The Best Places for Apple & Pumpkin Picking Near Greenwich, CT

There’s something distinctly New England about a fall afternoon spent wandering through an orchard, picking apples, searching for the perfect pumpkin and ending the day with a fresh cider donut.

While Greenwich itself doesn’t have large pick-your-own orchards, some of the area’s best fall destinations are within an easy drive. Whether you’re looking for a quick afternoon outing or a full day in the countryside, these are some of the best places for apple and pumpkin picking near Greenwich this fall.

1. Blue Jay Orchards | Bethel, CT

For a classic Fairfield County fall experience, Blue Jay Orchards is an easy place to start.

The 122-acre orchard features more than 8,000 producing apple trees and more than 20 varieties throughout the season. Visitors can pick their own apples before heading to the farm market and bakery for cider, pies and the farm’s popular cider donuts.

The fall experience extends beyond the orchard, with a pumpkin patch featuring pumpkins, miniature pumpkins and gourds in a variety of shapes and sizes.

Address: 125 Plumtrees Road, Bethel, CT

2. Silverman’s Farm | Easton, CT

A longtime Fairfield County favorite, Silverman’s Farm offers plenty to do beyond apple and pumpkin picking.

The Easton farm features pick-your-own apples, pumpkins and seasonal decorations, along with a country market and animal farm. Visitors can make an afternoon of exploring the property, picking seasonal produce and stopping by the market for fall favorites.

For families or anyone looking for a little more than a traditional orchard visit, Silverman’s offers a well-rounded fall outing.

Address: 451 Sport Hill Road, Easton, CT

3. Beardsley’s Cider Mill & Orchard | Shelton, CT

A visit to Beardsley’s is as much about the cider and cider donuts as it is the apples.

The Shelton orchard offers pick-your-own apples along with fresh-pressed cider, cider donuts, pies and other seasonal treats. After spending time in the orchard, visitors can stop by the cider mill and bakery to bring a little bit of fall home with them.

It’s a classic Connecticut autumn experience and a great option for a leisurely weekend afternoon.

Address: 278 Leavenworth Road, Shelton, CT

4. Outhouse Orchards | North Salem, NY

Just across the Connecticut border, Outhouse Orchards offers a picturesque setting for a fall day in the country.

The North Salem farm is a convenient option for Greenwich residents looking to head north for apple and pumpkin picking while enjoying the scenic roads and countryside along the way.

Make a day of the trip by pairing a visit to the orchard with lunch or a stop at another local farm stand.

5. Bishop’s Orchards | Guilford, CT

Located along the Connecticut shoreline, Bishop’s Orchards is worth the slightly longer drive for a full fall outing.

The farm offers pick-your-own apples and pumpkins, with more than 20 apple varieties grown throughout the orchard. The season gives visitors the chance to experience different varieties as they ripen throughout the fall.

Beyond picking, the farm market offers seasonal products and plenty of reasons to linger after leaving the orchard.

Address: 1355 Boston Post Road, Guilford, CT

6. Castle Hill Farm | Newtown, CT

For those more interested in pumpkins than apples, Castle Hill Farm is a festive fall destination.

The Newtown farm’s pumpkin patch is complemented by a corn maze, hayrides and other seasonal activities, making it easy to turn pumpkin picking into an entire afternoon.

It’s particularly well suited for families looking to add a few classic fall activities to their day.

Address: 1 Sugar Lane, Newtown, CT

7. Lyman Orchards | Middlefield, CT

If you’re willing to make a longer day trip, Lyman Orchards offers one of Connecticut’s more expansive fall experiences.

The farm’s Pick-Your-Own operation includes apples and pumpkins, while additional seasonal attractions include a corn maze and farm market. With a large selection of apple varieties and plenty of activities, there’s enough to fill an entire autumn day.

Before visiting, check the farm’s website for current picking conditions, available varieties and hours.

Address: 105 South Street, Middlefield, CT

8. March Farm | Bethlehem, CT

For a full day in the countryside, head to March Farm in Bethlehem.

The farm offers apple picking in the fall along with pumpkins, seasonal produce, a farm market, animals and other activities. It’s farther from Greenwich than the other options on this list, but makes a nice destination for a weekend day trip.

Address: 160 Munger Lane, Bethlehem, CT

Tips for Planning Your Fall Outing

Check before you go. Apple varieties, pumpkin availability, hours and picking conditions can change throughout the season, particularly after rainy or windy weather.

Go earlier in the season for apples. Different varieties ripen at different times, so check the orchard’s website to see what is currently available.

Save room for the cider donuts. No fall orchard trip is complete without them.

Make a day of it. Many of these farms offer markets, corn mazes, hayrides, animals and other seasonal activities, so there’s no need to stop after filling your basket.

Whether you’re looking for a quick afternoon close to home or a scenic fall day trip, these orchards and farms offer plenty of ways to enjoy the season just beyond Greenwich.

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