20 Things to Do in Charlottesville This Fall (Your Ultimate Bucket List)

Fall is the perfect time to explore Charlottesville's working farms! Treat yourself to a classic fall experience with:

1. Pick Your Own Apples

Apples are just coming into season in September, which means the area is ripe with picking opportunity.

• Carter Mountain Orchard
• Chiles Peach Orchard
• *NEW* Trump Winery

2. Visit the Farmers Markets

Yes, Charlottesville farmers markets are still active and full of local produce, artisan goods, and seasonal treats. There's nothing like perusing farm-fresh finds on a crisp fall morning! We recommend spending a Saturday morning at the walkable Downtown Mall, where you can hit the Farmers Market at IX and the Charlottesville City Market. While you're there, grab brunch and explore the nearby secondhand shops -- all within walking distance! 👉 Find a List of Local Farmers Markets Here.

3. Go to a Fall Festival

Local farms and communities host a variety of harvest-themed events in Autumn, perfect for a weekend of family fun for all ages!

• Fall into Fun Festival | Chiles Peach Orchard | September 20th & 21st
• Harvest Fest | Southwest Mountains Vineyard | September 20th
• Fall Fiber Festival & Montpelier Sheep Dog Trials | James Madison's Montpelier | October 4th & 5th
• Foxfield Fall Races | Sunday, October 5th

this list is being updated as events are added. For the most up-to-date information, visit our Events Page.

4. Find the Perfect Pumpkin

In late September and October, don't miss out on the arrival of pumpkins! The Charlottesville area has a wide variety of gardens, farms, and orchards that have loads of gourds to choose from!

The Monticello Wine Trail, awarded Wine Region of the Year in 2023 by Wine Enthusiast, is home to more than 40 award-winning wineries! Fall, and particularly Virginia Wine Month, is an excellent time to explore, with crisp air, golden foliage, and cooler temperatures that make vineyard visits even more inviting.

5. Follow the Gold Medal Trail

An excellent starting point! The Gold Medal Trail is made up of wineries who won top awards in the Virginia Governor's Cup, the state's premiere wine competition with over 620 of the best Virginia wines, ciders, and meads submitted and sampled. In 2025, 25 producers across the Monticello Wine Trail took home 57 gold medals, with Barboursville Vineyards taking home the Governor's Cup for their 2023 Vermentino.

6. Pair Wine with Gourmet Bites

Savor the season with perfectly paired flavors -- think crisp whites and rich reds with farm-fresh fare and curated bites. To start, venture out to Eastwood Farm and Winery. Located a short drive from Charlottesville, Eastwood is open year-round, seven days a week and they do an excellent job of showcasing seasonal, local ingredients on their menu, including a selection of gorgeous charcuterie board items! 👉 Here are Seven More Award-Winning Wineries with Incredible Food Pairings

7. Uncork a Unique Wine Adventure

What pairs perfectly with wine? A side of adventure! From horseback rides through scenic vineyards to polo matches with panoramic mountain views, there are plenty of exciting experiences on the Monticello Wine Trail that go beyond the glass. 👉 Here are Eight of Our Favorite Experiences

Whether you're a seasoned hiker or just looking for a scenic stroll, fall in Charlottesville and Albemarle is prime time for outdoor adventure.

8. Go For a Hike

Discover scenic, family-friendly trails right in Charlottesville and Albemarle County, perfect for a morning stroll or an afternoon adventure. Ivy Creek Natural Area and the Saunders-Monticello Trail offer well-maintained paths, kid-sized loops, and plenty of wildlife to spot along the way. For those craving mountain views, the Blue Ridge Parkway is just a 30-minute drive and chock full of hiking trails and scenic overlooks that offer sweeping panoramas. 👉 Here's a List of the Best Hiking Trails in Charlottesville

9. Conquer the Loop de 'Ville | Sat. September 27th

Loop de 'Ville is the go-to, free event for beginners and experienced trail-users alike to celebrate the connectedness of community through the Rivanna Trail. This is your chance to experience a guided and supported hike, run, or bike on the ~25-miles of trails that encircle Charlottesville. 👉 Six Reasons to Attend the Loop de 'Ville Festival

10. Tee Off

Fall is the perfect season to hit the greens and admire the stunning mountain backdrops. 👉 5 Courses for the Perfect Golf Getaway in the Charlottesville Area!

