October in Culpeper

Blog and Press

October in Culpeper


Fall has officially arrived! Now is a great time for a road trip for a weekend getaway in Culpeper, your destination for rich history and modern charm. The scenery is changing daily and this fall foliage predictor map shows the coming days being optimal for leaf peeping in the Piedmont of Virginia. Plan your trip around an event or the predicted foliage schedule and we’ll see you soon during your wanderLOVE travels.


October 2 – It’s a fun weekend at Andora Farm for those who love or want to experience a bit of agriculture and cowboy culture. Team Penning Practice begins at 7 p.m. and is the starting point for a full Cattle Drive Weekend immersive experience. Bring your horse and enjoy trail riding, cattle driving, and homecooked hot meals. Another Cattle Drive Weekend begins October 30.

October 2 – Kick off the spooky month with a fun painting class called “Feelin’ Witchy” at Wine and Design. Bring your besties with you to create your own versions of a “Hocus Pocus” themed canvas. Registration required.

October 2 – The month of live music at Prince Michel Vineyard & Winery and Tap 29 Brewery kicks off at 5 p.m. with Jimmy O.

More live music is available Thursday through Saturday evenings at Grass Rootes in downtown Culpeper. Enjoy a meal on the front deck or the back deck; both locations are wonderful. Monitor their Facebook page for entertainment announcements.

October 3 – The 2020 Culpeper Cycling Century is an intense 30-, 60-, or 100-mile cycling course. It’s already full but that doesn’t mean you can’t be a spectator cheering on the 500 adrenaline junkies from a spot along the course. Please remember to maintain a distance from other parties and wear a mask where and when appropriate.

October 3 – Firelight Yoga Nidra is a “yogic sleep” – a “guided meditation focusing on breath awareness, intention setting, visualization, and deep relaxation. The practice is restorative and reduces stress, and will be held outside, weather permitting. Hosted by Pranapiloga, this event requires registration.

October 3 – V-Dubs in the Vineyard IV is a classic Volkswagen car show held at Mountain Run Winery. Drive your sweet ride on over for a chance to take home a trophy, or simply enjoy perusing the cars as an appreciator. Trophies will be awarded at 3 p.m.

October 4 – Get ready for the holiday season by attending the 13-inch Christmas Tree with Lights paint session at Glazed Up. Allow three hours to paint your very own ceramic tree, then leave it for firing. When it’s finished, a light kit will be included. The painting session is limited to eight registered people.

October 6 – National Night Out in Culpeper is hosted by the Culpeper Police Department in various neighborhoods around town. Families are invited to join in festive, but distanced, fun with our local law enforcement officers in a celebration of community.

October 7 – Add a beautiful bit of fall décor to your home when you create your own Autumn Lantern canvas at Wine and Design. Register for the 6:30 p.m. class and bring a pal to enjoy a bottle of wine and paint along with you.

October 6 – Offered each Tuesday this month at Lenn Park Activity Room, the Drawing & Painting class hosted by Culpeper County Parks & Recreation will explore water-based painting, oils, charcoal, pastels, and more. Register for the class that aligns with your age group (6-10, 11-17, or 18 and older) and a supply list will be provided to you ahead of time.

October 9 – CulpeperFest 2020 is an event thrown by the Culpeper Chamber of Commerce and features plenty of family friendly activities like prizes, food, plenty of vendors, and large vehicles kids love to see. Expect one-way lanes to move through the event and please wear a mask. If you do not have one, one will be available to you. CulpeperFest will be from 4 to 8 p.m. at Cyclone Stadium at Eastern View High School.

October 9 and 24 – Madison Highway Band will play TWICE this month at Davis Street Pier in downtown Culpeper. Known for their classic, Southern, and 90s rock, as well country of the same decades, their song list is 300-strong and delivers something to sing and dance to. Gigs begin at 10 p.m.

October 10 – Culpeper Recreation Club Fall Fest is an escape for families looking for live music, face painting, hayrides, cupcake decorating, a bonfire, and more. The event is from 10 a.m. to 4 p.m.

