Thomas Jefferson once accepted part of a mountain as payment for legal work. Today, that same mountain is covered in apple trees you can pick yourself.
I love that a lawyer’s fee eventually turned into pie.
The history only gets deeper from there. One family on this list has farmed the same Virginia land since 1819.
Another farm has grown apples for sale since the 1890s.
I can’t think of a better reason to skip the grocery store bin. Buying straight from the growers means fresher fruit and a real person behind it.
Many of these farms let you pick your own, too. A few also sell peaches and apples already picked and waiting.
Then there are the extras, like cider donuts, slushies, pies, and peach ice cream. So grab a bag and a napkin.
Which orchard is calling your name first?
1. Carter Mountain Orchard and Country Store
Few orchards can say Thomas Jefferson once owned part of the hill, but this one sits on exactly that kind of land. Jefferson received a piece of it in 1771 as payment for legal services.
Monticello still owns property right next door. The Chiles family started running it as a commercial apple orchard in the early 1970s and bought the land in 1985.
Up at 1,120 feet, the views stretch across Charlottesville, the Piedmont, and the Blue Ridge Mountains. You’ll want your camera out before you even grab a picking bag.
Blackberries kick things off in early June, with peaches following in July and August. Look for white, yellow, and flat donut peaches during that summer stretch.
Apple season runs from mid-August through November. The lineup includes Albemarle Pippin, Jonagold, Pink Lady, CrimsonCrisp, Candy Crisp, and plenty more.
Not in a picking mood? The country store sells fruit already picked, plus apple butter, jams, fruit syrups, and pancake mixes.
Then comes the bakery, added in 1995 and famous for apple cider donuts made daily. Pair one with fresh-pressed cider, a cider slushie, or a donut sundae if you’re feeling bold.
Homemade apple, peach, and cherry pies are also on the menu. Soft-serve ice cream rounds out the sweet stuff nicely.
Plan ahead for fall weekends from mid-September to mid-November, when visitors 12 and up need entry passes. On those days, a drive-thru option lets you shop without a pass.
Thursday evenings from April through September bring the Sunset Series with live music and food trucks. Pets aren’t allowed, so leave the pup at home.
Address: 1435 Carters Mountain Trail, Charlottesville, VA 22902
2. Mackintosh Fruit Farm
Short trees make for happy pickers, and this Berryville farm grows dwarf trees that put fruit within easy reach. Kids can grab their own apples without anyone hoisting them up.
The family has run the farm since 1988, and the picking calendar is impressively long. Strawberries arrive in May, sweet cherries in June, and blueberries peak that same month.
Raspberries and blackberries fill July and August alongside peaches and nectarines. Pears and apples like Jonagold, Criterion, and Honeycrisp take over in September and October.
You can even find pawpaws here, a native fruit that rarely shows up in stores. Quantities can be limited, so calling ahead is a smart move.
Picking tools and wagons help you haul your harvest back to the car. Sunflowers, zinnias, tomatoes, peppers, and other vegetables are ready for picking too.
Once your arms get tired, head to the kitchen for paninis, wraps, pulled pork, burgers, or a zucchini pizza. Covered open-air seating gives you a shady spot to eat.
Save room for baked cider donuts, handmade fruit pies, cobblers, and homemade ice cream. Fresh-pressed apple cider is a fine way to wash it down.
The market sells honey from the farm’s own bees, along with preserves, local cheeses, grass-fed meats, and free-range eggs. Local art and handcrafted items fill out the shelves.
Little ones can burn energy at the playground and sandbox or say hi to the ducks on the pond. Entrance and parking are free, and leashed dogs are welcome.
The farm opens Thursday through Sunday from May through October. Mondays through Wednesdays, the trees get a break.
Address: 1608 Russell Road, Berryville, VA 22611
3. Stribling Orchard
Apples have grown on this Markham land since before America was a country. The property was part of a 1733 land grant, and the main house dates to the mid-1700s.
The Stribling family bought the place in 1819 and still farms it today. After World War II, a family member started the pick-your-own idea that still runs today.
More than 2,500 apple trees cover the rolling hills here. Varieties include Honeycrisp, McIntosh, Fuji, Cortland, Stayman, and Winesap, among others.
Peaches and nectarines open the season in July, with peach picking running through mid-August. Popular apples can get picked over early on weekends, so arrive early.
Fun twist: you can drive your car right through the orchard. If you’d rather stroll, a 3/4-mile path works too.
Picking bags and poles are provided, which helps with those high branches. Pumpkins come from the patch in fall, with extra pre-picked ones on hand.
Starting in September, the bakery opens on weekends with pies and pastries. The fresh apple pie follows a family grandmother’s recipe, and apple raisin swirl bread is another treat.
