September in Charlottesville: Top Things to Do - Fall Festivals, Football, Food

Summer is winding down in Central Virginia, and cooler days are on the horizon — but we’re not ready for pumpkin spice and sweaters just yet.

September is one of the liveliest months in Charlottesville and Albemarle County, filled with festivals, music, outdoor adventures, and seasonal flavors.

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. Embrace All Things UVA

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! Take a look at this year's schedule here. 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.

Explore Grounds

Catch the energy of campus in full swing! Stroll the UNESCO World Heritage Site with a student-led or self-guided tour, admire Thomas Jefferson's iconic Rotunda, enjoy a picnic on the Lawn, and browse the unique shops and restaurants along the Corner.

3. Go to a Festival or Special Event

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

4. Enjoy Live Music All Month Long

Wander the 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

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. To get you started, we recommend checking out Durty Nelly's, The Batesville Market, Holly's Diner, and Rapture!

Relax and Wine Down at Wineries and Cideries

Many of Charlottesville & Albemarle County's wineries and cideries keep the good vibes going all season long with live music and scenic views - the perfect way to spend a relaxing afternoon or evening. Here are a few to get you started:

5. Outdoor Experiences, Adventure, and Recreation

Pick-Your-Own Fields

Apple picking season will be here by mid-September and reservations are required for weekend picking until 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

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.

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 on our website. Here are a few recommendations to get you started:

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. Take a look at this full list of farmers markets in the area.

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 Hidden Gem Restaurants and Late Night Eats 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 grab some takeout and venture out of the city - most wineries allow outside food and offer open seating, gorgeous views, and live music!

New Spots to Try in September 2026

Book Your Stay

One day is never enough to experience everything Charlottesville & Albemarle County has to offer. Extend your adventure with an overnight stay and wake up ready to explore award-winning wineries, historic sites, mountain trails, local restaurants, and unique shops. Browse our Places to Stay page to find the perfect accommodations, then visit our Guides and Itineraries page for even more ways to build your ideal trip!

One blog couldn’t possibly capture everything that’s happening in Charlottesville and Albemarle County! Head over to our upcoming events page to stay up to date on all the latest happenings in the area.

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