If you want to pick Virginia apples this fall, plan on late August through October for most orchards, with the Shenandoah Valley, Central Virginia and higher-elevation Southwest Virginia generally offering the longest and most dependable seasons.

I grew up in the Shenandoah region, so fall in Virginia has always meant apples to me: muddy shoes, a paper bag getting heavier by the row, cider donuts on the ride home and that particular smell of an orchard when the days finally turn cool. Now, as an environmental science educator, I look at those same orchards a little differently. An apple orchard is a living system—soil, pollinators, weather, elevation, water and farmers all working together—and every year’s harvest tells us something about the growing season.

That matters especially in 2026. A severe spring freeze damaged apple crops across Virginia, with some Northern Virginia orchards reporting little or no pick-your-own crop. Conditions vary dramatically from farm to farm, however, and Central and Southwest Virginia have generally fared better. Check an orchard’s availability before making a special trip.

Northern Virginia

Northern Virginia usually gets the apple season moving in late August, but this is the region where I’d be especially careful in 2026. Spring frost hit many orchards hard, and several normally popular pick-your-own farms are selling pre-picked apples instead this year. 

• Hartland Orchard — Markham: Typically opens late August to early September. Apples are generally sold by bag, rather than strictly by the pound. The orchard is a relatively relaxed family stop, but expect grass, uneven ground and walking between rows; I’d call it stroller-friendly with caveats, particularly for an all-terrain stroller. 
• Great Country Farms — Bluemont: Normally starts apple picking around late August, with apple prices varying by variety and charged by the pound after admission. The orchard is reached on foot rather than by car, so a stroller can work on the farm’s accessible areas but isn’t ideal for every orchard row. 
• Marker-Miller Orchards — Winchester: Typically opens in late August or early September and is one of the area’s classic family orchard destinations. Normally, apples are picked into orchard containers rather than simply paying a per-pound field price. Its extensive family facilities make it one of my better choices with young children, although orchard rows themselves can still be uneven. Important 2026 note: Marker-Miller is not offering apple pick-your-own this year because of weather damage, though pre-picked apples are available.

Local educator’s tip: In a normal year, Northern Virginia is a great place to compare early-season varieties. In 2026, however, I’d call before driving out expecting a full U-pick experience.

Richmond Metro

The Richmond region isn’t Virginia’s traditional apple heartland, so the selection is more limited. If you’re looking specifically for apple picking, I’d look beyond the immediate city rather than assuming every fall farm offers apples.

• Chesterfield Berry Farm — Moseley: Its fall season typically begins around mid-September, but the farm’s current 2026 fall program emphasizes pumpkins and farm activities rather than a major apple U-pick. Apples are not currently advertised as a principal 2026 pick-your-own crop. Strollers are generally workable around the farm attractions, but fields and festival areas can be rougher terrain. The farm accepts cash and cards.
• Agriberry Farm and CSA — Hanover: Apples are among the farm’s crops, but its public pick-your-own programming is more focused on berries and special harvest events than a traditional apple-picking operation. I’d treat it as a check-before-you-go option rather than a guaranteed apple U-pick destination.

For Richmond families, I’d consider this region the “farm fall” option rather than the apple-orchard capital. If apples are the entire mission, keep driving west.

Charlottesville and Central Virginia

This is where the landscape begins to look like the Virginia apple country I remember: Blue Ridge foothills, rolling orchards and farms where apple season overlaps with pumpkins, cider and changing leaves.

• Carter Mountain Orchard and Country Store — Charlottesville: The classic. A typical season gets going in late August or early September, with different varieties ripening through fall. Apples are generally purchased through prepaid picking containers/bags, rather than simply paying by the pound. The mountain setting means uneven terrain, so I would call it stroller-friendly around the market but not ideal in the orchard rows. No cash-only warning. Check the ripening schedule before visiting.
• Chiles Peach Orchard and Farm Market — Crozet: Normally starts apples around late August/September. In 2026, weekend apple-picking passes are scheduled for October weekends, while weekday picking is available without the weekend pass when conditions permit. You pay for the orchard container, rather than by pound. Not stroller-friendly in the picking fields—the farm specifically restricts strollers in the fields. 
• Fruit Hill Orchard — Palmyra: Typically gets into apples from late summer into fall. You pay for what you pick using the farm’s containers, with no separate picking fee. Terrain is more natural and uneven, so I’d rate it limited for strollers. 
• Dickie Brothers Orchard — Roseland: A quieter, old-fashioned orchard experience that generally comes into its own in September. Pricing and U-pick availability vary by season, so check before going. The orchard is not a stroller-first environment; think working farm rather than paved attraction.

Shenandoah Valley

This is home territory for me, and it remains one of Virginia’s best places to experience apple country. Virginia’s apple production is heavily concentrated through the Shenandoah Valley and toward the Roanoke area.

