50th Annual Downtown Orange Street Festival

Saturday, September 6th 2025 - 10:00 am - 4:00 pm at Town on Orange
East & West Main Street

The Downtown Orange Street Festival is an annual community event, with over 150 artisans, craft and commercial vendors, a variety of food and beverage vendors, live music, and a kid’s zone. This family-friendly festival draws over 5,000 people from all over Central Virginia and is a great venue for community awareness and promotion.

Vendor Registrations accepted until August 1, 2025. CLICK HERE

Early Bird Pricing available until May 31st

Vendors along East & West Main Street, Short Street, and Taylor Park stage parking lot.

Inaugural Charlottesville Tom Sox Pickleball Round Robin

Saturday, September 6th 2025 - 11:00 am - 3:00 pm at Boar
200 Wellington Dr

Saturday, September 6th from 11 a.m. – 3 p.m.
Boar’s Head Sports Club

$68 per participant (includes organized play, snacks and a signature event beverage)
Rain moves the event indoors.

If you are not able to attend the event but would like to donate, please click here.

Bill Steers 5K

Sunday, September 7th 2025 - 9:00 am at Foxfield Races
2215 Foxfield Track

Get ready to run on September 7th at 9 AM, for an important, community cause: the Bill Steers 5k!

This year, the race will be held during Prostate Cancer Awareness Month to support our goals of raising funds and awareness for prostate cancer and survivorship. All proceeds will be used by the UVA Department of Urology in their ongoing research.

In 2004, Dr. Bill Steers, who was the Chair of the UVA Department of Urology at that time, founded the Charlottesville Men’s Four Miler. Over the decades, the race has raised thousands of valuable dollars for men’s health initiatives and groundbreaking cancer research at UVA. In April of 2015, the Urology community and University of Virginia mourned the loss of this great man. This year we invite everyone to participate in the 21st Anniversary of this event to continue Dr. Bill Steers’ vision, dedication, and legacy of better health through exercise. All are welcome to participate in the Bill Steers 5k this year to help us build a better, healthier future through activity, exercise and innovation.

The event includes a 5k run/walk, food trucks, community health vendors, and a kids’ race!

CLICK HERE TO REGISTER

In addition to the in-person event, there is also a virtual 5k option for those who cannot attend in person.

CLICK HERE TO REGISTER FOR THE VIRTUAL OPTION

Trivia Like It’s 1799!

Thursday, September 11th 2025 - 6:00 pm - 9:00 pm at Michie Tavern
683 Thomas Jefferson Pkwy

Thursday, September 11, 2025 | 6:00 p.m. at the Michie Tavern 1784 Pub

Free to Play | Reservations Encouraged

Come test your historic knowledge while enjoying a pint and some grub at Michie Tavern’s 1784 Pub! Join local quizmaster and Executive Director of the Albemarle Charlottesville Historical Society Olivia Brown as she brings 18th century history to life in this fun and competitive night of trivia. 20% of food and beverage sales will be donated to ACHS in support of local history. Prizes awarded to winning teams and teams should not exceed five members.

Tables will be first-come, first-served and reservations are encouraged. To make a reservation, call Michie Tavern at (434) 977-1234

Celebration Of Life “Yankie John”

Saturday, September 13th 2025 - 4:00 pm at Minutemen MC Clubhouse
276 Lams Dr

Join the Minutemen MC as they celebrate the life of “Yankie John”, beloved President and friend.

It’s all happening on Saturday, September 13th at 4pm and includes good food, a pig roast, good memories, camping, and live music from Richmond’s own, “Double Down”.

A $20 donation is requested with proceeds going to help cover Yankie’s final expenses.

BYOB and camping is encouraged.

MMC Clubhouse, 276 Lams Dr. Gordonsville, VA 22942

No Attitudes/No Glass Bottles/No Pets

Underage Drinking will NOT be tolerated!!

For more info, Contact: “Reinaldo” 540-406-1457 or “Snowman” 434-806-3310 or “Pauly” 434-882-2171

Fork Union Day

Saturday, September 20th 2025 - 9:30 am - 3:00 pm at Fork Union Military Academy
4744 James Madison Hwy

A fun day in Fork Union is scheduled for September 20th with the Fluvanna Leaders for Race & Diversity!

Head to Fork Union Military Academy and celebrate Fork Union Day with vendors, food trucks, and of course, the Parade!

The Fluvanna Leaders for Race & Diversity, along with community partners, are seeking vendors and participants to sign up today!

Vendors and Food Trucks, CLICK HERE to register for this event!

This event is free and will feature live music, food, and a car show!  

Celebrate Fork Union with a fun, family friendly day!  

Creatures Great & Small with Green Dogs Unleashed

Sunday, September 21st 2025 - 12:00 pm - 4:00 pm at Scottsville Pavilion
125 Fleet St

Green Dogs Unleashed invites you to come out and enjoy a day that’s sure to be enjoyed by the entire family. There will be vendors, animal rescues and food trucks to enjoy for the afternoon!