October 10 – Armored Practice is likely a surprising event to some, but intriguing and exciting to others. Walk into a medieval battle; true steel-on-steel armored combat at Mountain Run Winery. If you have no sword to wield, feel free to watch with a glass of wine, mead, or cider from the winery.

October 11 – Visiting a Civil War battlefield is one thing, but traversing from one to another via horseback is another. Join a unique opportunity of riding the Historical Cedar Mountain Trail Ride on horseback. Landowners have given permission for this ride to occur, and it’ll go off without a hitch rain or shine. Lunch is included in the fee. The ride is for ages six and older and the registration deadline is October 5.

October 11 – Art Buzz Kids is a program built for kiddos and their family. Register for the Family & Me Pumpkins painting class created for a parent and child, who will create a two-canvas masterpiece together. Register online before this class fills up!

October 12-18 – Everyone loves dining around, and you can consider yourself officially invited to enjoy Culpeper Downtown Restaurant Week! Special three-course menu items are rolled out for the week at eight participating dine-in restaurants and four carry-out restaurants.

October 14 – Each Monday and Wednesday from now through November 30, homeschoolers aged 6 to 11 are welcome to join in the Little Tigers Karate Level I class hosted by Culpeper County Parks & Recreation and held at Lenn Park. From 1 to 2 p.m., your little karate kid can learn a bit of discipline, self-control, and respect.

October 15 – There’s nothing like a fall road trip, and our proximity to great scenic drives gives us plenty of beautiful views to choose from. Capture such a drive with a canvas painted by your own hand. Register for the “Fall Road Trip” painting class to dapple your own foliage onto a scene of winding road. Find more fall and Halloween classes offered by Wine and Design.

October 15-18 – FlowJam Festival 2020 at Verdun Adventure Bound is four days of hippie vibes, including yoga, music, dance, and art. Come flow with us on 55 acres for a bit of nature, healing, and creativity. The event is capped at 250 attendees. Please plan to maintain your distance with spaced classes, camping, and temperature checks at the gate.

October 17 – The Fall Festival and Craft Fair at Mountain Run Winery will feature live music by David Gilmore and South Canal Street, 30+ crafty vendors, excellent food, and of course, great wine, mead, and cider from the winery. Bring your chair and plan to spend the day. Fresh apple cider and s’mores are planned! The event is from noon to 7 p.m. and there is plenty of room to spread out.

October 17 – Toss a bit of cornhole for charity! The Cornhole Tournament Fundraiser at Old Trade Brewery is 3 to 6 p.m. and benefits the SAFE Program, a community initiative providing services for survivors of domestic violence and sexual assault for all ages, gender, race, etc. Bring the kids for playground fun as you work your way through the bracket to reach for cash prizes.

October 17 – The 7th Annual Benefit Fun Show at Conerstone Horsemanship welcomes riders of all ages, experiences, and disciplines to compete in classes like Ranch Reigning, Long Trot Race, and Jackpot Dummy Roping. Gates open at 8 a.m. and the show begins at 9 a.m.

October 24 – This Saturday is the last of the summer season for Yoga at Mountain Run Winery. Registration is required so that organizers can adhere to social distancing guidelines. All abilities are welcome. Stick around after class for a glass of wine.  

October 24 – The Unsuitables Party at Mountain Run Winery is a grand time of wine, music, and dancing from 5 to 8 p.m. with the sounds of “rock and roll with a twist of funk and soul.” Bring a chair and enjoy!

October 24 – What would October be without some ghostly fun?  Plan to join the Spirits of the Graffiti House featuring Culpeper Paranormal to tour the Graffiti House, hear the multitude of historical stories, and enjoy treats. The paranormal gang will be on hand to answer questions and share their experiences of investigating this historic site.

October 25 – Mountain Run Winery is hosting their first fall Paint Event ever and you’re invited to get a little crafty with them. All the supplies are included for you to complete a 10x20 fall themed canvas, plus a glass of wine. Register and we’ll see you there from 1 to 3 p.m.


Toast the beautiful fall season with a visit to Culpeper. If you need anything, give us a call at 1-844-490-2577 or we’ll be glad to send you a copy of our Visitors Guide.