LABOR DAY WEEKEND
UVA
FESTIVALS
MUSIC
OUTDOORS
FOOD

1. Kick Off the Month: Labor Day Weekend

If you’re visiting for Labor Day, you’ll find plenty of fun ways to start your September in style. Make sure to visit our Events Calendar for the full slate of events happening in the area -- here are a few of our favorites:

2. UVA Shops, Historic Stops, and Sports

Explore, Eat, and Shop Like a Hoo

There's always time to walk around UVA's Grounds, a designated UNESCO World Heritage Site! There are number of guided and self-guided tours available, including those for prospective students. Be sure to use this interactive map to discover lesser-known facts, historic objects, and places across Grounds.

While you're here, you may as well act the part by supporting UVA-staples such as:

Make sure to grab some official UVA gear at the University Bookstore or local boutiques like Mincer's, a family-run shop that's been outfitting Hoos for decades. While you're there, swing around the corner and check out Ragged Mountain Running and Walking Shop, a staple of the local community for 40 years!

UVA Football is Back!

Game day in Charlottesville is an unmatched experience for locals and visitors alike! There are three UVA Football matches in September at Scotts Stadium:

These games are designated Fan First Games, which means UVA is offering tickets at a reduced price. Don't forget to join the pregame excitement by tailgating -- popular parking lot spots are near: Scott Stadium, Fontaine Research Park, and John Paul Jones Arena. UVA has also teamed up with REVELx to offer exclusive travel packages for those that want to travel in and make a weekend of it, including a full-service tailgating experience.

There are plenty of other UVA teams to catch live...

Virginia volleyball coach Shannon Wells recently announced that the women's volleyball program will return to John Paul Jones Arena for five matches during the 2025 season, which includes their matches on September 27th and 28th.

“Playing five matches in John Paul Jones Arena this season is a milestone for Virginia Volleyball, the most we’ve ever had in one season in this amazing venue. JPJ’s energy is electric and every match there feels like something bigger than the game...”

Shannon Wells

3. September Festivals and Special Events

September is one of the most buzzing months in Charlottesville, with festivals happening nearly every weekend. From celebrations of identity to outdoor adventures, here's what we have going on.

Events

Charlottesville and Albemarle County host a variety of visitor-friendly events throughout the year, bringing people together to celebrate food, drinks, music, art, culture, history, the outdoors and more.

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Pippin Hill Farm & Vineyards Cooking Class
Credit: Sera Petras Photography

4. Live Music All Month Long

Historic Downtown Mall

A popular choice for date night thanks to the numerous parking options nearby, overall walkability, and proximity to dining, drinking, and shopping options. The Southern Cafe & Music Hall, Jefferson Theater, and Paramount Theater all have a number of incredible performances scheduled for September! Make a night of it or stick around grab a bite in the morning! 👉 Take a look at some of our favorite brunch spots

Wineries & Cideries with a View

Head over to Keswick Vineyards for Wine Down Wednesdays, featuring live music, signature sandwiches from Barrel & Board, and award-winning wine! They also usually have live music on Saturday nights. 👉 Check their website for more information

Chisholm Vineyards' Sunset Soiree Series hosted every Friday night from 6-9PM, features live music, a rotating slate of food trucks, and beautiful sunset views of the Blue Ridge Mountains. 👉 See the full list of upcoming bands and food trucks

Head over to Albemarle Ciderworks on Saturdays from 2:30-4:30PM for Live Music in the Orchard, featuring hard cider, local musicians, and light bites -- outside food is welcome!

Karaoke & Open Mic Nights

There's no shortage of karaoke or open mic nights in town! Head over to our live music calendar to find the night/venue that works best for you.

5. Outdoor Experiences, Adventure, and Recreation

Pick-Your-Own Fields

Late summer peaches linger into early September, but apple picking season will be in full-swing by mid-September and reservations are required for weekend picking from mid-September-November at Carter Mountain. Plus, their Thursday Evening Sunset Series will be in full swing offering arguably the BEST sunset view of Charlottesville. 👉Use this handy chart to see when different apple varieties are in season

Chiles Peach Orchard also has apples available for picking in September along with some late season peaches, flowers, and potentially pumpkins at the end of the month. 👉 Check their fruit availability chart to see what's available

*NEW* in 2025, Trump Winery will be hosting a pick-your-own orchard experience (expected to begin the second week of September). Reservations can be made online. Plan ahead -- Trump Winery is hosting their Inaugural Apple Harvest Festival in October.

Polo Matches at King Family Vineyards

Polo in September at King Family Vineyards is a family-friendly experience you won't want to miss. Matches begin at 12PM every Sunday (weather permitting). Be sure to bring chairs, blankets, and food. There are food trucks on-site and no grills/open flame cooking is permitted.

Explore Local Trails & Parks

While you can't go wrong with a trip to the overlooks and iconic trails of Shenandoah National Park, there are a number of great options closer to town! We recommend the Saunders-Monticello Trail, Biscuit Run Park, or Ivy Creek Natural Area for more leisurely trail options. The Loop de'Ville Festival on September 27th is a great chance to explore the 20+ mile Rivanna Trail. This festival is a full day of guided group hikes, walks, runs, and bike rides. 👉 6 Reasons to Take Part in the Loop de'Ville Festival

E-Bike and Cycling Adventure

Whether you're a season cyclist or an e-bike cruiser, there's something for everyone in Charlottesville and Albemarle County.

👉 Find more biking recommendations, including routes and rentals, here.

6. Fresh Flavors & Local Finds

Browse Local Farmers Markets

Charlottesville's markets are beautiful in the early fall, with seasonal produce, locally made treats, and plenty of artisan goods for the early holiday shoppers out there. On Saturday morning, head Downtown for the Charlottesville City Market or the Farmers Market at IX for everything from apples and heirloom tomatoes to crab cakes and fermented food. The Scottsville Farmer's Market is also worth the Saturday morning visit and only a short drive out of town. For a midweek fix, check out Farmers in the Park on Wednesdays. 👉 See a full list of farmers markets here

Discover Hidden Gems

After a concert, game, or night out on The Corner, Charlottesville has plenty of spots to satisfy your foodie cravings! 👉Check out these 10 Must-Try Hidden Gem Restaurants, recommended and written by expert foodie Rachel Buccola (cville.foodie)!

Enjoy Alfresco Dining

September brings cooler weather and the first hints of fall foliage, making it the perfect time to indulge in outdoor dining! Stroll the historic Downtown Mall and dine outdoors for a quintessential Charlottesville experience. Or venture out of the city with some takeout, most wineries allow outside food and offer open seating, sunset views, and live music!

New Spots to Try in September 2025

7. Make Plans to Attend These Events

Book Your Stay

September is a buzzing month in Charlottesville -- weekends will fill up quickly -- especially those surrounding UVA home football games! So, plan ahead or consider coming during the week for greater hotel availability and lower rates. Many of our area accommodations make a great getaway for remote work!

Places to Stay

Charlottesville and Albemarle County offer visitors a wide variety of places to stay, including resorts, hotels, inns, bed and breakfasts, cabins, and vacation rentals.

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Sip and Stay: Winery Lodging Learn More
Getting Here & Getting Around Whether your preference is wheel or wing, Charlottesville has an abundance of transportation options that get you where you need to be. Learn More

There's Always Plenty to Do in Charlottesville!

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