Apple picking, pumpkin patches, wagon rides and fresh-baked treats, fall farm season is almost here.
One of the best things about living in Milton is just how many farms and orchards we have close to home. You can spend a September afternoon picking apples, come back in October for pumpkins or make a full day of it with farm animals, corn mazes, wagon rides and all those fall treats we wait for all year.
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Whether you are planning a family outing, a fall date or simply want to bring home a bag of freshly picked Ontario apples, here are some of the farms worth adding to your 2026 Milton fall bucket list.
Chudleigh’s Entertainment Farm
Location: 9528 Regional Road 25, Milton
Apple Picking Begins: August 27, 2026
Peak Apple Season: September & October
Farm Hours: Currently listed as 10:00 a.m.–6:00 p.m. daily
Admission: Advance online ticket required
Chudleigh’s Entertainment Farm is probably one of the best-known fall traditions around Milton.
The farm has more than 47,500 apple trees across 60 acres, with over 18 varieties available throughout the harvest season. Early apples begin in late August, while September and October are the heart of apple-picking season.
But apples are only part of the experience.
There is also a pumpkin patch, tractor wagon rides, farm animals, a nature trail and a children's play area, making this an easy place to turn apple picking into a full fall outing.
Chudleigh’s uses three-hour timed admission, and tickets need to be purchased online in advance. Apple varieties ripen at different times, so check the picking schedule before choosing your visit.
Plan Your Visit: Chudleigh’s Fall Apple Picking & Schedule
Andrews Farm Market & Winery
Location: 9365 10 Side Road, Milton
2026 Season: May 30–November 1
Hours: 10:00 a.m.–4:30 p.m. daily
Fall Highlights: Pick-your-own produce, pumpkins, farm activities & Haunted Forest
Andrews Farm Market & Winery is another Milton-area farm that makes it easy to spend an entire fall afternoon outside.
The farm's pick-your-own program runs throughout the growing season, ending with fall pumpkins. General admission is required to access the picking fields, and anything you pick is purchased separately.
There are also plenty of other reasons to visit, including tractor rides, a playground, farm animals, corn and sunflower mazes and the Haunted Forest in the fall.
Because picking conditions can change quickly, Andrews recommends checking its latest crop updates before visiting if you have something specific in mind.
Plan Your Visit: Andrews Farm Pick-Your-Own Information
Springridge Farm
Location: 7256 Bell School Line, Milton
Hours: 9:00 a.m.–5:00 p.m. daily
Fall Produce: Apples, pumpkins, gourds, corn stalks & more
Springridge Farm is another local favourite when fall arrives.
September typically brings apples, corn, pumpkins and gourds to the farm, while October continues with apples, pumpkins and gourds along with corn stalks and hay bales.
This is a particularly good stop if you want the fall-farm atmosphere along with a visit to the barn market and bakery.
One thing to know before visiting: Springridge's seasonal produce list represents what is typically in season and does not guarantee availability on a particular day. Check with the farm if you are making the trip for something specific.
Plan Your Visit: Springridge Farm
Williams’ Orchards
Location: 10101 Hume Court, Milton
Fall Weekdays: Ready-picked fruit only
Fall Saturdays & Sundays: Ready-picked + pick-your-own
Hours: 9:00 a.m.–4:00 p.m.
2026 Fall Opening: To be announced
If you want a more traditional apple-picking experience, Williams' Orchard is worth knowing about.
This family-run Milton orchard has been operating since 1983 and grows apples, pears and plums.
Unlike some of the larger fall attractions, Williams’ keeps things fairly simple. There is free admission and free parking, although the orchard requires a minimum $25 purchase per family of five for entry to the orchard.
During the fall, pick-your-own is offered on Saturdays and Sundays, while weekdays are for ready-picked fruit. No appointment is required.
There is also a barn with seasonal ready-picked fruit, local honey and non-alcoholic apple cider.
Planning note: Williams’ has published its fall hours but has not yet announced the exact 2026 fall opening date, so check the website before heading out.
Plan Your Visit: Williams’ Orchards
A Little Farther From Milton
If you do not mind a drive, there are some great fall farms around Caledon and Hamilton that are close enough for a weekend day trip.
Downey’s Strawberry & Apple Farm – Caledon
Location: 13707 Heart Lake Road, Caledon
Apple Picking Opens: August 14, 2026
Hours: 9:30 a.m.–5:30 p.m. daily
Last Field Admission: 5:00 p.m.
