One Virginia orchard has been run by the same family since 1819. That means its apple trees were being tended before most states even joined the country.
I love that kind of detail. It turns a simple bag of apples into a little piece of history you can carry home.
Other farms here go big in different ways, with pumpkin launchers, corn cannons, and patches growing more than 50 pumpkin varieties.
This list covers the coast, the mountains, and plenty of places in between.
Some spots lean toward quiet orchard rows. Others feel like a full festival with slides, hayrides, and cider donuts.
Consider this list your excuse to grab a sweater and hit the road. The only question is which one you’ll pick first, and whether you’ll stop at just one.
1. Cullipher Farm
Grapes, apples, and pumpkins all wait for your basket here in the fall. That’s a pick-your-own triple play, and it happens right in Virginia Beach.
Cullipher Farm has been family-owned since 2005. It sits on Princess Anne Road, far enough from the boardwalk to feel like real farm country.
Autumn is when the place really stretches its legs. You can wander the pumpkin patch, pull apples off the trees, and snip grapes straight from the vine.
Need a break between baskets? The bake shop handles fresh baked goods, and there’s ice cream and slushies too.
A food truck also adds more options for hungry pickers. That’s handy when the corn maze turns out to be trickier than expected.
Kids get a large playground area to burn off energy. Farm animals add another reason to linger a little longer.
The scenic farmland views are a nice surprise so close to the coast. Ocean breezes and pumpkin patches make a pretty fun combo.
Plan your visit for Tuesday through Sunday, since the farm closes on Mondays. Group tours and seasonal events also fill the calendar, so check ahead before you go.
Address: 772 Princess Anne Rd, Virginia Beach, VA 23457
2. Williams Orchard
Apples and pumpkins usually just sit there looking pretty. At Williams Orchard, they get launched.
The apple and pumpkin launcher is a big draw at this family-run farm in Wytheville. Watching produce sail through the air is oddly satisfying.
Once the launching fun wraps up, hop on a hayride. It’s a relaxed way to take in the Southwest Virginia countryside.
The pumpkins here earn plenty of love for their quality. Expect solid choices whether you want a carving giant or a tiny tabletop gourd.
Apples are the real anchor, of course. Some folks make this their one and only apple stop each fall, and it’s easy to see why.
Don’t skip the cider. It’s a sweet, simple reward after a day spent outdoors.
The farm store is worth a browse too. It’s a nice place to stock up before the drive home.
Wytheville sits near the crossroads of two big interstates. That makes the orchard an easy detour on a mountain road trip.
Plan around the hours, since the farm opens Monday through Saturday from 10 a.m. to 5 p.m. Sundays are closed, so save this one for a Saturday adventure.
Address: 5175 W Lee Hwy, Wytheville, VA 24382
3. Henley’s Orchard
Hot cocoa and cider donuts in the same trip? Crozet clearly knows how to treat apple pickers.
Henley’s Orchard sits west of Charlottesville, close to the Blue Ridge. It’s a pick-your-own apple spot with a big variety of tasty fruit.
The staff have a reputation for being kind and helpful. That’s a bonus if you can’t tell a Fuji from a Gala.
Beyond the trees, you’ll find pumpkins, gourds, and flowers. It’s an easy place to grab everything for a fall porch display in one stop.
Kids usually head straight for the petting zoo. Meanwhile, grown-ups can wander toward the cider.
There’s also a place to eat on site. Pair a snack with cider donuts and you’ve got a pretty good lunch.
Hot cocoa is a smart pick on chilly mornings. Holding a warm cup while staring at mountain views just feels right.
Timing matters here. The orchard closes Monday and Tuesday, opens Wednesday through Friday from 9 a.m. to 5 p.m., and weekends from 10 a.m. to 5 p.m.
Weekdays could be your sneaky move for a calmer orchard stroll.
Address: 2192 Holly Hill Farm, Crozet, VA 22932
4. Braehead Farm
Most farms take a winter nap, but this one keeps its gates open year round. Daily, too, which is a rare treat.
Braehead Farm is a full operating farm in Fredericksburg. It opens to the public every day from 9 a.m. to 6 p.m.
Fall is a big moment here. A hayride rolls you toward the pumpkin patch, where you get to hunt for your own pick.
Pumpkins aren’t the only thing on the menu. Seasonal fruits, vegetables, and flowers are also available for pick-your-own fans.
That makes it easy to leave with a whole autumn haul. A pumpkin for the porch, some flowers for the table, and maybe veggies for dinner.
Little ones can feed the farm animals, which is usually a highlight. The family playgrounds give them room to run afterward.
Picnic areas let you slow down and stay a while. Packing a lunch turns a quick pumpkin run into a full afternoon.
A farm market rounds things out for anyone who’d rather shop than pick. Dogs are allowed too, so your four-legged pal can tag along for the fun.
Fredericksburg history buffs can pair this stop with a stroll downtown.
Address: 1130 Tyler St, Fredericksburg, VA 22401
5. Morris Orchard
Sweet potatoes might be the sneaky star of an October trip to Monroe. Apples and pumpkins get top billing, but don’t overlook those orange spuds.
Morris Orchard is a family farm in Central Virginia, just north of Lynchburg. The address on Tobacco Row Lane hints at the area’s farming roots.
You can pick your own apples here. Pumpkins are also fair game for anyone hunting the perfect jack-o-lantern.
Feeding the animals is a fun break between picks. Kids especially love that hands-on moment.
Then there are the donuts. Pair them with a cup of the apple cider, which earns high praise from fall regulars.
Sweet potatoes make a smart souvenir for Thanksgiving planning. Toss a few in the trunk next to your pumpkins.