The store sells beef raised on the farm, plus cider, jams, fruit butters, sauces, and honey from the orchard’s own hives. Local eggs and cheeses are there too.
Horses, donkeys, goats, sheep, and pigs live on the property. Hilltop picnic spots look out over the valley toward the Blue Ridge Mountains.
Fall weekends usually bring live music and vendors selling lunch, ice cream, and kettle corn. The farm is generally open July through October, closed Mondays and Tuesdays.
Address: 11587 Poverty Hollow Lane, Markham, VA 22643
4. Marker-Miller Orchards
Winchester hosts the Shenandoah Apple Blossom Festival each spring, so apples are kind of a big deal here. This family-friendly orchard lets you get your hands on them straight from the branch.
Pick-your-own is the main event, and the apple selection is wide. You’ll find plenty of different kinds to fill your bag, so bring an open mind.
Not sure which variety to grab? Mix a few and turn your kitchen into a taste test later.
The store deserves its own trip, packed with farm fresh items and fresh baked goods. Expect to leave with more than you planned.
Then there are the cider slushies, an icy treat that makes a hot picking day feel easier. Grab one before you head out to the rows, or save it as a reward.
Kids get a free playground, which is handy when little legs need a break from picking. It also gives grown-ups a minute to sort through the haul.
Restrooms and a free parking lot make the visit simple. You won’t have to hunt for a spot or wander far.
Saturdays bring the biggest crowds, especially from morning into the afternoon. Weekday visits from Monday through Thursday tend to be calmer if you like space.
Hours run 11 AM to 4 PM Monday through Thursday and Sunday. Friday and Saturday open earlier at 10 AM and stay open until 5 PM.
The orchard sits on Cedar Creek Grade in Winchester, in the heart of Virginia’s apple region. Toss a cooler in the trunk so your apples and baked goods ride home happy.
Address: 3035 Cedar Creek Grade, Winchester, VA 22602
5. Showalter’s Orchard & Greenhouse
Cider presses have been squeezing apples on this Timberville farm since 1975. Before that, apple trees had already covered the property since the early 1900s.
The family started farming here in 1965 and opened a fresh market. Greenhouses went up in 1972, and later generations keep the tradition alive.
With more than 30 apple varieties, picking here can feel like a treasure hunt. Look for Lodi, Summer Rambo, Ginger Gold, Jonagold, Rome Beauty, York, and Pink Lady.
Apple season usually runs from mid-July through November. Pick-your-own peaches typically start around the first week of August, with Sweet-N-Up and Summerfest leading the way.
Picking bags are supplied, and no reservations or tickets are generally needed. A smart move is grabbing a small bag to pick, then buying seconds apples in the market.
Seconds may have a few cosmetic flaws, but they’re budget-friendly and still full of flavor. They’re perfect for sauce, pies, or snacking on the ride home.
The famous sweet apple cider is pressed right on the farm, usually arriving around early September. On hot days, a sweet cider slushie hits the spot.
Apple cider donuts are another reason to linger. The market also stocks Virginia food products, handmade soaps, and local crafts.
Step outside for 360-degree views of the Shenandoah Valley with a peek at the Blue Ridge. Don’t miss the LOVE sign made from apple wood and stainless steel.
Fall Saturdays in September and October bring food trucks and live music. Dogs are welcome, so your four-legged sidekick can tag along.
Address: 17768 Honeyville Rd, Timberville, VA 22853
6. Chiles Peach Orchard and Farm Market
If the Chiles name sounds familiar, you may already know their mountain orchard near Charlottesville. This Crozet farm comes from the same family, with a peachy twist.
Peaches sit right in the name, and they’re a big part of the summer fun. You can pick them yourself or buy them ready-picked in the farm market.
The season stretches from April through December, which is longer than you might expect. Strawberries and blueberries show up first, then peaches, apples, and pumpkins follow in season.
Blue Ridge Mountain views surround the orchard, giving your picking trip a scenic backdrop. Downtown Crozet is within easy reach, so you can make a day of it.
Choosing between picking and buying is half the fun. Pickers get the thrill of the hunt, while ready-picked fruit is perfect for busy schedules.
Inside, the Farm Market and Bakery is stocked with favorites to take home. Ice cream is on hand too, which feels like a must after picking peaches in the sun.
The farm also keeps a festive calendar of events throughout its season. Check the schedule before you go so you can match your visit to the fun.
Hours run 9 AM to 6 PM, seven days a week. That makes it easy to fit in a weekday trip or a lazy Sunday outing.
Peaches change quickly through the summer, so texture and juiciness can vary by week. Giving fruit a gentle squeeze before filling your bag is always a good idea.
Free parking makes arriving simple. Pack a cooler for the drive home, and your Virginia peaches will thank you.
