Pick Your Own Apples and Pumpkins and Pack the Perfect Picnic

Fall means "pick your own" in New England - combine your day trip with a picnic for a farm-tastic day!

After a long, warm summer, the night air is slowly beginning to turn crisp and the leaves are starting to show signs of yellow and orange (and soon red), autumn has arrived in New England. And in Connecticut, with over 60 varieties of apples grown on beautiful, sprawling farms, and pumpkins ready to harvest, autumn means apple and pumpkin picking. Let's face it, there really is nothing better than a juicy, freshly picked apple and the perfect Halloween pumpkin.

Feel like day-tripping for pumpkins and apples? We made a list of some of the popular farms a short(ish) drive from Ridgefield that offer pick your own apples, and in some cases, pumpkins too!

Pack the perfect picnic for picking (say that 5 times in a row!)

After you pack the kids (and maybe the family dog) into your car, we suggest you make a pit-stop at 109 Cheese and Wine. With locations in Kent and Ridgefield, 109 is at the center of this fun, family, fall activity.

We spoke with Todd Brown, and he’s waiting for you with the perfect picking provisions! The 109 team will pack a picnic lunch that will pair perfectly with the apples you’ll likely be munching on! Some 109 fall favorites: 

  • Cheese and wine (of course). 

  • Rose, a pick-your-own favorite among the 109 family

  • Freshly made Baguette sandwiches (artisan bread, fresh meat, the best cheese)

  • Charcuterie 

  • Smoked salmon

  • And MORE, stop in or call for additional picnic provisions!

Bring your own picnic basket encouraged (109 offers some beauties if you want to purchase one!) For your pick-your-

 OK, now you’re ready to head to the farm!

Jones Family Farms is located at 606 Walnut Tree Hill Road, Shelton, CT. 

Pumpkin picking only. Open Sept 18 and 19, 12 to 5:30 pm, for “Preview Weekend”, then we open daily starting on Sept 25.

Notes front the farm: “We have a GREAT CROP OF PUMPKINS this year, and we look forward to sharing it with you!”

For additional information, visit Jones Family Farm online or call (203) 929-8425.

Silverman’s Farm, located at 451 Sport Hill Farm in Easton, CT. Open 7 days a week.

Apple picking only. Click here for schedule.

Beardsley’s Cider Mill and Orchard located at 278 Leavenworth Road in Shelton, CT

Apple picking only. Saturday & Sunday, September 11th & 12th we picking Honeycrisp (they’re usually all picked within 3 hours!), Gala and McIntosh

Warrup's Farm is located at 51 John Read Road, West Redding, CT.

Pumpkin picking. Open weekends in October from 10am to 5pm.

Warrup’s Farm is a small farm using organic methods, operated by the Hill family During October weekends & Columbus Day Monday, pick pumpkins off the vine.

Greig Farm is located at 227 Pitcher Ln, Red Hook, NY.

Pick your own apples and pumpkins.

Enjoy 400 acres of rustic charm, make friends with the goats, and shop the farmers market seven days a week. Greig Farm 9 am to 7 pm for picking apples and pumpkins.

Visit Greig Farm online here

Blue Jay Orchards is located at 125 Plum Tree Road in Bethel.

Apple picking only. Pumpkin “patch”

While the farm has a large pumpkin patch, they don't offer "pick your own". The farm does offer pick your own apples.

Visit them online here for call (203) 748-0119

Ellsworth Farm is located at 461 Cornwall Bridge Road (Route 4) in Sharon, CT.

Apple and pumpkin picking, plus peaches and Asian pears.

Download our 2021 Pick Your Own brochure

Pick-Your-Own at Ellsworth Farm is open early September to late October on Fridays, Saturdays, and Sundays at both the Home Farm and Sunnymount locations from 10:00-5:00, weather permitting.

Rogers Orchards is located at 336 Long Bottom Road in Southington, CT

Pick your own apples only.

Read more about Pick-Your-Own farms in Connecticut here!

No. 109 Cheese and Wine Market, The Marketplace at Copps Hill, 109 Danbury Road, Ridgefield. T. 203-438-5757.


Tue–Thu: 10am to 6pm

Fri & Sat: 9am to 6pm

Sun: 10am to 4pm

109 Cheese Market Kent, 7 Old Barn Road, Kent, CT,.860.592.0366.


Wednesday through Saturday from 10 am to 5pm.

Visit 109 Cheese and Wine online here.