• Showalter’s Orchard & Greenhouse — Timberville: Typically begins late July or early August, with varieties continuing into fall. Apples are generally picked into bags/containers, rather than sold strictly by the pound. The farm is family-friendly, but orchard ground is still orchard ground: stroller-friendly around the market, less so between trees. 
• Marker-Miller Orchards — Winchester: Normally opens in late August/early September, with a particularly strong family-farm atmosphere. 2026 is the exception: no apple U-pick because of crop damage, although pre-picked apples remain available.
• Mackintosh Fruit Farm — Berryville: Typically starts apple picking in August and continues into October. The farm has traditionally charged by the pound for produce picked, with free entry. Orchard terrain makes this limited for strollers. In 2026, availability is particularly important to verify because of the spring freeze.

If you’re teaching children about agriculture, this is the region I’d choose. You can talk about elevation, frost pockets, pollination, harvest timing and how the same species responds differently across a landscape. It’s the kind of hands-on outdoor learning that carries straight into summer, and we’ve collected more of those conversation starters in our parent resources.

Hampton Roads and Tidewater

Apple country gets trickier as you move toward sea level, but there are still a few family farms worth watching.

• Cullipher Farm — Virginia Beach: Typically gets its fall apple season going around late August into September. In 2026, pick-your-own apples and Asian pears have been offered at $25 per peck, making this a per-bag/container model rather than per pound. The farm is family-oriented, but field conditions mean I’d call stroller use limited once you’re beyond the market.
• Mount Pleasant Farms — Chesapeake: A family farm with seasonal U-pick programming, though apples are not as consistently promoted as its berries and peaches. Typical fall activity begins around September. Treat apple availability as check-first, and expect natural farm terrain rather than paved orchard paths.

Tidewater’s apple season can feel shorter and less predictable than the mountain regions, so don’t wait until late October if apples are your goal.

Southwest Virginia

For both scenery and agricultural education, Southwest Virginia is one of my favorite parts of the state. Higher elevations can create cooler growing conditions, and the region has a long apple-growing tradition.

• Gross Orchard — Bedford: Apple picking typically begins around September 1 and continues as varieties ripen through fall. This is a per-bag system: choose a bag, prepay, then fill it. The fields are open for walking, but I’d rate stroller access limited to moderate because you’re dealing with orchard terrain. No cash-only warning is published.
• Wade’s Orchard — Woolwine: The farm’s apple season begins with early varieties in July, moving through Gala and Honeycrisp in August and later varieties in September and October. Fruit is sold by the pound, bag, bushel or truckload, depending on what you’re buying. Wade’s Orchards. This is primarily a farm stand rather than a conventional public U-pick orchard, so stroller access is generally easier at the stand than in production areas.
• Johnson’s Orchard — Bedford: A large, family-oriented orchard operation with U-pick fruit traditionally running through June–October, including apples. Expect a working-farm environment, so a sturdy stroller is preferable to a lightweight umbrella stroller. Availability can be highly weather-dependent.

Apple Season Timeline

One reason I tell people not to think of “apple season” as a single weekend is that Virginia’s harvest is a relay race.

• Late July–August: Early apples such as Ginger Gold and Gala begin appearing, especially in warmer or lower-elevation orchards.
• September: This is the heart of the season. Expect Gala, Golden Delicious, Empire, Red Delicious, Honeycrisp and many regional varieties.
• Early October: Later varieties—including Granny Smith, Fuji and Winesap—start taking over.
• Mid-to-late October: Look for Fuji, Winesap, Arkansas Black and other late-season apples, particularly in Southwest and mountain orchards.
• November: U-pick opportunities become less common, but late apples, cider and pre-picked fruit can continue into early November or beyond at some farms. Virginia’s overall apple harvest can extend into early November.
• And one final rule from both my childhood and my environmental-science classroom: never assume an orchard is open just because the calendar says apple season. Weather changes ripening dates, frost can eliminate a crop, and a busy Saturday can clean out a variety faster than you expect. Call or check the farm’s same-week update before you go—and bring cash unless you’ve confirmed cards are accepted. In 2026 especially, that five-minute check can save you a long drive and help support the farms that are navigating an unusually difficult growing season.

Make a Day of It

An orchard trip pairs well with the rest of a Virginia fall. If you’re building a whole outdoor weekend, the Virginia Department of Wildlife Resources maintains trail and wildlife-viewing information for every region on this list, and the Virginia Department of Agriculture and Consumer Services keeps a statewide list of farms and seasonal availability worth bookmarking. You might also enjoy a paddle, splashing in a creek or rock collecting too! 

And if all this fresh air has your kids asking what’s next, fall is when a lot of Virginia camps open registration for summer. Our camp directory covers more than 200 day camps, overnight camps and specialty programs across the state, including plenty of nature and farm programs in these same regions. You can also grab our free planning downloads or sign up for the newsletter so seasonal guides like this one land in your inbox.

Before You Go

One final rule, from both my childhood and my environmental science classroom: never assume an orchard is open just because the calendar says apple season. Weather changes ripening dates, frost can wipe out a crop, and a busy Saturday can clear out a variety faster than you’d expect.

Call or check the farm’s same-week update before you go, and bring cash unless you’ve confirmed cards are accepted. In 2026 especially, that five-minute check can save you a long drive and help support the farms navigating an unusually hard growing season.