Pumpkin Paradise: Best Pumpkin Patches Near Winchester
When the Shenandoah Valley shifts into autumn, Winchester truly comes alive. The air turns crisp, the trees ignite with red and gold leaves, and the scent of apple cider drifts from local farm markets. If you’re looking for the perfect way to spend a fall weekend, you can’t beat a visit to a pumpkin patch.
From quick afternoon outings to day-long fall festivals, the area around Winchester offers everything from charming local farms to regional destinations packed with autumn activities. Whether you’re planning a family trip, a date day, or a friends’ fall adventure, this guide will help you find your perfect patch.
In This Article
- Closest Pumpkin Patches to Winchester
- Marker-Miller Orchards
- Hill High Farm
- Wayside Farm Fun
- Worth-the-Drive Fall Favorites
- Cox Farms
- Round Hill Farm
- Graves Mountain Farm
- Tips for Visiting Pumpkin Patches
Closest Pumpkin Patches to Winchester
Marker-Miller Orchards
Winchester, VA — about 10 minutes away from Downtown Winchester
This Winchester staple is practically a fall tradition. While it’s famous for its apples, Marker-Miller offers a sweet little pumpkin patch each autumn. And don’t miss their fall festivals:
Apple Harvest Festival – Expect pick‑your‑own apples, homemade apple cobbler, cider, turnovers, apple pie ice cream, and those famous apple cider donuts. There will be live music, local food vendors—including Blue Ridge Bar‑B‑Q and 3 Fires Oven Pizza—and family delights like the cow train and scenic wagon rides.
Pumpkin Festival – Visitors can “find the great pumpkin”—either pick one or choose from those already gathered. The farm bakery offers seasonal treats like pumpkin pie, rolls, bars, and donuts. Expect crafts, food stalls (same local favorites), plus the cow train and wagon rides to round out the experience.
Hill High Farm
Winchester, VA — about 15 minutes from Downtown Winchester
A beloved fixture of Winchester for over 100 years, Hill High Farm invites families to embrace fall with full sensory delight. The Pumpkin Patch here features not just pumpkin picking but also daytime and moonlit hayrides, a petting zoo, a large corn maze, and even a straw maze packed with free children’s activities. Visitors often rave about the farm’s cozy bluegrass music setting, homemade comfort food, and nostalgic farm atmosphere—making it a genuine Shenandoah Valley escape just minutes from home.
Wayside Farm Fun
Berryville, VA — about 25 minutes away from Winchester
This 120‑acre family farm brings a sense of wonder to the season. Opening its gates for fall in September and running through November, it offers a wide variety of experiences, from pick‑your‑own pumpkins, a sprawling corn maze, and pig races, to barnyard activities and photo-ready scenes across the grounds. It’s the kind of place that’s perfect for a fun outing with kids—bringing energy and charm to every visit.
Worth-the-Drive Fall Favorites
Cox Farms
Centreville, VA — about 1 hour from Winchester
By day, Cox Farms delivers one of Northern Virginia’s biggest fall festivals—with giant slides, hayrides, farm animals, the whimsical Cornundrum, and flavorful fall treats (think kettle corn, cider, and donuts). But when night falls, the farm transforms into a spine‑tingling haunted experience for brave souls.
Fields of Fear covers over 20 acres of nighttime terror. Included in the ticket are:
- The Forest: Back 40 — a half‑mile plunge through woods haunted by chainsaws, spiders, and unsettling surprises.
- Cornightmare — a corn‑maze nightmare full of jump scares and eerie theatrics.
- Dark Side Hayride — a haunted wagon ride through twisted, circus‑like landscapes.
- The Firegrounds — a fiery refuge with bonfires, karaoke, a six‑lane slide, and more—is perfect for catching your breath between scares.
Round Hill Farm
Culpeper, VA — about 90 minutes away from Winchester
This scenic destination offers a classic countryside autumn experience. Visitors can enjoy tractor-drawn hayrides to the pumpkin patch, pick their own pumpkins or choose from ones at the farm market, then explore the barnyard petting zoo, corn maze, pony rides, and vibrant mums. It’s a nostalgic, relaxed way to soak in fall—and a smart escape into Virginia’s rolling landscapes.
Graves Mountain Farm
Syria, VA — about 90 minutes from Winchester
A true seasonal treasure, this farm hosts its Apple Harvest Festival on the first three weekends of October. The festival features crafts, hayrides, farm animals, live bluegrass music, apple butter made over an open fire, pony rides, and classic fall fare like fresh cider and donuts. It’s a full-on harvest celebration in the heart of the Blue Ridge Mountains.
Tips for Visiting Pumpkin Patches
Pumpkin patches are more than just a place to grab a gourd — they’re a seasonal experience. Here’s how to make the most of your trip:
Plan your drive home so your pumpkins and market finds stay fresh.
Start early to beat the crowds and enjoy cooler weather.
Dress in layers and go for fall colors — it’s practical and looks great in photos.
Wear comfy shoes that can handle a little dirt or mud.
Bring a tote bag for smaller pumpkins and market goodies.
Check farm event calendars — special weekends often feature live music, food trucks, or themed activities.
Sample the local treats — fresh cider, apple butter, and pumpkin-flavored everything are part of the experience.
Why Fall is Special in Winchester
In Winchester, autumn is more than just a season — it’s a celebration. The city’s walkable downtown, lined with coffee shops and boutiques, makes for a perfect pre- or post-pumpkin patch stop. And with so many farms nearby, you can make fall traditions part of your everyday life.
🍂 Live in the heart of the action. At The Local in Winchester, VA, you’re just minutes from both downtown charm and countryside escapes, giving you the best of both worlds this fall.