Old Town Winchester · VA
est. two thousand twenty-six
Restaurant · Bar · Stage

Sweet Caroline's

at the Newberry Building

Housing Alesatian + Tap Room

More to Come
peek inside

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.

Hand Crafting

A little of everything

№ 01
✤

The Kitchen

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 --

№ 02
❦

The Bar & Brewery

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 --

№ 03
♪

The Stage

Designed by musicians, for music — a room that sounds as good as it feels, showcasing professional local and national artists.
-- HAPPENING NOW --

№ 04
✦

The Room

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 --

The historic Newberry Building at 145 N. Loudoun Street in Old Town Winchester, VA, home of Sweet Caroline's restaurant, bar and live music venue
The home

Inside the Newberry Building

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.

145 N. Loudoun Street · Winchester · Virginia
On the calendar

Upcoming happenings

31 Oct

The Old Town Monster Mash · Friends of Old Town

Halloween at Sweet’s! Doors at 5. Dance with Souled Out and compete for $250, $150 & $100 costume prizes. Tickets $17.85.

Get Tickets →
31 Dec

New Year’s Eve

Ring it in at Sweet’s — dance 2026 away.

Live Music

Dates penciled — final lineup announced to the list first.

The Alesatian Brewing taproom downstairs at Sweet Caroline's, Newberry Building, Old Town Winchester VA

At the Newberry

Alesatian Brewing

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.

23 N. Loudoun St. Winchester, VA

Visit Alesatian →

Good to know

Questions, answered

What is Sweet Caroline's?

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.

Where is Sweet Caroline's located?

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.

Is Sweet Caroline's open?

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.

What beer does Sweet Caroline's serve?

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.

Does Sweet Caroline's have live music?

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.

What events are coming up at Sweet Caroline's?

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.