Green Dogs Unleashed is a non-profit organization committed to rescuing animals in need, rehabilitating them and professionally training them to become Therapy dogs. They then place them in homes to give back to the community,

Green Dogs Unleased is pleased to present their new program, “Bark Rangers“!  Ready to take your training beyond the backyard? Bark Rangers offers interactive, intensive workshops focused on practical skills, adventure training, and teamwork. Earn badges for every new skill mastered, build confidence through real-world experiences, and connect with a community of like-minded dog lovers!

Gordonsville Fried Chicken Festival

Saturday, October 4th 2025 - 10:00 am - 4:00 pm at Cooke Park
100 US-33 #298

NEW – EVENT LOCATION – SOUTH MAIN STREET, GORDONSVILLE, VA 22942
TOWN HALL NORTHSIDE PARKING LOT – COOKE PARK

Gordonsville is famous for its fried chicken. In the late 19th and early 20th centuries, local women carrying platters of the delicacy on their heads served it, along with pies and coffee, to passengers of trains stopping in town. Nationally known at that time, Gordonsville’s fried chicken earned the town the nickname of “chicken-leg center of the universe”.

Click on this link to view VPM’s Hidden History with Brian Bullock‘s brief about Gordonsville’s fried chicken heritage.

Each year, we celebrate this heritage annually at our Famous Fried Chicken Festival. This year’s festival will be held on Saturday, October 4th at the new location the Gordonsville Town Hall northside parking lot! The event will feature a fried chicken and pie contest, wine garden, and numerous craft and artisan vendors.

We couldn’t have this festival were it not for the generous support of our sponsors:

• East of Maui Coffee
• Blue Ridge Bank
• Ventresca Family Insurance
• Southwest Mountain Vineyards
• Ragged Mountain Running
• Journey Church
• Blossman Gas

There is no cost to attend the festival, but there is a $5.00 fee per person to enter the wine garden (proof of age required–only those 21 and older permitted in the Wine Garden). CASH OR CHECK ARE PREFERRED METHODS OF PAYMENT.

NO DOGS PERMITTED AT THIS EVENT: We love pets, and we know you love yours. However, we ask that you leave your pets at home as they are not permitted at this event (service dogs excluded, of course).

This is a rain (non-hurricane) or shine event!

COOK-OFF CONTEST
Join in on the fun at the Fried Chicken Festival and become a cook-off contestant! Cook-off guidelines and contest entry forms may be accessed by clicking on these links:
Fried-chicken contest
Pie contest

Brag about and showcase your family’s fried chicken recipe! Watch people’s mouths water in anticipation of your greatest pie yet! And best of all – in addition to gaining the ultimate bragging rights for the next year, you could win one of the following prizes:

Fried Chicken Contest:
1st place – $100
2nd place – $75
3rd place – $50

Pie Contest:
1st place by category (fruit, cream and custard) – $75

VENDORS
To reserve your spot as a wine or craft/artisan vendor, click on the links below for an application form:
Wine Garden Vendor Application
Craft/Artisan Vendor Application

PAYMENT OF FEES
Contest fees, vendor registration fees, and wine garden entrance fees may be paid online through PayGov.us using code #37828**. Entry to the Wine Garden will be permitted upon showing your PayGov purchase confirmation code to personnel at the wine garden entrance, and upon proof of age.

Only those 21 and older are permitted in the Wine Garden.

**Please note: there is a convenience fee charged for each transaction on PayGov. The fee is $1.00 for any transaction under $33.00, and 3% for each transaction over $33.00. 

NEED MORE INFORMATION?
For more information, contact Clair Clark, Gordonsville Interim Visitor Center Director, mail Mrs. Clark at cclark@gordonsville.org

We hope to see you at the Festival!

Beers, BBQ & Beautiful Rides

Saturday, October 11th 2025 - 11:00 am - 5:00 pm at Belmont Farm Distillery
13490 Cedar Run Road

Fluvanna Family Fall Festival

Saturday, October 11th 2025 - 11:00 am - 4:00 pm at Pleasant Grove Park
271 Pleasant Grove Dr

A celebration of Fluvanna’s rural and agricultural heritage and history, the 2025 Fluvanna Family Fall Festival!

The Festival will be a half-day, family-friendly event to bring together local artisans, businesses, and community members to kick off Fall in a vibrant celebration of Fluvanna’s rich history and agricultural heritage.  Enjoy local foods, handmade crafts and jewelry, art, master gardeners, historical exhibits, local farmers, live music, and activities for kids, all wrapped up in a congenial, small-town atmosphere.

We will also be accepting food and other donations on behalf of MACAA (Monticello Area Community Action Agency) and local non-profits.  Last year, the Festival donated more than 850 pounds of food to families in need.

Free admission for adults with the donation of one nonperishable food item (or $2 cash). Free for kids!

2025 registration for vendors, exhibitors, and food trucks is now open!!!

Sign up now by CLICKING HERE and using our Google Form 

Questions? Email us at: FluvannaFallFestival@gmail.com. We can’t wait to see everyone in October! 🍁