This stop feels simple in the best way. No giant festival, just good produce and a nice family farm setting.
Hours are generous, too. The orchard opens Monday through Saturday from 9 a.m. to 5 p.m., plus Sunday afternoons from 1 to 5 p.m.
That Sunday window works well after a slow morning. Sleep in, grab coffee, and still make it for cider.
Address: 226 Tobacco Row Ln, Monroe, VA 24574
6. Wayside Farm Fun
Over 50 pumpkin varieties grow in one field in Berryville. Choosing just one might be the hardest decision of your weekend.
Wayside Farm Fun lets you pick those pumpkins right from the vine. Warty, white, striped, or classic orange, you’ll have options.
The fall festival packs in a lot. There’s a huge corn maze, hayrides, farm animals, and jumping pillows.
Wear comfy shoes for the maze. A huge maze means plenty of wrong turns, which is half the fun anyway.
Hungry yet? Apple cider donuts are on the menu, and they’re a fan favorite here.
Many visitors save pumpkin picking for last. After a full day of fun, it’s a sweet way to wrap things up.
The farm sits close to Winchester, Leesburg, and Ashburn. That makes it a handy escape for Northern Virginia families.
Plan for Thursday through Sunday from 10 a.m. to 6 p.m. The farm closes Monday through Wednesday.
Free on-site parking makes arrival easy. Bring friends, since the jumping pillows are even better with a crowd.
Address: 5273 Harry Byrd Hwy, Berryville, VA 22611
7. Great Country Farms
A pumpkin-munching dinosaur named P-Rex lives in Bluemont. Honestly, that alone earns this farm a spot on your fall calendar.
The Zurschmeide family has farmed in Loudoun County since the 1970s. Great Country Farms itself got rolling in 1993 with a CSA program.
In autumn, a farm truck can carry you out to the pumpkin patch and apple orchard. You pick your own, which means you choose the perfect pumpkin, lopsided or not.
Then comes the 15-acre play area. Think jumping pillows, giant slides, a Farm Ninja Obstacle Course, and Cow Pie Putt-Putt Golf.
Weekends bring the Oinkintucky Derby Pig Races. Yes, real pigs, really racing, and yes, you should pick a favorite.
Cider pressing demonstrations show how apples become that sweet drink in your cup. Grab cider donuts afterward and find a spot near the fire pits.
Pumpkin cannons add a loud finale to the day. Goats and other farm animals keep things a bit calmer.
The Fall Pumpkin Harvest Festival runs from mid-September through October 31. The farm opens daily at 9 a.m., so early birds can beat the afternoon rush to the patch.
Address: 34345 Snickersville Turnpike, Bluemont, VA 20135
8. Stribling Orchard
Since 1819, one family has farmed this land. James Monroe was president when they got started.
Stribling Orchard sits on Poverty Hollow Lane in Markham. Today it raises pick-your-own peaches and apples.
Apple season is the fall headliner. Grab a bag, find a row, and start filling it with fruit grown on very historic ground.
Starting in September, the bakery opens on weekends. Pastries and pies are the reward for all that picking.
The farm store stocks apple cider, jams, butters, sauces, and honey. Pumpkins are available too, plus beef raised right on the farm.
Fall weekends get extra lively. Vendors usually offer lunch items, ice cream, and kettle corn.
Live music often plays on those weekends as well. It’s a nice soundtrack for a lazy afternoon in the orchard.
Dogs are allowed, so your pup can join the outing. Free parking keeps things simple.
The orchard is generally open July through October. Fall hours run Thursday through Sunday, from 9 a.m. to 4:30 p.m.
Address: 11587 Poverty Hollow Ln, Markham, VA 22643
9. Chesterfield Berry Farm
A corn cannon you can fire for free? Moseley is clearly not messing around.
Chesterfield Berry Farm is a family fun farm with seasonal festivals. It sits southwest of Richmond, an easy drive for city dwellers.
In fall, a hayride takes you down to the pumpkin patch. It’s practically required, and it’s a relaxing ride through the farm.
Sunflowers bloom nearby, which makes for great photos. Pumpkins plus sunflowers equals a very colorful picture.
Berry picking is part of the farm’s seasonal lineup too. The name gives that away, of course.
Tractor-train rides add another way to roll around the property. Corn mazes and the corn pit keep kids busy for a good while.
The animals are another favorite stop. Plan to spend more time there than you expect.
Save room for the pumpkin pie. The slices here are known for being huge.
Buying tickets online can lower your entrance fee. Hours run Thursday and Friday from 2 to 6 p.m., plus weekends from 9:30 a.m. to 5 p.m.
Address: 26002 Pear Orchard Rd, Moseley, VA 23120
10. Lloyd Family Farms
Fifty-plus acres of pumpkins is a lot of orange. Good luck leaving with just one.
Lloyd Family Farms is a family-run seasonal spot in Rockville, northwest of Richmond. Its huge patch is packed with home grown pumpkins and unique varieties.
Hayrides carry you out to the field. The farm also offers handicapped accessible trailers, so more people can join the ride.
Kids have plenty to explore. There’s a corn maze, a corn pit, a straw castle, a sand pile, and a giant jump pad.
Pony rides are a sweet bonus for young cowpokes. Yard games fill the play area too.
Barnyard animals round out the visit. Look for chickens, goats, horses, and a bull named Henry.
Local food trucks show up on weekends. Their schedule gets posted on social media, so peek before you go.
Children 2 and under get in free. Smoking isn’t allowed, and outside animals stay home, except service animals.
The patch opens Friday through Sunday from 9 a.m. to 5 p.m. during the season. It’s a fitting finale for your Virginia fall farm tour.
Address: 12204 Pinhook Rd, Rockville, VA 23146
