An old building, a long bar, a packed house, and an ambience you can feel from the street. Sweet Caroline's is what happens when a kitchen, a bar, and a stage decide to share a room.
at the Newberry Building
Housing Alesatian + Tap Room
An old building, a long bar, a packed house, and an ambience you can feel from the street. Sweet Caroline's is what happens when a kitchen, a bar, and a stage decide to share a room.
Our kitchen is built around wood-fire cooking, scratch-made ingredients, and a chef-driven approach to every dish. We combine technique, creativity, and bold flavors to create plates that feel thoughtful and memorable. From flame to table, everything is made with passion.
-- ON THE WAY --
Rooted in craft and built for experience, our bar features exceptional bourbon, a thoughtful wine list, and award-winning Alesatian Brews on tap
-- ON THE WAY --
Designed by musicians, for music — a room that sounds as good as it feels, showcasing professional local and national artists.
-- HAPPENING NOW --
An open kitchen, a full bar and a live stage come together as a single, live experience — not separate elements. Sound, service, and energy move through the room in real time, so what you see, hear, and taste all share the same live moment. It’s a space built to feel alive.
-- HAPPENING NOW --
Loudoun Street's walking mall has had a hundred lives. Ours starts in a beautifully restored storefront with a copper-warm wood facade, gold-leaf signage, and tall windows that throw light all the way to the back bar. Step in and you're somewhere that feels both brand new and a hundred years old. That's the whole idea.
— scenes from our soft launch event —
Halloween at Sweet’s! Doors at 5. Dance with Souled Out and compete for $250, $150 & $100 costume prizes. Tickets $17.85.
Ring it in at Sweet’s — dance 2026 away.
Dates penciled — final lineup announced to the list first.
At the Newberry
Old Town's own brewery — soon to be brewing beer on the main floor of Sweet Caroline's at the New Berry Building.
Alesatian has been brewing on Loudoun Street since long before we got here. House lagers, hazies, and more — brewed upstairs on the main floor, served properly cold on the lower level at the Alesatian Brewing Tap House.
Sweet Caroline's is a restaurant, bar and live music venue in the historic Newberry Building in Old Town Winchester, Virginia. An open kitchen, a full bar and a live stage share one room, and the building also houses the Alesatian Brewing tap room.
Sweet Caroline's is at 145 N. Loudoun Street, Winchester, VA 22601, inside the Newberry Building on the Loudoun Street pedestrian mall in Old Town Winchester.
The stage is hosting live music and events now, and the full kitchen and bar are on the way. Regular hours will be announced soon on Instagram (@sweet_carolines26_) and Facebook.
Sweet Caroline's pours award-winning beer from Alesatian Brewing Company, the Old Town Winchester brewery that has its tap room in the Newberry Building. The bar also features bourbon and a wine list.
Yes. The stage was designed by musicians and showcases professional local and national artists. Upcoming shows include Souled Out at the Old Town Monster Mash on Halloween, October 31, 2026, and a New Year's Eve party.
The Old Town Monster Mash presented by Friends of Old Town on Halloween, Saturday, October 31, 2026 (doors 5 PM, 5–11 PM, Souled Out live, $250/$150/$100 costume prizes, tickets $17.85 on Eventbrite); and New Year's Eve on December 31, 2026.