Fall is an amazing time to live in the Shenandoah Valley! Winchester is apple country, and fall is when we shine. The leaves change, the weather is perfect (some of the time, maybe), and there are pick-your-own apples and pumpkins everywhere you look. The abundance of fall festivals are great for family fun, and even better for family photo ops! (My kids get matching jack-o-lantern shirts every year and I bribe them into taking pictures for me)
It can be a bit daunting knowing where to go and what to do, however. You can’t do it all. Just come to terms with that right now. Remember, the younger the kids, the lower the expectations. Then whatever your expectations are, go ahead and cut them in half. Plan for food and meltdowns and remember that more is NOT better with the younger set. A wagon ride and a pumpkin are all it takes! In a noble attempt to help you out, I’ve rounded up all the local festivals I could find and put the details together for you right here. I hope this will help you choose and plan wisely. If I’ve missed any, please let me know!
One final tip – take the pictures at the beginning of your trip! That way, if it all goes sideways and you have to cut and run early, you have pictures that you can post on Facebook and no one will be the wiser. Then you can store up that experience and try again next weekend. Or next year. Fall comes every year, and as long as you stay here in the best place to live ever, you will always have plenty of festivals to choose from.
Shenandoah Valley Apple Harvest Festival
More of a carnival than a traditional farm festival, this one-weekend-only community event kicks off apple season in the Valley at the Frederick County Fairgrounds. It’s being held September 21-22 this year. There are plenty of apples to go around with an apple pie eating contest, free apples, apple butter made on site, and all kinds of concession vendors, as well as inflatables for the kids, an antique car show, bingo, live entertainment, and a hard cider/beer tasting. This is not the place to go for hay rides, apple picking, or games. However, if you’re looking for crafts, food, and an entertaining place to get out and spend a day outside, you should check it out! Admission is $10 or less for everyone 6 and up – look for $1 off coupons around town.
Marker Miller
Marker Miller, with its pirate ship playground and pick-your-own produce, is a local favorite for playdates and getting out of the house every summer. If you’re looking for low-key, simple fall fun this is the place for you! Their playground and pick-your-own fruit open all week long – check the website for what’s currently available for picking. Weekends in September and October they have a free cow train for the kids and a $2 wagon ride around the farm. They have several festival weekends with special food and live music available. This year the apple harvest festival is October 12-13 and the pumpkin festival is October 26.
Hill High Farm
Just a bit farther down the road from Marker Miller, Hill High is another local favorite- free admission includes a petting zoo, playground, and hay bale maze. Daytime activities – hay rides and a corn maze, $6 each – are Saturdays and Sundays from 10-5 starting Sept. 22 and going through the end of October. The hayride and corn maze are also open Friday, Saturday, and some Thursday evenings from 7-10 to experience in the dark (bring a flashlight!). Their haunted house, $6 as well, is open many afternoons and evenings during the season. Calendars are on the website!
Wayside Farm
If you want to stick close to Winchester, but get the full “fall festival” experience with pig races, a corn maze, a pumpkin drop, and enough activities to keep your kids entertained for a good part of the day, check out Wayside Farm in Berryville. Since it’s close to us, this is the festival we go to every year and my kids look forward to it all year long! They love watching the farmers drop pumpkins from up on a cherry picker, the rubber duck races, and climbing on the hay bales. The you-pick pumpkin patch is a short walk from the festival site – pumpkins are not included in the admission cost, but there are many to choose from. Open Saturdays and Sundays from 10-6, admission is $12/person ages 3 and up (group rates available), but they often have deals available on sites such as Groupon or CertifiKid.
West Oaks Farm
West Oaks is the newest addition to Winchester’s family-friendly agritourism scene, and they are quickly becoming one of our favorites! They have had a small market on Cedar Creek Grade, but recently opened a larger Farm Market out Middle Rd., next to Orchard View Elementary School. They have multiple spaces for indoor and outdoor entertaining, including an outdoor playground and an inside corn bin for the kids, and they sell food on-site. They are offering 2 festivals this fall – an Apple Festival on September 28th and a Fall Festival on October 19th. Both events offer free admission including a bounce house, playground, music and other activities. There will be a charge to do the hay ride or corn maze. Plenty of food and alcohol are available on site, so please don’t pack your own. The Apple Festival will also include a special Iris show – with flowers being shown and sold, ready to go into the ground!
https://www.westoaksfarm-market.com/
Great Country Farms
Another all-day adventure option, but one that is open all week long, is Great Country Farms, located in Bluemont in Loudoun County just a few minutes past the Clarke County line on Rt. 7. Admission includes wagon rides to the current pick-your-own fields and lots of playgrounds and activities. My kids especially love the giant jumping pillow and American Ninja Warrior course! Weekends in September and October have added festival activities – September features apples while October features pumpkins.The $8 child/$10 adult admission price goes up by $2 on the weekend, but military are free and CertifiKid deals are often available. You can easily spend a whole day exploring all of the activities at the farm!
