walk through the tree farm, the lights seen from the back seat, and the cookies that came out lopsided. This guide covers the local outings in Fairfield County and Westchester that fit a grandparent’s December, plus the traditions worth starting this year.

At a Glance

• Christmas 2026 is Friday, December 25. Christmas Eve is Thursday, December 24.
• Best early-season outing: GLOW Wild at Connecticut’s Beardsley Zoo in Bridgeport, Thursday to Sunday evenings through December 20.
• Best outing for grandparents who feel the cold: Westchester’s drive-thru holiday light show at Kensico Dam Plaza in Valhalla. Everyone stays in the warm car.
• Best tradition: cutting your own tree at Jones Family Farms in Shelton. Reservations are required on the first weekend in December.
• Best for the week after Christmas: Stepping Stones Museum for Children and the Maritime Aquarium, both in Norwalk.

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Local Christmas Outings

Cut Your Own Tree at Jones Family Farms, Shelton

Jones Family Farms is one of Fairfield County’s best-known cut-your-own Christmas tree farms, and walking the rows with a grandkid who gets to choose is a tradition in itself.

What grandparents should know:

• Reservations are required on the three days of Thanksgiving weekend and on the first weekend in December, and encouraged on every other weekend.
• Handsaws and twine are available at the farm.
• The property is large. The farm suggests bringing a stroller or wagon for little ones, plus sturdy, waterproof footwear.
• Accessible parking is in the Barnyard Village lot. The terrain is unpaved and uneven; the farm says most wheelchairs manage it in good weather.
• Measure your ceiling before you go. A tree always looks smaller in the field.

Check the farm’s site for this year’s opening date, hours and tree prices before you drive.

GLOW Wild at Connecticut’s Beardsley Zoo, Bridgeport

Hundreds of handcrafted illuminated lanterns and more than 40 displays light up Connecticut’s Beardsley Zoo on evenings from October 1 through December 20, 2026, Thursday to Sunday, 5:30 to 9:30 pm.

• Tickets are sold online. Buy ahead, especially for weekends in December.
• The carousel runs during GLOW Wild, which is a good reward at the end of the walk.
• Wheelchairs and scooters are available, which helps a grandparent who would rather not walk the whole loop.
• It ends December 20, so plan it for early December rather than Christmas week.

Details at beardsleyzoo.org.

Drive-Thru Holiday Lights at Kensico Dam Plaza, Valhalla

Every November and December, Westchester County Parks and the Westchester Parks Foundation turn Kensico Dam Plaza into Westchester’s Winter Wonderland, a drive-thru holiday light show. For grandparents it may be the easiest outing of the season: no walking, no cold, and a toddler can fall asleep halfway through without ruining anything.

This year’s dates, hours and per-car prices are posted each fall at wwinterwonderland.com. Check before you go, and pick a weeknight for a shorter line.

Dickens’s Christmas Carol, Sleepy Hollow

Historic Hudson Valley presents Dickens’s Christmas Carol, told live by storyteller Jonathan Kruk, on December weekends at the Old Dutch Church in Sleepy Hollow. Best for grandkids who can sit through a longer story. Check this year’s dates and tickets at hudsonvalley.org.

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The Week After Christmas

School is out, the new toys have lost a little shine, and everyone needs to get out of the house. Three indoor picks:

Stepping Stones Museum for Children, Norwalk

Hands-on from wall to wall, for toddlers through about age 10. Stepping Stones is open 10 am to 5 pm and closed every Wednesday, so plan around the midweek gap. Admission is $20 for adults and children and $16 for seniors over 62, sold only at the Welcome Desk (not online). Arrive at opening on a holiday-week day.

The Maritime Aquarium, Norwalk

Seals, sharks and a touch tank. The Maritime Aquarium is open daily 10 am to 5 pm, closes at 3 pm on Christmas Eve and is closed on Christmas Day. Tickets and prices are on the aquarium’s site.