11. Chase Fall Colors

While the Blue Ridge Mountains draw a high volume of visitors this time of year, fall foliage transforms the entire region into a tapestry of reds, oranges, and gold, including Charlottesville and Albemarle County. There are plenty of closer (and less crowded) spots to witness the beauty of fall. Lace up your boots and explore:

If you're less into hiking and more into admiring the fall foliage while sipping on a glass of award-winning wine or enjoying some farm-to-table food, we've got you covered too. 👉 Here are Ten Places to Enjoy Fall Colors in Charlottesville

12. Discover Charlottesville's Hidden Gems

Coming into town for a concert, UVA game, or night out on The Corner? Spend some time exploring beyond your usual go-to eateries! 👉Check out these 10 Must-Try Hidden Gem Restaurants, recommended and written by expert foodie Rachel Buccola (cville.foodie)!

13. Go on a Culinary Adventure

Take your taste buds on a memorable journey through Charlottesville’s vibrant food scene. From guided food tours to hands-on experiences, it's all about exploring local flavors and indulging in delicious bites... all while having extra fun along the way! Here's a few recommendations to get you started:

• Go on a guided foraging walk with the Blue Ridge Mycological Society! 9/21 at 2:30PM
• Discover the heart of Charlottesville on a delicious walking food tour with C-Ville Bites -- tours go out on Thursday, Fridays, Saturdays, and Sundays at varying times.
• Pi-Napo Pizzeria offers pizza making classes where participants can make their own authentic Neapolitan pizza from scratch.
  
• Master the art of making pasta from scratch at Pippin Hill Farm & Vineyards! They have two classes scheduled this fall -- October 29th and November 19th.
  
• Enjoy an evening on America's Founding River with the James River Batteau Company! Go on a two-hour sunset cruise, featuring charcuterie and live music, or treat yourself to the full 'Farm to Batteau' experience, featuring an open fire, family-style, farm to table dinner.

14. Enjoy a Meal Outside

Outdoor dining in Charlottesville is at peak enjoyment during the fall season. Whether you’re interested in a quiet morning coffee alfresco, a lively dinner, or boozy brunch – there’s an option for everyone! Start your adventure on the historic pedestrian Downtown Mall, where you’ll find more patio seating per capita than anywhere else in Charlottesville—perfect for sipping, snacking, and people-watching. Just a short stroll away, IX Art Park offers even more outdoor dining options, along with the added bonus of interactive art installations to explore before or after you savor your meal. A few blocks south and east, the Belmont neighborhood has a lively patio scene worth exploring. Exploring west of town? Crozet has several restaurants with outdoor seating that feature beautiful mountain views. 👇Get Started with Our Map of Recommendations

15. Go to a Concert on the Downtown Mall

The Downtown Mall comes alive with music in the fall, with an incredible lineup of performances at a range of venues -- each with their own appeal and personality! From big-name acts to local favorites, here are just a few can't miss concerts coming up:

16. Pair Your Meal with Live Music

Pair your dining experience with a side of music! Many Charlottesville restaurants host live musicians on the weekend (and some on the weekdays), creating the perfect setting for a relaxed dinner, lively night out, or weekend brunch. Local hotspots include: The Bebedero, The Whiskey Jar, Miller's Downtown, and Holly's Diner. 👉 Visit our Concerts & Live Music Page for Info on Upcoming Events

17. Enjoy Vineyard Vibes

Sip local wines while enjoying live entertainment at one of the area's many scenic vineyards or cideries. The blend of music, mountain views, and crisp fall air creates the perfect laid-back afternoon or evening. These venues are a good place to start, but we recommend checking their websites for more detail 👇:

• Keswick Vineyards
• Albemarle Ciderworks
• Fallen Tree Vineyard and Farm
• Eastwood Farm and Winery

18. Catch a Screening at the Virginia Film Festival | October 22nd-26th

The Virginia Film Festival, now in its 38th year, is widely recognized as one of the leading regional film festivals in America. The festival typically screens 100+ films throughout various venues in Charlottesville, with panels featuring actors/producers, dynamic conversations, and special events sprinkled throughout.

19. Support Local Artisans

Have you ever wondered how iron is forged, a clay pot is thrown, or what it really takes to make jewelry? Head to Charlottesville on November 8th and 9th for the area's annual Artisans Studio Tour, where you can see talented artisans in action in their very own maker spaces! The Crozet Fall Arts and Crafts Festival on October 11th and 12th is also an incredible opportunity to peruse artisan vendors, with over 120 vendors exhibiting.

20. See What's New at the Fralin Museum

Check out the Fralin Museum of Art’s newest free exhibits! These fresh installations offer a unique glimpse into diverse cultures and creative perspectives—making this a must-visit for art lovers this fall. 👉 Learn More About the Fralin's New Exhibits