What’s Happening This Weekend in Charlottesville
Friday, September 4, 2026
- Ice Cream Social at Cake Bloom
- Storytime with Hannah at Bluebird & Co.
- Shenandoah County Fair in Woodstock, VA
- Botanical Arts Festival at Botanical Garden of the Piedmont
- Free roller skating at Carver Rec Center
- Virginia Oysters & Wine with Live Music at Eastwood Winery
- Fridays After Five at the Ting Pavilion
Saturday, September 5, 2026
- Shenandoah County Fair in Woodstock, VA
- Botanical Arts Festival at Botanical Garden of the Piedmont
- All Ages Storytime at New Dominion Bookshop
- Into the Forest: A Musical Nature Experience at the Crozet Library
- Live music at Chiles Peach Orchard
- Live music at Keswick Vineyards
- Free roller skating at the Greenwood Community Center
Sunday, September 6, 2026
- Botanical Arts Festival at Botanical Garden of the Piedmont
- Pokémon League & Learn to Play at The End Games
- Free roller skating at Carver Rec Center
- Live music at Keswick Vineyards
- Live music at Chiles Peach Orchard
- Labor Day Celebration at the Boar’s Head Resort
Looking for family fun in the Charlottesville area? There are plenty of September events in Charlottesville and Albemarle County to add to your calendar.
Whether you want need an idea for date night, don’t want to miss your favorite fall festival, or are just trying to find out what’s happening this weekend in Charlottesville, we’ve got you covered.
Jump to September Events in Charlottesville
For more ideas, don’t forget to bookmark the CharlottesvilleFamily calendar, which is updated every week with events in Charlottesville, Albemarle, Richmond, and the Shenandoah Valley.
September Festivals & Fairs in Charlottesville
Shenandoah County Fair
Where: Shenandoah County Fairgrounds (Woodstock)
When: Aug. 25–Sept. 5 • times vary
Botanical Arts Festival
Where: Botanical Garden of the Piedmont (Charlottesville)
When: Sept. 1–Sept. 30, 2026 • times vary
Labor Day Celebration
Where: Boar’s Head Resort (Charlottesville)
When: Sept. 6, 2026 • 4:00 pm – 9:00 pm
Mini Petting Zoo
Where: Keswick Vineyards (Keswick)
When: Sept. 7, 2026 • 8:00 am – 5:00 pm
Charlottesville Chamber Music Festival
Where: Various locations
When: Sept. 8–19, 2026 • various times
Cville Veg Fest
Where: Ix Art Park (Charlottesville)
When: Sept. 13, 2026 • 11:00 am – 4:00 pm
Youth Film Festival
Where: The Paramount (Charlottesville)
When: Sept. 13, 2026 • 5:30 pm – 8:00 pm
Central Virginia is full of family-friendly adventures this time of year! Find pumpkin patches, hayrides, corn mazes, live music, farm activities, and more at our favorite local fall festivals.
Cville Sabroso
Where: Washington Park
When: Sept. 19, 2026
State Fair of Virginia
Where: Meadow Event Park (Doswell)
When: Sept. 25–Oct. 4, 2026
Local Charlottesville Storytimes
Storytime at the Garden
Where: Botanical Garden of the Piedmont (Charlottesville)
When: Sept. 9, 2026 • 10:00 am – 10:45 am
Storytime with Hannah
Where: Bluebird & Co. (Crozet)
When: Fridays • 11:30 am – 12:00 pm
All Ages Storytime
Where: New Dominion Bookshop (Charlottesville)
When: Saturdays • 11:00 am – 12:00 pm
Creation Station Storytime
Where: Virginia Discovery Museum (Charlottesville)
When: Mondays • 10:30 am – 11:00 am
September Date Ideas in Charlottesville
Fridays After Five
Where: Ting Pavilion (Charlottesville)
When: Sept. 4 & 11 • 5:30 pm
Ice Cream (& Cake!) Social
Where: Cake Bloom (Charlottesville)
When: Fridays • 3:00 pm – 6:00 pm
Virginia Oysters & Wine with Live Music
Where: Eastwood Winery (Charlottesville)
When: Fridays • 5:00–8:00 pm
Live Music Weekends
Where: Chiles Peach Orchard (Crozet)
When: Saturdays & Sundays • 1:00–4:00 pm
Author Talk w/ Mengxi Seeley
Where: Northside Library (Charlottesville)
When: Sept. 15, 2026 • 7:00–8:00 pm
Chamber Music Festival Free Concert
Where: The Paramount (Charlottesville)
When: Sept. 18, 2026 • 12:30 pm
Learn more.
Music Trivia Night
Where: Crozet Library (Crozet)
When: Sept. 23, 2026 • 7:00 – 8:30 pm
Outdoor September Events in Charlottesville
Little Nature Explorers
Where: Botanical Garden of the Piedmont (Charlottesville)
When: Tuesdays • 10:00 am – 11:15 am
Into the Forest: A Musical Nature Experience
Where: Crozet Library (Crozet)
When: Sept. 5, 2026 • 11:00 am – 12:00 pm
Central Virginia Star Party
Where: Albemarle CiderWorks (North Garden)
When: Sept. 12, 2026 • 6:30 pm – 10:00 pm
Little Naturalists
Where: Ivy Creek Natural Area (Charlottesville)
When: Sept. 14, 2026 • 10:00 am – 11:30 am
Free Entrance Day
Where: Shenandoah National Park
When: Sept. 17, 2026 • all day
Find the best kid-friendly hikes in Central Virginia, plus hiking adventures that are pet-friendly! And don’t forget to read our tips for preventing tick bites when you’re exploring outdoors.
