15 Winchester Area Live Music Hot-Spots

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Flickr image by Richele Cole (embedded), taken at the Bright Box Theater

It took a few months of living here (probably because I have two little kids in my house) to start to grasp the depth of the live music scene in the Winchester area.  With all of the hyper-talented SU Conservatory students floating about our community, I figured there were live performances going on all over the place.  Now, after devoting some serious time to find out about more and more cool spots to catch some live tunes, I decided it might be nice to try and put it all down in one place.  As always, if I missed something here, don’t hesitate to let me know.  And get out there and enjoy!



Backseat Bar and Grill

Image from Backseat Bar & Grill’s Facebook page

Country, blues and acoustic fill much (but not all) of the regular live music bill at this local favorite eatery. 104 Full House Dr, Winchester, VA 22603; (540) 665-9033. Click here for a schedule of upcoming shows.


Blue Fox Billiards

Flickr image by PhyllisLynn (embedded)

Local, regional and national acts including country, metal, bluegrass and more. 1160 Millwood Pike, Winchester, VA 22602; (540) 665-2114. Click here for a schedule of upcoming shows.


The Bright Box

Blue Heaven
Flickr image by Tyler Priola (embedded)

Local, regional and national acts of every kind located in the heart of Old Town Winchester. 15 N Loudoun St, Winchester, VA 22601; (540) 665-2878. Click here for a schedule of upcoming shows.


Escutcheon Brewing Co

Image from Escutcheon’s Facebook page

Winchester’s original craft brewery features regular acoustic shows in their tasting room area. 142 W Commercial St, Winchester, VA 22601; (540) 773-3042. Click here for a schedule of upcoming shows.


Hopscotch Coffee & Records

Live Music at Hopscotch Coffee and Records

Image of Fletcher C. Johnson performing from Hopscotch Coffee & Records Facebook Page

One of our popular local coffee spots, patronized regularly by nearby Shenandoah University students. Occasional acoustic live music on tap in this eclectic coffee/record shop with outstanding locally roasted beans; (540) 514-5356. Click here for a schedule of upcoming shows.



Image of Engine No. 9 from Mimosa’s Facebook Page

This local Asian fusion restaurant offers an open mic every Thursday, as well as regular local original artists from country to jazz to electronic dance music (EDM). 202 Grocery Ave # 101, Winchester, VA 22602; (540) 545-8482.  Click here for a schedule of upcoming shows.


Nana’s Irish Pub & Restaurant

Image of Rick Harris from Nana’s Irish Pub’s Facebook Page

Live Irish, bluegrass, and rock music is performed weekly at this hidden gem of great Irish fare and live music right in the middle of Middletown, just steps from the new Gingerwolf Distillery. 7843 Main St, Middletown, VA 22645; (540) 868-9877. Click here for a schedule of upcoming shows.


Shenandoah University

Conservatory Presents 2014 Holiday Gala Concert
Flickr image by Shenandoah University (embedded)

The world-class SU Conservatory turns out regular musical offerings year-round, from free, open rehearsals to nationally known conductors to their ever-popular Summer Music Theatre program.  620 Millwood Ave, Winchester, VA; (540) 665-4569.  Click here for a schedule of upcoming shows.


Sweet NOLA’s Restaurant

Image from Sweet NOLA’s Facebook page

Live music, nationally recognized bands, and crazy-good Southern New Orleans-style food (“Food so good you need a safe word” according to their bumper sticker) in an intimate, funky cool setting.  688 N Loudoun St, Winchester, VA; (540) 667-6652.  Click here for a schedule of upcoming shows.



~Old Town Walking Mall Restaurants~


147 North

Image from 147 North’s Facebook page

An energetic blend of open mic nights, acoustic bands, and even EDM fill 147’s busy weekend music calendar.  147 N Loudoun St, Winchester, VA; (540) 313-4804.  Click here for a schedule of upcoming shows.


Brewbaker’s Restaurant

Image from Brewbaker’s Facebook page

Local and regional live music, many times in conjunction with Shenandoah University.  168 N Loudoun St, Winchester, VA; (540) 535-0111.  Click here for a schedule of upcoming shows.


Piccadilly Public House

Weekly piano bar on Wednesday and Thursday is juxtaposed with lively regional cover bands of every type acoustic performances on weekends.  125 E Piccadilly St, Winchester, VA; (540) 535-1899.  Click here for a schedule of upcoming shows.


Java Kava Bar

Live music at Java Kava Winchester from Facebook
Image from Java Kava’s Facebook page

Sip fresh kava or coffee here at Virginia’s first kava bar while enjoying local young talent performing live (sometimes scheduled, sometimes not!). 16 S Loudoun St, Winchester, VA; (540) 313-7199.  Click here for a schedule of upcoming shows.




James Charles Winery

Someone To Ride The River With

Flickr image by Coy Ferrell (embedded)

Live music every Friday and Saturday evening throughout the year, featuring a range of local, acoustic and SU conservatory performers and beautiful mountain views. 4063 Middle Rd, Winchester, VA; (540) 931-4386. Click here for a schedule of upcoming shows.


Valerie Hill Vineyard & Winery

Image from Valerie Hill’s Facebook page

Enjoy regular acoustic shows on weekends throughout the year in a historic, intimate setting.  1687 Marlboro Rd, Stephens City, VA; (540) 869-9567.  Click here for a schedule of upcoming shows.