Temple Hall
While you’re headed east to Loudoun, you can keep going and check out Temple Hall just north of Leesburg on Rt. 15. Temple Hall is a county park that is open to the public free of charge during the summer with lots of animals to visit, a playground, and a jumping pillow. On weekends from September 28-Nov 5 it transforms into a fabulous fall festival with pig races, paintball, pumpkin blasters, and a big corn maze! Admission is $15 adults/$12 for kids ages 3-11. The last time we went to this one my boys were only 1 & 2 and they had so much fun! I’m sure they would enjoy it just as much now that they’re bigger.
Joshua's Hands Waterford Fall Festival
Joshua’s Hands is local charity organization run by the Guthrie family in memory of their son Josh. One of their major events each year is a large fall festival at their farm in Waterford (in the Northeastern part of Loudoun County, about 40 min east of Winchester) – this year’s event is on October 5. They have lots of games and activities, food, animals, music, demonstrations, and it’s the only festival I know of that includes a spelling bee! It’s all free of charge, but there is a live auction in the afternoon to support the charity. We’ve never been to this one, but I know several people who have been and they all tell me it’s a really fun day for the family!
http://joshuashands.org/Fall_Festival.html
Leesburg Animal Park
If you’re in the Leesburg area and you have animal lovers, Pumpkin Village at Leesburg Animal Park is a must-visit. A mini-zoo that’s open year-round, from Sept 21-Nov 5 they put on their Pumpkin Village, with special entertainment on the weekends. They even offer pony and camel rides! (additional fee) Admission ranges from $12-$19, depending on when you go, with kids under 2 included for free.
Cox Farms
For the most extensive, jam-packed fall festival around, travel about an hour east of Winchester to Centreville, Va and visit Cox Farms. There is plenty to do for the whole family, from a Kiddie Zone for the littles to bigger slides and swings for the big kids. At night, they put on“Fields of Fear” with a range of really terrifying teenager/adults activities. Check out their website for all of the details, including lots of tips for your visit. Be sure and look at the calendar because admission ranges from $7-$20 depending on when you go for the fall festival during the day, and from $15-$35 for the Fields of Fear at night.
Hartland Farms
About 20 minutes east of Front Royal on Rt. 66, you’ll find Hartland Farms. The fall festival, held on weekends, is highlighted by lots of great food and plenty of fun activities – hay rides, a jumping pillow, pig races, and a corn maze. Admission is $10 for ages 3 and up – they accept debit cards, but not credit cards so be prepared! – there is a separate orchard for picking your own apples on the property. I haven’t been to this one, but have been told from a reliable source that kids love it, especially getting to shoot an apple cannon at an old car!
http://www.hartlandfarmandorchard.com/fall-festival-weekends.html
Richard's Fruit Market
Just south of Winchester in Middletown, Richard’s Fruit Market is a family-owned farm that grows and sells a wide variety of products – from beef to fruits and veggies to bakery items to pick-your-own flowers! Their 2019 Apple Festival is taking place October 19th. They will have plenty of food straight from the farm and beer flights available to purchase. Admission is free, including live music, wine tasting, and activities for the kids such as a petting zoo, hay wagon, barrel train, and lots of space to run.
Orr's Farm Market
Up in Martinsburg, WV, Orr’s Farm Market offers Fall Fun Days with a field full of vendors, food, and bluegrass on Sept 21-22. Admission is free, but tokens are required for some activities such as moon bounce, pumpkin painting, and face painting. Hay rides to their pumpkin patch and corn maze (prices vary from $5-$9) are available both at the festival and during the week. The pumpkin patch, featuring Spookley the Square Pumpkin and his anti-bullying message, is open now through Halloween.
BUMFS Apple Harvest Festival
If you’re looking for something a little bit different from the corn mazes and pumpkin patches, head up to Burlington, WV for the BUMFS Apple Harvest Festival Oct. 5-6. They feature apple butter making, fireworks, a parade, and lots of artisan craft vendors on site. There’s an antique car show, music, and an artisan village where you can watch craftsmen at work.
http://www.bumfs.org/ahf.html
Other pick-your-owns
Just in case that wasn’t enough for you, there are plenty of other local orchards that offer pick-your-own fruits and vegetables! They often feature wagon rides, on-site food, etc, but without all the extra activities and fees. It’s a great outing for smaller kids with shorter attention spans, or for regular visits throughout the summer and fall. Kids love eating food they’ve picked, and will often surprise you by trying new things when they get to see them grown and harvested! A few more options:
Cline’s
https://www.facebook.com/Clines-Farm-282623981813425/
Rinker’s
Mackintosh Fruit Farm
https://www.mackintoshfruitfarm.com
(From the festival list above, Marker-Miller, Hill High, Great Country Farms, and Hartland Farm also have pick-your-own)