Charlottesville Fall Festivals – Fall 2021 VA Events

Orange Street Festival - Orange, VA - Sep 11 to Sep 11, 2021
This popular festival features over 150 vendors, specialty food, live music and beers, and kids’ zone. Located along Main Street and inside Taylor Park. Free and open to the public.

Lynchburg Beer & Wine & Cider Festival - Lynchburg, VA - Sep 18 to Sep 18, 2021
Over 5,000 guests attend the event at Lynchburg City Stadium. Enjoy samples of over 75 different craft beers, ciders, and wines from Virginia, plus local artisans, food, and live music. The Sampling Admission Ticket includes 10 4-oz samples of beer and cider, plus unlimited wine samples and a commemorative beer or wine glass.

Devils Backbone Oktoberfest - Roseland, VA - Sep 25 to Oct 31, 2021
Fall is finally here and what better place to celebrate than in the heart of the Blue Ridge Mountains at Devils Backbone Basecamp Brewpub & Meadows. Free entry with pay-as-you-go experiences like the $5 hay bale maze, Oktoberfest food specials, seasonal produce vendors and more

Fallapalooza - Orange, VA - Oct 1 to Nov 27, 2021
For 2021, a virtual fall festival again. Orange Chamber of Commerce is hosting a photo and video entry contest that will consist of a person’s favorite photo/video of an Orange County destination, location or business.

Fall Fiber Festival - Montpelier Station, VA - Oct 2 to Oct 3, 2021
Fleece sale, fiber and crafts vendors, music, sheep dog trials, demonstrations, animal exhibits and more.

Flippin-Seaman Apple Butter Makin’ Festival - Tyro, VA - Oct 2 to Oct 16, 2021
Watch Silver Creek & Seamans’ Orchards make apple butter the old fashioned way, on the first and third Saturday in October.

Graves Mountain Resort Apple Harvest Festival - Syria, VA - Oct 2 to Oct 17, 2021
For 2021, three weekends with potentially two sessions per day. Normally: Features Bluegrass music, arts and craft vendors, good food, hayrides, and lots of apples and apple butter making.  Also pick your own apples from the orchard.  Located at Green Mountain Lodge, weekends only. Free Admission and Free Parking.

Frontier Culture Museum Oktoberfest - Staunton, VA - Oct 2 to Oct 2, 2021
German food, beer garden, games and music at the Cochran Pavilion. Location: Frontier Culture Museum, 1290 Richmond Ave Staunton, VA 24401

Cyrus McCormick Farm Mill Day - Raphine, VA - Oct 2 to Oct 2, 2021
The main attraction of the day is the operation of the McCormick Grist mill. Built in the late 1700’s, the mill has been fully restored to working order. In addition to the mill operation, there are many traditional craft vendors, music and food (provided by the Raphine Volunteer Fire Department. There will also be short tours to view and discuss the agricultural research being conducted at the Shenandoah Valley AREC. This is a free event.

Gordonsville Fried Chicken Festival - Gordonsville, VA - Oct 2 to Oct 2, 2021
Gordonsville is famous for its fried chicken, which was served to passengers of trains stopping in town during the late 19th and early 20th centuries by local women carrying platters of the delicacy on their heads. Nationally-known at that time, Gordonsville’s fried chicken earned the town the nickname of “chicken-leg center of the universe”. To celebrate this legacy, this festival, held from 11 am – 5 pm at the Gordonsville Fire Company Fair Grounds, will feature a fried chicken and pie contest, wine garden, and numerous craft and artisan vendors. This is a rain or shine event!

Hands and Harvest Festival - Monterey, VA - Oct 8 to Oct 10, 2021
The annual Hands & Harvest Festival is a celebration of fall in this rural, mountain community. The event features an arts & crafts show, live entertainment, fall-themed menus and a self-guided Harvest Trail that takes travelers to unique locations throughout the county, where visitors can enjoy experiences of farming, food, and more. You may find yourself pressing cider or stirring apple butter, enjoying one of Highland County’s sugar camps in the off-season, or climbing a fire tower to watch a beautiful sunset or sunrise. Enjoy a free concert Saturday night at 7 pm at the Highland Center, which also includes FREE cider from award-winning Big Fish Cider

Virginia Fall Foliage Festival Art Show - Waynesboro, VA - Oct 9 to Oct 10, 2021
Held in downtown Waynesboro, where 150+ artists and fine artisans will show their works at this juried outdoor festival, plus regional craft beer and gourmet food trucks.

Shenandoah Fall Foliage Bike Festival - Staunton, VA - Oct 15 to Oct 17, 2021
A full weekend of sightseeing and bike riding on any of 11 routes covering hundreds of miles among the fall foliage in the Shenandoah valley, with rides for all ages and abilities. Features breakfast and lunch activities.

Elkton Autumn Days Arts and Crafts Festival - Elkton, VA - Oct 16 to Oct 17, 2021
The weekend will be filled with arts, crafts, music and food all in the heart of the Town of Elkton, VA nestled between the Blue Ridge and Massanutten Mountain ranges in the Shenandoah Valley. The festival is free to attend and is located on West Spotswood Avenue in Downtown Elkton.

Heritage Harvest Festival - Charlottesville, VA - Oct 23 to Oct 23, 2021
Celebrate Thomas Jefferson’s legacy with this educational and family oriented festival held at Monticello. Tastings and chef demos, kids’ activities, workshops and tours, shopping, gardening, and more.

Stanardsville Oktoberfest - Stanardsville, VA - Oct 23 to Oct 23, 2021
Enjoy great food, wholesome family-friendly fun, wonderful music and amazing beer. Enjoy the homebrewers contest and vote for your favorite recipe from among the best up-and-coming home brewers in the state. You can also enjoy some of the region’s best local breweries on tap. A costume contest at 2 PM will provide whimsy for the young and young at heart and story tellers gather as evening shades fall to enthrall and inform you with tales of ghostly delight as history comes alive. Free general admission. Haunted tours of the town will start immediately following the event.