11 Fun Fall Activities in Fairfield County, CT [2023]

This crisp cool fall air is making us want to head out with the little ones to do all the fun fall things that the gold coast has to offer. If there are apples on a tree, we are ready to pick. Hayrides? Count us in. Halloween is just around the corner and those apple cider donuts are calling. Here, our guide to some of the best fall activities in Fairfield County.

The Best Fall Activities in Fairfield County

  1. Apple picking

Where: Silverman’s Farm, Easton

When: Apple picking season at Silverman’s runs from late August through early November with a large range of trees at the orchard. Check the website https://www.silvermansfarm.com/pick-your-own-apples/#schedule  for an array of varieties and when to time your trip. Galas are plentiful in early October, sun crisp in mid-October, or wait until November for fujis and pink ladies. Some trees even have low branches, making them easier for smaller pickers.

How: Pre-purchase a bag to fill at the country market (the pies are delish there too) and catch a scenic tractor ride out to the center of the orchard. Make sure to pick only in the designated areas where the fruit is ready.

Bonus: Stay for a browse through Silverman’s Animal Farm, located just across the street. There’s a small admission fee and you can also buy a little bucket of food to help feed the goats, sheep, llamas or buffalo they have on premises. Make a day of it, pack a lunch and have a bite at one of the picnic tables in the park area.

2. Tokeneke Pumpkin Carnival

Where: Tokeneke Elementary School, Darien

When: October 14 from 10 a.m. to 4 p.m.

Price: Free to attend, but ride and game tickets run between $3 and $5.

Fun: The 50-year-running carnival offers food and activities suitable for all ages. Thrill seekers are likely to be into the Cliffhanger, Zero Gravity and Ali Baba rides while younger ones will love the cars, trains and spin rides. Look for lawn games, art activities, face painting and prizes, too. Check out the Nola Physical Therapy + Performance Obstacle Course and stay for performances by School of Rock and Dance on the DL. Grab some food from local Darien favorites like Burgers Shakes & Fries, Crazy Taco Mex, Fjord and Heights Pizza.

3. Hayrides

Where: Sam Bridge Nursery, Greenwich

When: Every Friday and Saturday starting at the end of September, from 2 p.m. to 4 p.m. on Fridays, 10 a.m. to 4 p.m. on Saturdays

Why: Hitch a free hayride to the pumpkin patch where a slew of pumpkins are already cut and lined up, ready to be chosen. Don’t leave without purchasing a take home pumpkin painting or build-a-scarecrow kit.

4. Cider Donuts

Where: Lakeside Diner, Stamford

When: Year round

Yum: There are tons of places to score some pretty darn delicious donuts in our towns, but this cozy breakfast and lunch spot truly has some insane cinnamon-sugar rolled donut goodness, served warm with an outer layer that sits almost like a sweet light crust. Bite in to a soft, cake-like interior that will have you hooked. Sure, they have a full menu of diner faves like pancakes and club sandwiches, but you simply cannot leave without ordering a donut (or 12). Heaven.

5. Fright Night

Where: Ambler Farm, Wilton

When: Last two weekends in October, 6 p.m. to 8 p.m.

Price: $25 per member child; $30 per non-member child

Fun: Date night anyone? Drop the kids (grades 3 to 5) off at the farm for two fun-filled hours of haunted (but not too scary) activities—kids can hitch a ride on a moonlight hayride, add to the guessing jar to win the farm’s largest pumpkin and play various Halloween-themed games. Snacks are included.

6. Stamford Museum and Nature Center Fall Family Fest Sundays

Where: Stamford Museum and Nature Center, Stamford

When: September 24, October 4 & 8; 10 a.m. to 2 p.m.

Price: $10 per member; $20 per nonmember; children 3 and under are free, pre-registration is required.

Fun: The whole family will enjoy a fun-packed morning/afternoon of pumpkin painting, animal visits, games, local food trucks, music, apple cider demos and some time on the sock skating rink. Don’t leave without stopping at the farmer’s market, which is held at the nature center during the event.

Warrup’s Farm in Redding

7. Pumpkin Picking

Where: Warrup’s Farm, Redding

When: Every weekend in October, 10 a.m. to 5 p.m.

How: You can’t pass up this fall activity! Head to this gorgeous family farm to pick your own pumpkins and gourds right off the vine. Or, if you’d rather, head to the farm stand on premises to choose one that’s already been picked. They’re also stocked with apples, cider and maple syrup. Yum. Visit the animals and take the littles through the small meadow maze that’s free and a perfect size to not overwhelm small kids.

8.  Fall Hiking

Where: Weir Pond and Swamp Loop Trail, Wilton

When: Year round

Why: A beautiful two-mile trail that’s easy enough for small children (or beginner adults). Take in the gorgeous fall foliage as you walk through the mostly flat trail (with a few small rocky areas and water crossings). Known as “easy” as far as hikes go, you’ll love catching sights of beautiful birds as you work your way around the large pond. Dogs are allowed if they’re leashed.

9. Halloween Block Party

Where: Elm Street, New Canaan

When: Sunday, October 29

Why: New Canaan’s favorite Halloween celebration! The main drag will be closed to vehicular traffic so wear your costume and trick-or-treat from store-to-store along Elm. Get there a little early to score a gift bag sponsored by Walter Stewart’s for the first 500 children. Stay for performances by School of Rock and parade through town to show off your stellar costumes.

10. Not-so-Scary Scavenger Hunt

Where: The SoNo Collection, South Norwalk

When: Last three weekends in October, 12 p.m. to 4 p.m.

Price: $15 per child to benefit The Norwalk Conservatory

Why: A Halloween-themed indoor hunt for kids 10 and under is sure to put everyone into the spirit without all the scariness attached. Kids will stroll through the Not So Scary Halloween Scavenger Hunt, spot some witches and goblins, take part in some games and challenging tasks and indulge in (nut free) sweet treats. The whole hunt should take about 20 to 25 minutes to complete.

11. Pink or Treat Parade

Where: The Westport Library

When: Sunday, October 22

Price: Free

Why: This Halloween celebration will be lead by Pinkalicious author Victoria Kann!  What better way to start your spooky holiday than with a Pinkalicious-themed Halloween Parade! Kann will read from her book Pink or Treat, and kids can take part in giveaways and a Halloween parade. Costumes encouraged!

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