Updated for 2025 Fall Events on August 30, 2025.
Hey there, fellow autumn enthusiasts! 🍂 If you’re anything like me, fall is your favorite season. The crisp air, the pumpkin candle scents, and the leaves turning into a kaleidoscope of colors—what’s not to love? And if you happen to find yourself in Charlottesville, Virginia this fall, boy, are you in for a treat. Whether you’re a local or just visiting, I’ve got the lowdown on some seriously fun Charlottesville Fall Activities & Family Events that will make you fall (pun intended) in love with this charming town.
Table of Contents
Visit a Pumpkin Patch
Chiles Peach Orchard
What’s fall without pumpkins? Head over to Chiles Peach Orchard & Farm Market where they transform into a pumpkin paradise every autumn. Pick out your perfect pumpkin for carving (or just for Instagram pics—I won’t judge). Situated in Crozet, about 20 minutes from Charlottesville the views are just gorgeous! You can pick pumpkins from late Sept through November
But it’s not just about the pumpkins. The orchard offers hayrides, a corn maze, and even apple picking if you want to double down on your Charlottesville fall activity fun. Plus, there’s a farm market where you can grab some fresh cider and homemade goodies. Trust me, their apple cider donuts are to die for! 🍩
Chiles is the only local place I found where the pumpkins aren’t pre-picked.
- Address: 1351 Greenwood Road, Crozet, VA 22932
- Website: chilesfamilyorchards.com
Go Apple Picking
Carter Mountain Orchard
Picture this: You’re surrounded by apple trees as far as the eye can see, each branch heavy with juicy apples just waiting to be picked. 🍏🍎 You grab a basket and start filling it up while taking in panoramic views of the Blue Ridge Mountains. It’s like something out of a Hallmark movie.
But wait, there’s more! Carter Mountain isn’t just about apples. They’ve got fresh cider donuts that are basically little rings of heaven. Trust me; you’ll want to grab a dozen… or two.
Be sure to get a ticket if you plan to go on a weekend and be prepared for crowds because this is a fav on most lists of Charlottesville family events!
- Address: 1435 Carters Mountain Trail, Charlottesville, VA 22902
- Website: cartermountainorchard.com
Fruit Hill Orchard
If you are looking for less crowds and a shorter walk you might find Fruit Hill is a better fit! This family owned and operated orchard located 30 min southeast of Cville is full of charm without the masses of people. Imagine this: crisp air, golden leaves crunching underfoot, and trees laden with juicy apples just waiting to be plucked. Seriously, it’s like something out of a cozy fall movie.
Be prepared to spend some money in the farm store because there is just so much that they offer including various seasonal fruits like peaches and pumpkins in addition to apples and baked goods. I’m literally eating one of their caramel apple cookies while I write this! We’ve already picked some apples this year for my kiddos field trip! Here are a few selfies from the 3 different field trips I did in one day to the orchard 😂.
Fruit Hill Orchard
- Address: 2318 Fruit Hill Lane, Palmyra, VA 22963
- Website: fruithillorchard.com
Hike the Appalachian Trails
Feeling adventurous? Take a hike—literally! Shenandoah National Park is just a short drive away and offers some of the most breathtaking trails you’ll ever set foot on. Whether you’re a seasoned hiker or someone who considers walking to the mailbox exercise, there’s something here for everyone.
Trust me, there’s nothing quite like standing on a mountain overlook, feeling like you’re on top of the world, and thinking, Yep, this beats Netflix. So grab your water bottle, maybe a snack (or three), and hit the trails—you won’t regret it!
Here are 3 popular trails to get started with!
Humpback Rocks
- Address: Humpback Gap Parking Area, Blue Ridge Parkway Milepost 6, Afton, VA 22920
- Website: nps.gov
- Description: Humpback Rocks is a popular hike with stunning views, about 30 minutes from Charlottesville. The trail is steep but relatively short, making it a favorite for catching sunrise or sunset.
Riprap Trail
- Address: Riprap Parking Area, Skyline Drive Milepost 90, Shenandoah National Park, Crozet, VA 22932
- Website: nps.gov
- Description: Located in Shenandoah National Park, Riprap Trail is a loop that combines with the Appalachian Trail for part of the hike. It features stunning overlooks, a waterfall, and a swimming hole. Entry to the park requires a fee.
Rockfish Gap
- Address: Rockfish Gap Parking Area, Intersection of Skyline Drive and Blue Ridge Parkway, Afton, VA 22920
- Website: visitcharlottesville.org
- This is a convenient access point to the Appalachian Trail right where Skyline Drive meets the Blue Ridge Parkway. It’s a great starting point for both short hikes and longer treks on the trail.
Enjoy a Scenic Fall Drive
If hiking isn’t really your thing but you still want those epic views I mentioned earlier (I mean who wouldn’t?), then hop in your car and take a drive down Skyline Drive 🚗🍁🏞️.
This 105-mile road runs through Shenandoah National Park and offers stunning vistas at almost every turn-out point along the way—perfect for leaf peeping without breaking too much sweat!
Rockfish Gap Entrance to Skyline Drive:
- Rockfish Gap Entrance Station
- Address: Intersection of U.S. Route 250 and Skyline Drive, Afton, VA 22920
This entrance is about a 30-minute drive west of Charlottesville and is the southernmost entrance to Shenandoah National Park, providing access to Skyline Drive.
Attend a Fall Festival or Fair
If festivals are more your speed, Charlottesville has plenty to offer during fall. From pumpkin patches to craft fairs and everything in between, there’s always something happening around town. From arts and crafts to film to horse racing and of course harvest celebrations there is always something going on! A few of the most popular are listed below:
Virginia Film Festival
- Dates: October 22-26, 2025
- Location: Various venues throughout Charlottesville
- Description: The 38th annual Virginia Film Festival is a program of the University of Virginia, showcasing diverse films including premieres, documentaries, and shorts with panels and Q&A sessions.
