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 Loudoun Street in Old Town Winchester, VA, home of Sweet Caroline's restaurant and brewery
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 Loudoun Street · Winchester · Virginia
On the calendar

Opening happenings

3 July

First Friday · Gary Smallwood

Kick off the month with live music from Gary Smallwood.

Live Music
4 July

July 4th Blowout

Doors at noon. Souled Out takes the stage 6–9pm. Celebrate the 4th. Meet @ Sweet’s.

All Ages
Aug Date TBD

Oyster Fest at Sweet’s!

Oysters, Oysters, & more Oysters! More information coming soon.

All Ages
26 Sept

Oktober Festival

Doors at noon. Contests, performances & music all day — wear your favorite dirndl & lederhosen. Full schedule TBD.

All Ages
31 Oct

Halloween with Souled Out

The area’s favorite dance band brings the costume party. Meet @ Sweet’s.

Live Music
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

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