Live Music in October


“Vocal powerhouse, Maddi Mae Hicks, serenades with soulful folk, blues, and country tunes accompanied by her acoustic guitar, beautiful fingerstyle techniques, and looper.”

Friday, October 5 – Headmaster’s Pub with Noah Taylor Stidham & Kimber Herron

8-11pm, no coverHeadmaster's Logo

12018 Lee Hwy, Sperryville, VA 22740

(540) 987-5008

Noah Taylor Stidham is a multi-instrumentalist from Richmond, VA who plays upright bass with Brandy Station Co. and Blue Ridge Avalanche; he may be playing some guitar, keys, and pedal steel throughout the night as well. Kimber Herron is a multi-instrumentalist from Berryville, VA; he’ll be playing lead on something(s) – it’ll be a surprise for all of us!

From Headmaster’s Pub“Come enjoy our famous Ayrshire Farms grass-fed burgers and local beers. Then stay for the area’s best live music every Friday and Saturday night. From buffalo wings to greek salads and heaping corned beef Reubens, we’ve got something for everyone to enjoy. Kids [and adults] need something to do? The adjoining arcade features video games, air hockey, skeeball, bowling, and more [pinball, foosball, pool tables]. Enjoy views of Old Rag mountain and the Schoolhouse Nine Par 3 Golf course from our outdoor deck.”

Saturday, October 6 – Clarke County Farmers’ Market

9:30-11:30am, no cover

100 S Church St, Berryville, VA 22611

More about the Clarke County Farmers’ Market: CLICK HERE.

Morning of Saturday, October 13 – Orlean Day at The Orlean Market

10:00-11:30am, $5/children <12 FREE

6855 Leeds Manor Rd, Marshall, VA 20115

(540) 364-2774

From the Celebrate Orlean Day Facebook page: “A family-oriented day of fellowship, fun, and food will be held in the village of Orlean on Saturday, October 13th, 2018. This is our way to celebrate the beautiful place that many of us call home and to recognize some of the people who help make it special. Activities for the day: photo contest, apple pie contest, Orlean Family Award, vendors, and a moon bounce, obstacle course, and games for the kids. Local beer and wine for the adults. Featuring music by the local artists listed below:


10:00-11:30am / Maddi Mae 
Providence Church Choir 
Bicentennial Award & Music
1:00-3:00pm / Elizabeth Lawrence Band
3:30-5:30pm / Cobbler Mtn. Grass Band
6:00-8:00pm / Tower Blues Band”

Evening of Saturday, October 13 – Magnolia Vineyards & Winery

Magnolia2-5pm, no cover

200 View Town Rd, Amissville, VA 20106

(703) 785-8190

From Magnolia Vineyards & Winery“We like to refer to ourselves as a Mom & Pop, small production, boutique winery . . . We strive to integrate Olde World hospitality and charm with a casual, laid back and relaxing modern-day atmosphere. We have interior seating for ~25, exterior picnic tables and porch seating for another 20 or so and, of course, plenty of open ground for picnickers, either right outside the tasting room or on the hilltop by the Black Walnut tree with views of the Blue Ridge mountains.

We offer cheese pairings with our wine tastings and a variety of cheese and crackers on premises for sale. Visitors are welcome to come out and spend the day enjoying the views and occasional local wildlife sighting of deer, wild turkey or maybe even Red the vineyard fox and ‘escape the madness’. No stress, no pressure (just magnificent wines)!”

Saturday, October 20 – Orlean Market

7-10pm, no coverORLN MRKT

6855 Leeds Manor Rd, Marshall, VA 20115

(540) 364-2774

From Orlean Market & Pub“It’s a short drive back in time to the village of Orlean. Cozy up in the late 1800s restaurant and pub. Send the kids outside to fly on the rope swing. Or, if the weather is so inclined to be warm, watch the sunset on the patio amidst the ivy and lights.”