Hudson River Museum, Yonkers

The Westchester pick. The Hudson River Museum pairs art and history galleries with a planetarium. It is open Wednesday to Friday noon to 5 pm and weekends 11 am to 5 pm, and closed on Christmas Day and New Year’s Day.

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The One Question That Always Works

“What’s one thing from this year you want to remember forever?”

Ask it on Christmas Eve. Write each answer on a card with the date and the child’s age. Keep the cards in the ornament box, so they come out every December with the decorations.

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Free Traditions (No Budget Required)

The First Ornament

The first ornament out of the box is always theirs to hang. It costs nothing, and by the third year they will remind you before you open the box.

The Christmas Morning Call

If you won’t be together on Christmas morning, call before the presents. Not to talk about presents: tell them one specific thing you noticed about them this year. Keep it under two minutes.

The Neighborhood Lights Walk

After dinner one night in December, bundle up and walk the block with a flashlight. Everyone votes for the best-decorated house. Same walk, same vote, every year.

One Story After the Presents

Once the wrapping paper is cleared, read one story aloud. Same book every year works best. See The Night Before Christmas below.

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Things to Do Together (and Bring Along)

Looking for gifts by age instead? See our 2026 holiday gift guide for grandkids. The picks below are for doing Christmas together.

Wilton Mini Village Gingerbread Kit

~$25–30. A village of small gingerbread buildings goes up faster than one big house, so several grandkids can decorate at once and nobody fights over the roof. Ages 5 and up. Put down newspaper first. Shop on Amazon →

Christmas Cookie Cutters (Stainless Steel, 9 Shapes)

~$12–15. The same cookie recipe, the same bowl, the same cutters every Christmas Eve. Tree, star, snowman, bell and gingerbread-man shapes, 2 to 3.5 inches. Shop on Amazon →

Skillmatics Foil Fun Christmas Ornaments

~$18–22. A no-mess foil-art ornament craft for ages 4 to 9. Date the back of each one, and in ten years the tree tells the story of who made what. Shop on Amazon →

The Night Before Christmas (Classic Edition)

~$8–12. The one story to read after the presents, every year. The classic illustrated edition, in a sturdy hardcover. Shop on Amazon →

HotHands Hand Warmers (10 Pairs)

~$7–12. For the tree farm and the lantern walk. Tuck one in each small mitten and one in your own pocket, and the outing lasts an extra half hour. Shop on Amazon →

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FAQ

Where can grandparents cut their own Christmas tree near Fairfield County?

Jones Family Farms in Shelton is a well-known cut-your-own farm in the county. Reservations are required on Thanksgiving weekend and the first weekend in December, and handsaws and twine are available at the farm. Check its site for this year’s opening date and prices.

When is GLOW Wild at Beardsley Zoo in 2026?

GLOW Wild runs Thursday to Sunday, 5:30 to 9:30 pm, from October 1 through December 20, 2026, at Connecticut’s Beardsley Zoo in Bridgeport. Tickets are sold online, and wheelchairs and scooters are available.

What is a good Christmas lights outing for grandparents who don’t want to walk far?

The drive-thru holiday light show at Kensico Dam Plaza in Valhalla, run each November and December with Westchester County Parks. You stay in the car for the whole show. This year’s dates and prices are posted at wwinterwonderland.com.

What is open the week after Christmas for grandkids in Norwalk and Yonkers?

Stepping Stones Museum for Children (closed Wednesdays) and the Maritime Aquarium in Norwalk are both open 10 am to 5 pm. The Hudson River Museum in Yonkers is open Wednesday to Sunday but closed on Christmas Day and New Year’s Day.

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Make It a Tradition

Pick one thing: the tree farm, the lights drive, the cookie cutters or the story after the presents. Do it every December. Traditions don’t feel like traditions the first time. By the third year, grandkids will be asking when you’re going to do the thing. By the tenth, they’ll do it with their own kids.

Planning more of the season? See our Thanksgiving guide for grandparents or browse indoor activities in Fairfield County, CT and Westchester County, NY.