Address: 1351 Greenwood Rd, Crozet, VA 22932
7. Drumheller’s Orchard
Raw cider is getting hard to find, but this Nelson County orchard still crushes and squeezes apples weekly each fall for sweet, unpasteurized cider. That alone is worth the trip for cider fans.
The farm dates to 1937, when the family first acquired the land. Today it’s a fifth-generation operation, and the original packing shed went up in the early 1940s.
Season kicks off in mid-May with blueberries and ends in December with apples. In between, you’ll find peaches, blackberries, plums, and pluots.
Summer brings pick-your-own blueberries and blackberries. Apples come in 21 types, including Winesap, Black Twig, Arkansas Black, Fuji, and Pink Lady.
Third and fourth generation farmers make the baked goods, jams, and butters from scratch in the on-site kitchen. Peach, blueberry, and blackberry pies are just the start.
Apple cider donuts, including a pumpkin spiced version, are a fall favorite. Blueberry donuts, banana peach bread, and handcrafted caramel apples keep the sweets coming.
Soft serve comes in peach and vanilla, and apple cider slushies cool you down fast. Peach jam and peach butter make easy souvenirs.
Fall festival weekends add hayrides to a pumpkin patch and corn maze. There’s also an apple slingshot, which is exactly as fun as it sounds.
Live music, local vendors, and a kids’ zone round out those festival days. The farm is pet friendly, so the family dog can join the outing.
Live too far away? The orchard ships apples nationwide and attends farmers markets in Richmond and Williamsburg.
Field trips and bus tours are offered as well, with scheduling beginning in August. Teachers, take note.
Address: 1130 Drumheller Orchard Lane, Lovingston, VA 22949
8. Gross Orchard
Early birds, this one’s for you, because the doors open at 8 AM Monday through Saturday. That gives you a head start before the afternoon sun heats up the rows.
Gross Orchard is a family-owned operation in Bedford, near the Blue Ridge Mountains. It pairs pick-your-own fruit with a country store full of homemade goods.
Apples and peaches are the stars of the u-pick show. The selection gives you plenty of options, so you can wander the rows and find your favorites.
Rather skip the picking work? You can simply shop in the country store instead, and nobody will judge.
Homemade goods share space with fresh fruit on the shelves. It’s an easy way to bring a little farm flavor home without breaking a sweat.
Saturdays draw the biggest crowds, from morning into the afternoon. For a calmer trip, try Tuesday through Thursday, when things tend to be much quieter.
Remember that the orchard is closed on Sundays. Plan a Saturday visit early or make it a weekday adventure.
A visit here usually doesn’t take long, which makes it a smart stop on a day trip. Restrooms are available, a nice bonus after a long ride.
Bedford County’s rolling countryside makes the trip part of the fun. Roll down the windows and take your time getting there.
Bring a sturdy bag or box for your haul, since fresh peaches bruise easily. Apples travel better, so stack them on the bottom.
Buying from a family grower in Virginia also keeps your money close to the farm. That’s a sweet deal for everyone involved.
Address: 6808 Wheats Valley Rd, Bedford, VA 24523
9. Morris Orchard
Apples have been grown for sale at this Monroe farm since the 1890s. That’s well over a century of practice, and it shows in the variety.
Morris Orchard is a family-owned Virginia Century Farm at the base of High Peak Mountain. A log cabin on the property dates back to the early 1800s.
Blueberry picking runs from mid-June to early July. Thornless blackberries take over from mid-July to late August, so no scratched arms.
Pre-picked peaches arrive mid-June and last into mid-August. Varieties include Red Haven, Belair, Blake, and the classic Elberta.
Pick-your-own apples aren’t offered this season because of crop size. Still, the farm store sells fresh-picked GoldRush, Arkansas Black, Crispin, York, Black Twig, and more.
October weekends bring apple cider donuts, and fresh apple cider flows from mid-September to December. Apple butter, local honey, jams, and jellies make tasty take-home gifts.
Come fall, you can pick pumpkins straight from the patch. The store also carries gourds, specialty pumpkins, and butternut squash.
Kids will love the petting zoo and hay creations dressed up with Halloween decorations. Picnics are welcome near the hay displays, though not in the orchard itself.
Want to stay longer? The renovated 1930s Orchard Farmhouse welcomes pets, while the early 1800s Moes’ Cabin does not.
Both stays include full kitchens, fire pits, pond access, and mountain views. That means you can bake a pie with apples bought that morning.
Picking bags are provided, and personal bags or coolers stay out of the orchard. Climbing trees and tossing apples are off the menu too.
The farm usually closes from January through March, so plan accordingly.
Address: 226 Tobacco Row Lane, Monroe, VA 24574
