Life in Charlottesville is always defined by open-air diversions, but come fall, the possibilities for getting outdoors are as varied and vibrant as the season’s tapestry itself. Looking to pack a festive picnic or leaf peep while getting a workout in? The region’s many parks and trails mean it’s effortless to find your signature autumn escape. Interested in taking a DIY approach to apple and pumpkin picking for the whole family to embrace? We’ve got you covered. And if you’re craving a chance to sip your way through the local wine and cider scene, you’ve come to the right place. Whether your fall bucket list is already brimming with harvest adventures or you’re not sure where to start, here’s your official guide to making the most of autumn in and around Charlottesville this year.
Parks & Trails:
Riverside Park (27 acres): This riverfront escape shines brightest in autumn, with fiery foliage framing its quintessential playground, picnic spots, and wide-open lawns. Meanwhile, the adjacent biking and walking trail makes it easy to soak in crisp air and golden views along the water.
Saunders-Monticello Trail (Easy | 5 mins from downtown): This smooth 4.3-mile out-and-back winds up Carter Mountain to Jefferson’s Monticello. Stroller-and wheelchair-friendly, the route features boardwalks, a pond, and a forest canopy bursting with fall color — ideal for families, bikers, and casual walkers alike.
Rivanna Trail (Easy | circles Charlottesville): This 20-mile loop wraps the city in woodlands, wetlands, and river views. No sweeping overlooks here — just an up-close, colorful collage of leaves underfoot and vivid trees overhead. Accessible from multiple points downtown, it’s a local favorite for year-round walks — and fall is no exception.
Blackrock Summit (Easy 1.6-mile loop | ~1 hour from downtown): Here’s a quick, family-friendly hike with a huge payoff: panoramic views of Shenandoah Valley from a rocky ridge. Follow the Appalachian Trail to the summit, then loop around boulders for vistas in every direction — or tack on the Blackrock Spur for an extra dose of adventure.
Humpback Rocks (Moderate 4.3-mile loop | ~30 mins from downtown): A Charlottesville classic. Choose a steep 1-mile, 700-foot climb or a gentler 4.3-mile loop route — either way, you’ll discover jagged cliffs with jaw-dropping views of the Shenandoah. Bonus: explore the Outdoor Farm Museum nearby, where settlers once used the rock as a landmark that guided wagon trains.
Apple & Pumpkin Picking:
Carter Mountain Orchard: Just minutes from downtown Charlottesville and Monticello, Carter Mountain Orchard pairs sweeping valley views with picturesque fall foliage. What are you waiting for? Grab a basket and step into apple picking, cider sipping, and crisp autumn air.
Henley’s Orchard: A family-run farm since 1932, Henley’s is known for its low-spray apples boasting more than 25 varieties, including the beloved Albemarle Pippin. As summer fruits fade, fall brings crisp apples, pumpkins, and the chance to wander the orchard under eye-catching leaves. Seasonal fun like hayrides and community events add to the orchard’s charm, making it a beloved local spot to celebrate autumn.
The Market at Grelen: Set on 1,000 scenic acres, The Market at Grelen offers pick-your-own apples each fall alongside a charming café, garden shop, and seasonal workshops. Visitors can also wander vivid trails and enjoy a café lunch — best enjoyed with a glass of local wine.
Dickie Brothers Orchard: Granted by King George more than 268 years ago, the Dickie Brothers Orchard has stayed in the same family for generations. Today, visitors come for its many apple varieties and often pair the trip with a hike at nearby Crabtree Falls or an outing to the George Washington National Forest and Wintergreen Resort.
Chiles Peach Orchard: For the ultimate “pick your own pumpkin” experience, head to Chiles Peach Orchard just outside charming Crozet. Framed by stunning mountain views, the orchard overflows with pumpkins, apples, gourds, and squash in every shape and hue. Weekends require tickets for pumpkin picking (kids 12 and under are free), but even without one, you can always stop by the onsite Farm Market, Bakery, or Ice Cream & Wine Shop.
