Vendor Spotlight: Chester Street Tavern

We went as a triple date, three couples out for a night, and left feeling like we had spent the evening with old friends instead of strangers at a bar. That is the thing about Chester Street Tavern. The regulars sitting near us, the band on stage, even the people waiting at the bar, all of it just felt like our people. A lot of that comes down to Jim Justice, the owner, who is beyond friendly. He makes you feel welcome the second you walk in.

‍ ‍Jim is a retired Army veteran who spent nine of his twenty years of service stationed in Germany, where his taste for beer culture took hold. He opened the tavern inside a restored 1806 home, reportedly the third-oldest standing building in Front Royal, and built the whole concept around a simple question: how did they do beer and food when this house was first built. He incorporated under the name Virginia Brewing Company after learning he was the seventh person in Virginia history to use that name, tracing back to an original Roanoke brewery from 1890. He has kept the menu just as simple, five beers on tap, five dollar pints, what he calls protesting inflation.‍ ‍

Walk in and you land in a cozy room with a fireplace, couches, and a long bar, the kind of space that makes you want to settle in and stay a while. There is a small stage area inside for bands and gatherings, and out back the patio opens into several nooks and crannies with couches, tables, and chairs tucked into corners, each one its own little hangout spot. The bands lean into 60s, 70s, and 80s music along with folk, and Jim dresses the whole place up for every season. Their Halloween night has turned into a real event, complete with live bands and a costume contest voted on by the patrons themselves.‍ ‍

Jim has also built the tavern into a hub for causes bigger than a night out. Their Salute to Service event, held each Memorial Day weekend at the Main Street gazebo in partnership with the Town, has featured Grammy-nominated performer Sam Tate and raised support for the Able Forces Foundation and the Farmer Veteran Coalition of Virginia. It is the kind of thing you would expect from a veteran who built his whole business around bringing people together.‍ ‍

For an offsite or retreat looking for an evening that feels less like a scheduled activity and more like hanging out with friends, Chester Street Tavern delivers that without even trying.‍ ‍

Visit chesterstreettavern.com to learn more about Chester Street Tavern. When you are ready to build an offsite that feels like hanging out with old friends, make Headwaters your first call. Headwaters — The Passage | headwatersretreats.com

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