Goat Walk & Sanctuary Tour
Where: Sentient Sanctuary (Scottsville)
When: Sept. 19, 2026 • all day
Fall Into Fun
Where: Chiles Peach Orchard
When: Sept. 19–20, 2026 • 9:00 am – 6:00 pm
Fourth Friday Solar Viewing
Where: Ivy Creek Natural Area (Charlottesville)
When: Sept. 25, 2026 • 12:00 pm – 1:00 pm
Loop de Ville
Where: Rivanna River Co. (Charlottesville)
When: Sept. 27, 2026 • 8:00 am – 5:30 pm
Creative Events in Charlottesville
Free Community Day
Where: The Looking Glass at Ix (Charlottesville)
When: Sept. 3, 2026 • 12:00–5:00 pm
Curiosity Club with REAL Lab
Where: Northside Library (Charlottesville)
When: Sept. 3, 2026 • 4:00–5:00 pm
Toddler Movement & Yoga
Where: Virginia Discovery Museum (Charlottesville)
When: Wednesdays • 10:30–11:00 am
Tiny Tiers Mini Cake Decorating Workshop
Where: Cake Bloom (Charlottesville)
When: Wednesdays • sessions start at 1:00 pm
Declaration of Independence Print Shop
Where: Monticello (Charlottesville)
When: Sept. 10, 2026 • 11:00 am–2:00 pm
DIY-U Kids’ Workshops
Where: Lowe’s (Charlottesville)
When: Sept. 19, 2026 • 10:00 am–1:00 pm
Find many more free creative events, plus book clubs and storytimes for all ages, in the Jefferson-Madison Regional Library calendar.
Family Studio Day
Where: Second Street Gallery (Charlottesville)
When: Sept. 19, 2026 • 10:00 am–2:00 pm
Charlottesville September Events for Teens & Tweens
Pokémon League & Learn to Play
Where: The End Games
When: Sundays • 1:00–4:00 pm
Free Roller Skating
Where: Carver Recreation Center
When: Wednesdays, 5:00 pm • Fridays 4:00 pm • Sundays, 12:00 pm & 3:00 pm
School’s Out Hangout
Where: Central Library (Charlottesville)
When: Sept. 8 & 18, 2026 • all day
Aspiring Author Workshop
Where: Northside Library (Charlottesville)
When: Sept. 12, 2026 • 2:00 pm
Club Air
Where: Get Air Charlottesville
When: Fridays & Saturdays • 7:00–10:00 pm
Roller Skating Night
Where: Greenwood Community Center, Crozet
When: Saturdays • 6:00–8:00 pm
Teen Dungeons & Dragons Club
Where: Gordon Ave. Library (Charlottesville)
When: Sept. 14, 2026 • 5:00–7:00 pm
FAQs About September Events in Charlottesville
Are there free events for families happening in Charlottesville in September?
There are many festivals with free entry happening around Charlottesville in September, including Cville Veg Fest at Ix Art Park on September 13th, weekly storytimes at bookstores and libraries, Fridays After Five at the Ting Pavilion through September 11th, and free weekly roller skating at Carver Rec Center in Charlottesville and Greenwood Community Center in Crozet.
The Botanical Arts Festival, which happens at various locations around town the first week of September, has many free events and exhibits. Shenandoah National Park has free entry all day on September 17th, and The Looking Glass at Ix Art Park hosts free community hours the first Thursday of every month. There are also free art days, lego building, book clubs, and more at JMRL library branches every week.
Where can I hear live music near Charlottesville in September?
Fridays After Five at the Ting Pavilion has free live music the evenings of September 4th and 11th. Many wineries near Charlottesville have live music on the weekends in September, including Friday evenings at Eastwood Winery and Saturday and Sunday afternoons at Keswick Vineyards. Both these vineyards are family-friendly and have food and drink options for kids.
Chiles Peach Orchard also host live music in September on Saturday and Sunday afternoons. And the Charlottesville Chamber Music Festival has a free community performance at the Paramount on Friday, September 18th (registration required).
What can teens and tweens do in Charlottesville in September?
Charlottesville libraries host many events for teens and tweens, including craft events, writing workshops, book clubs, and Dungeons & Dragons games. JMRL’s Central location also hosts School’s Out days on September 8th and 18th, when teens and tweens can hang out in the library’s teen space to read, craft, and do school work.
The End Games hosts regular events, including both learn-to-play tutorials and more advanced leagues. Get Air trampoline park has late hours on Friday nights, known as Club Air, for teens to hang out and jump with friends, and Carver Rec Center has free basketball and roller skating hours each week.
Where can I find pumpkin picking in Central Virginia?
Favorite pumpkin patches near Charlottesville include Carter Mountain Orchard, Chiles Peach Orchard, Sarah’s Pumpkin Patch, and Round Hill Farm. We’ve rounded up all our favorite pumpkin picking locations in Central Virginia in one handy guide.
What are good spots for apple picking near Charlottesville?
Charlottesville has many orchards for fall apple picking, include Carter Mountain Orchard, Critzer Family Farm, Chiles Peach Orchard, Henley’s Orchard, and Drumheller’s Orchard. Find all our favorite apple picking spots near Charlottesville, including some that are perfect for scenic day trips.
Charlottesville is full of seasonal fun for families! Find our favorite spots for corn mazes and apple picking. Or, meet up with friends at the best local parks and playgrounds.
For fresh ideas all year long, sign up for our free CharlottesvilleFamily newsletter. And be sure to learn more about our valued partners who serve local families.
CharlottesvilleFamily Editors are locals who care deeply about family and community. We are almost all parents who serve alongside our readers. We’re in the PTO and band boosters, coach sports teams, help with the school fun fair, and more. Our insider perspective, combined with great research and expert input from our wonderful CharlottesvilleFamily Advisory Panel, helps us to provide you with trustworthy advice as you raise the next generation of brilliant and compassionate kids.