- Website: virginiafilmfestival.org
Crozet Arts and Crafts Festival
- Dates: October 11-12, 2025
- Location: Claudius Crozet Park, Crozet, VA
- Description: This popular arts and crafts festival features 120+ artists and artisans from across the country, offering handmade items such as jewelry, pottery, and paintings. The festival also includes live music, food vendors, and family-friendly activities.
- Website: crozetfestival.com
Montpelier Hunt Races
- Date: November 1, 2025
- Location: James Madison’s Montpelier, Montpelier Station, VA
- Description: A tradition since 1934, the Montpelier Hunt Races feature steeplechase races, tailgating, and family activities on the grounds of James Madison’s historic home. This event is a great way to experience Virginia’s horse racing culture and beautiful fall scenery.
- Website: montpelierraces.org
Fall Foliage Festival Art Show
- Dates: October 11-12, 2025
- Location: Downtown Waynesboro, VA
- Description: Held in nearby Waynesboro, this festival features fine arts and crafts from over 150 artists, live music, and food vendors. It’s a great opportunity to explore local and regional talent while enjoying the fall colors.
- Website: svacart.com
Apple Harvest Celebration at Carter Mountain Orchard
- Dates: Weekends throughout October 2025
- Location: Carter Mountain Orchard, Charlottesville, VA
- Description: Celebrate the apple harvest with fresh apple picking, hayrides, live music, and family-friendly activities. Enjoy delicious treats like apple cider donuts, caramel apples, and fresh cider.
- Website: cartermountainorchard.com
Enjoy the Crisp Fall Air at a local Winery, Brewery or Cidery
There is no shortage of places to go around Charlottesville to enjoy some adult beverages 🍻. Add to that the stunning views of the mountains and the crisp fall air, where else would you rather be!!!
Wineries
- King Family Vineyards
- Event: Sunday Polo Matches
- Dates: Every Sunday until October 26, 2025
- Description: Enjoy free polo matches on the beautiful grounds of King Family Vineyards. Bring a picnic and enjoy wine by the glass or bottle. This is a family-friendly event, perfect for a relaxing afternoon. Matches begin at 12:00pm, and gates open at 10:00am.
- Website: kingfamilyvineyards.com
- Veritas Vineyard & Winery
- Description: Veritas is known for having “stunning views of the Blue Ridge Mountains” and offers both indoor and outdoor dining experiences. The winery regularly hosts educational events and seasonal celebrations beyond their signature summer concert series.
- Website: veritaswines.com
- Pippin Hill Farm & Vineyards
- Description: Pippin Hill is a unique “culinary vineyard” in North Garden, Virginia, that combines award-winning winemaking with an exceptional farm-to-table dining experience. They describe themselves as offering “wine and food grown here; enjoyed here” with a focus on garden-to-table cuisine.
- Website: pippinhillfarm.com
Cideries
- Bold Rock Hard Cider
- Event: Fall Harvest Festival
- Date: TBD
- Description: This family-friendly event features live music, food trucks, cider tastings, and activities for kids. Celebrate the harvest season with local craft cider.
- Website: boldrock.com
- Castle Hill Cider
- Event: CiderFest
- Date: TBD
- Description: A day filled with live music, cider tastings, and local food vendors. Enjoy the scenic views of the orchard and take a tour to learn about the cider-making process.
- Website: castlehillcider.com
Breweries
- Devils Backbone Brewing Company
- Event: Oktoberfest
- Dates: TBD
- Description: Celebrate Oktoberfest with live music, traditional German food, and a variety of seasonal beers, including special Oktoberfest releases. Enjoy games and activities for all ages.
- Website: dbbrewingcompany.com
- Blue Mountain Brewery
- Event: Hop Harvest Festival
- Date: TBD
- Description: Join the celebration of the hop harvest with fresh hop beers, live music, and food. This event highlights local ingredients and the brewery’s commitment to farm-to-glass brewing.
- Website: bluemountainbrewery.com
- Three Notch’d Brewing Company
- Event: Pumpkin Smash Bash
- Date: TBD
- Description: Enjoy a variety of pumpkin beers, including Three Notch’d’s seasonal favorites. The event features live music, food, and the smashing of pumpkins for all to enjoy.
- Website: threenotchdbrewing.com
These events provide a great way to experience the vibrant local craft beverage scene while enjoying the beautiful fall weather in the Charlottesville area. Be sure to check each venue’s website for the most up-to-date information and event details.
2024 Charlottesville Fall Activities & Family Events
So there you have it—my ultimate guide to making the most outta fall in Charlottesville! Whether you’re picking apples or exploring historical sites; hiking mountains or sipping local brews; immersing yourself in art or catching some flicks—you’re bound to have an unforgettable experience. Plus most of these places have gorgeous backdrops for family or maternity photos so check out our portfolio and book a session!
VIP List Benefits:
- First access to fall portrait dates
- Head start before general booking opens
- Priority consideration for premium time slots
- Weather flexibility with backup date options
Remember folks: life’s too short not to chase after those golden leaves and savor every moment (and donut) along the way!
Now go out there & make this season one for books! 🍂✨
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Melissa Arlena is an award winning lifestyle newborn photographer in Charlottesville and Richmond, Virginia who has earned her Master Photographer Certification from NAPCP in maternity, newborn and family photography. Her natural and simple work has been featured in magazines and online blogs worldwide. She has been named Best Maternity and Newborn Photographer in Richmond and Charlottesville, VA in 2024.