Liberty Mills Farm: Liberty Mills isn’t just famous for having Virginia’s Largest Corn Maze — the farm is known for its pumpkins, too! Just a scenic 30-minute drive northeast of Charlottesville, this autumn playground offers stunning Blue Ridge views and sprawling countryside. Don’t expect a quick stop: tackle the most challenging path through the 25-acre maze, and it could take 2–3 hours to escape — but an 8-acre patch of pumpkins at the end makes the trek well worth your time.
Vineyards & Cideries:
King Family Vineyards: Virginia’s greater wine country may be full of stories, but a visit to King Family Vineyards is a chance to step into one of the state’s most celebrated chapters. Beyond its award-winning wines, the vineyard’s charm lies in its deep roots and the storied sense of history you feel while wandering the grounds. Once summer has faded out of view, visitors can expect a timeless vineyard experience that’s only enriched by the flavors and vistas the fall season brings.
Potter’s Craft Cider: Potter’s Craft Cider celebrates the flavors of autumn with farmhouse-style hard ciders that are equal parts dry, crisp, and refreshing. Just south of Charlottesville off Route 29, the tasting room serves up craft cider, wine, and non-alcoholic options — along with snacks, food trucks, live music, and generous outdoor spaces shaded by the season’s turning trees.
Pippin Hill Farm & Vineyards: Nestled in the foothills of the Blue Ridge Mountains, Pippin Hill Farm & Vineyards comes alive in autumn. Crisp air and colorful foliage spotlight sweeping vineyard views — the idyllic backdrop for sipping estate wines, enjoying seasonal dishes, and joining in festive fall events. From cozy gatherings to memorable moments with friends and family, fall at Pippin Hill embodies Virginia wine country at its most vibrant.
Albemarle CiderWorks: Opened in 2009, Albemarle CiderWorks crafts distinctive ciders from Virginia apples, including favorites like Jupiter’s Legacy, Ragged Mountain, and Royal Pippin that each showcase the best flavors of fall. While there, be sure to stop by the North Garden tasting room for a seasonal sampling, workshop, event, or simply to savor the refreshing taste of locally crafted cider.
Community Events:
Endless View Farms Fall Festival Opening | Sept 20–21, 10 AM–6 PM: Celebrate autumn at this weekend festival with cozy fall vibes, over 25 farm activities, and seasonal treats. Pick your own pumpkins, enjoy games for all ages, and soak in the sights, smells, and flavors of the season. Can’t make it to the annual launch? No problem — the festival runs through November 2nd!
The Crozet Arts & Crafts Festival | October 11-12: The Crozet Arts & Crafts Festival returns for its fall weekend on October 11–12, one of two annual events that draw families from across Central Virginia. At Claudius Crozet Park, more than 120 juried artisans showcase their work alongside food trucks, live music, and hands-on activities for kids and adults. Leashed pets are welcome, making it the ultimate autumn outing for everyone.
SPCA Fall Fest 2025 | October 18th 11AM: Join the Charlottesville-Albemarle SPCA for Fall Fest on Saturday, October 18 — a day of Halloween fun, family activities, and furry friends! Get ready for pumpkin patches, dog costume contests, and more, all while supporting lifesaving care for animals in need.
Apple Butter Makin' Festival | October 4th & 18th: Celebrate autumn at the Orchards of Silver Creek & Seamans, home to the Apple Butter Makin’ Festival that’s complete with mountain-grown apples, crisp cider, and the star of the show: homemade apple butter. Think fall fun from start to finish — crafters, live music (12–3 PM), a winding corn maze, pick-your-own pumpkins, face painting, clowns, and plenty of food vendors. Festivities run from 10 AM to 4:30 PM: the perfect window for a full autumn adventure!
Fall in Focus: Autumn is the quintessential season in Charlottesville — and as this roundup shows, there’s no shortage of fall-focused fun for everyone to enjoy. Our advice? Make sure you map out your adventures for the months ahead so you can pack in as much excitement as possible before the last leaf falls!
Seeking more fall insights? Deciding whether to buy or sell this season? Let’s set up a time to talk and come up with a gameplan tailored to your unique goals.