Things to Do in Charlottesville and Albemarle County: October 2023

Sip and stay awhile because October is Virginia Wine Month! There are more than 40 wineries in the Charlottesville area offering a variety of experiences, so you can truly customize your visit based on your unique preferences. From cozy tasting rooms to grand outdoor seating areas and every layout in between, local wineries are frequently hailed as one of the top activities in Charlottesville and Albemarle County. Many wineries are family and dog-friendly, some routinely offer food trucks and live music, while others have refined their experience to be suited for ages 21+.

There’s another special reason to celebrate Virginia Wine Month in Charlottesville and Albemarle County this year. Our region, the Monticello Viticultural Area, was recently nominated as one of just five Top Wine Regions in the world by Wine Enthusiast, putting us in the same category as wine destinations like Lambrusco, Italy and Provence, France.

If you’re looking for a fun way to celebrate, we recommend attending the second-annual Two Up, Wine Down wine festival hosted at the Jefferson School African American Heritage Center on Sunday, October 29, 2023. Taste 10+ wines, enjoy some of the best of Charlottesville’s local food scene, and get to know a diverse set of wine experts and enthusiasts. This event is bound to sell-out – so snag your tickets soon!

Leaf peepers, raise your hands! For some, the sole purpose of an October visit is to witness Mother Nature’s annual color show. Typically, the Charlottesville area enjoys peak fall foliage between October 15-30, though it can vary from season to season. Plan to have no plans, other than leisurely drives along the Blue Ridge Parkway or through Shenandoah National Park, both of which can be reached in 30 minutes from downtown Charlottesville. Or, discover fall foliage along some of the beautiful roadways traversing the scenic countryside of Albemarle County. Make sure to have your cameras and smartphones at the ready to get some truly spectacular shots you'll treasure for years to come!

If you’re planning to drive out to neighboring Shenandoah National Park for fall foliage, follow the park’s Fall Color Updates. Keep in mind that wait times to enter the park increase during peak foliage – so be prepared by purchasing a park pass ahead of time! The America the Beautiful National Park Pass ($80) can be purchased at Public Lands in Charlottesville and provides access to all national parks for one calendar year.

October is prime season for putting on your best cozy attire and heading out to one of Charlottesville & Albemarle County’s orchards where you can enjoy all the special treats of the season like hot cider, donuts, and of course – pumpkins!

October weekends are the busiest times for our area orchards all year! Some tips to plan your visit:

• Henley’s Orchard in Crozet offers Henley Fest every weekend in October complete with hayrides, live music, and hot apple cider (both the hard kind and the kid-friendly kind!).
• Advance tickets are required to visit Carter Mountain Orchard on Friday – Sunday throughout October. They also offer a drive-through experience during these times. If you plan to visit on these days, you can also take advantage of food trucks on-site. Tickets are not required for entry Mondays – Thursdays.
• At Chiles Orchard, tickets are required for pick-your-own experiences on Saturdays & Sundays in October. Tickets are not required for Monday – Friday picking.

This brings us to our next hot tip for visiting Charlottesville and Albemarle County in October: consider a Sunday – Thursday stay. Guests will experience the same beauty and loveliness our area has to offer; without the crowds and wait times. Plus, hotel rates will dip a bit midweek, allowing room in your budget for even more fun!

Immerse yourself in the captivating fall foliage and crisp autumn air by getting out on the trail. Whether you seek a leisurely stroll or a more intensive climb, there’s a hike to suit all desires and abilities in the Charlottesville area. Your efforts will be rewarded with beautiful views, and a rainbow of colors as a backdrop – perfect for those seasonal snaps. Check out our best hikes blog post to see which is the best fit for your next adventure.

Foxfield Races – Sunday, October 1st
Don’t forget your floppy hat! The fall races feature lots of kids activities, so be sure to bring the whole family. Click here for more information.

Home UVA Football game
UVA Football is playing at home on October 7th vs the College of William & Mary. Make a weekend of it and plan to arrive on Thursday or extend your stay through Monday to take advantage of some of the fall activities in the area. Stop by the UVA Alumni Hall pregame tailgate to grab enjoy some food and drinks, get recommendations about the area from our Mobile Visitor Center, and ride the complimentary shuttle to Scott Stadium. For ticket information, click here.

Crozet Arts & Crafts Festival – October 7 & 8
This twice annual juried arts and crafts event draws talented artisans from states away! The festivals were started in 1980 to benefit Claudius Crozet Park, a non-profit community owned and operated park located in Crozet, just 15 minutes west of Charlottesville. Today, the festival draws thousands of visitors from near and far, and features live music, food trucks, and craft beverage tastings, in addition to the arts and crafts available for purchase. Click here for more information. And on Saturday October 7, the Mobile Visitor Center will be at the festival to help you with any other questions you may have!

Archaeology Open House at Monticello – October 7
October is Virginia Archaeology Month and Thomas Jefferson’s Monticello will host its annual open house for visitors on Saturday October 7. The open house will include exhibits of recent discoveries and walking tours of the pieces of the property that have vanished from view.

This year’s Walking Tours will visit Site 30, an archaeological dig that is revealing important information about enslaved agricultural laborers at Monticello as well as the precolonial activities of Indigenous communities on this landscape. Walking Tours leave from the Bronze Plantation Model in the Visitors Center at 11 a.m., 1 p.m., and 3 p.m.

Crozet Trails 5K & Family Fun Run – October 28
The annual Crozet Trails 5k is back and a great event for runners and walkers of all ages! Attendees can choose to run the 5K, 1K Family Fun Run, or the new 10K race.

Whether you’re looking to set a new race time or just to stroll the beautiful trail with a dog on leash and coffee cup in hand, this event is for you. After the race, stick around for live bluegrass music and beer from local brewery Starr Hill.

Virginia Film Festival – October 25-29
The Virginia Film Festival (VAFF) is gearing up for its 36th year with another outstanding array of films and events coming up from October 25-29 at venues on the Downtown Mall and on the Grounds of the University of Virginia. Each year, the VAFF takes audiences beyond the screen with dynamic discussions following most of its films. Expect to hear from leading industry and cultural voices and University of Virginia experts as they discuss topics related to the films’ subjects and themes.

The Film Festival’s full line-up will be announced Tuesday, September 26th and tickets go on sale starting Friday, October 6th!

We can’t wait to see you in Charlottesville and Albemarle County this October. For a complete list of October things to do in Charlottesville, visit our calendar of events. If your schedule permits, consider a midweek stay (or extend your stay to the midweek) to avoid crowds and traffic – it will make the experience even more magical. Please share your experience with us on social by tagging @charlottesvilleva on Instagram – we’d love to share it with future visitors. We can't wait to welcome you to Charlottesville and Albemarle County soon!