Downey's Strawberry and Apple Farm has already published a detailed 2026 apple-picking schedule.
Apple picking begins August 14 with Ginger Gold apples, followed by other varieties as the season progresses. McIntosh is scheduled to begin around September 10 and Cortland around September 16.
The farm is open daily during apple season from 9:30 a.m. until 5:30 p.m., with the last admission to the fields at 5:00 p.m.
No reservations are required for apple picking.
Plan Your Visit: Downey’s 2026 Apple Picking Schedule
Downey’s Farm – Caledon
Location: 13682 Heart Lake Road, Caledon
Pumpkinfest Transition: After September 18, 2026
Fall Field Trips: September 23–October 30, 2026
Right across the road is Downey's Farm Market, home to one of the area's bigger fall farm experiences.
Downey's regular Farmyard Play Area runs through September 18 before transitioning into its Pumpkinfest Play Area for fall. The farm offers more than 40 activities, along with wagon rides, farm animals and seasonal food.
This is a good option if your fall outing is less about simply grabbing a pumpkin and more about making a full family day of it.
Planning note: The farm has confirmed its transition to Pumpkinfest after September 18, but check the official site for the final 2026 Pumpkinfest calendar and fall admission times before visiting.
Plan Your Visit: Downey’s Farm
The Apple Orchard – Hamilton
Location: 1668 Highway 6, Hamilton
2026 Season Opening: August 2026
Last Entry: 4:00 p.m. when operating
Last Wagon Ride: 4:00 p.m.
If you are willing to head a little south of Milton, The Apple Orchard Inc offers both apples and pumpkins along with a long list of family activities.
The orchard has more than 10,000 apple and pear trees and offers pick-your-own apples, wagon rides, animals, sunflower fields, a corn trail or maze, walking trails, a hay barn and other activities.
There is also a pumpkin and squash patch with more than 20 varieties. Some varieties can be ready as early as mid-August, although the exact timing depends on the crop.
The orchard has confirmed that its 2026 season opens in August, but its website is currently showing the farm as closed while it prepares for opening. That means I would not publish fixed September/October operating days yet. Check the website for updated fall hours before making the drive.
Plan Your Visit: The Apple Orchard
Quick Guide: Which Fall Farm Should You Choose?
For the classic Milton apple-picking experience: Chudleigh’s
For pick-your-own pumpkins: Andrews Farm
For a traditional, no-frills orchard: Williams’ Orchards
For a farm market, bakery and fall atmosphere: Springridge Farm
For a detailed 2026 apple-picking schedule: Downey’s Strawberry & Apple Farm
For a big family Pumpkinfest experience: Downey’s Farm
For apples, pumpkins and lots of farm activities in one visit: The Apple Orchard
When to Go๏ปฟ
Mid-to-Late August: Early apple varieties begin appearing at local orchards.
September: This is prime apple-picking season around Milton. It is also a great time to visit before the busiest October weekends.
Late September: Pumpkin season starts taking over, and fall farm festivals and attractions begin ramping up.
October: Pumpkins, gourds, apples, corn mazes and Halloween activities make this one of the busiest times of the year at local farms.
Before Halloween: Make that final pumpkin run before October 31.
Tips for Visiting Milton-Area Fall Farms
Fall farms can get very busy on sunny September and October weekends, so plan ahead.
Check the farm's website on the morning of your visit, especially if you are going specifically for apple or pumpkin picking. Crops are weather-dependent, and a variety that was available earlier in the week can sometimes be picked out by the weekend.
For farms that use timed admission, book ahead. And remember that admission and pick-your-own produce are often separate costs.
Most importantly, give yourself time to enjoy the experience. Half the fun is the wagon ride, wandering through the orchard, grabbing a fall treat and finding that one pumpkin everyone agrees is coming home.
Make Fall a Local Tradition
Living in Milton means some of Ontario's best fall experiences are practically in our backyard.
You can pick apples at a family-run orchard, spend an afternoon searching for the perfect pumpkin, take the kids to a farm festival or simply stop by a local market for fresh apples and something warm from the bakery.
And with so many farms close to home, there is no reason to fit everything into one weekend.
Pick a farm, grab your favourite sweater and start checking off that Milton fall bucket list.
Flowers Team Real Estate loves sharing the local businesses, events and seasonal traditions that make Milton such a great community to call home. Keep following along for more local guides, community events and things to do in and around Milton.
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