The Jimmy Expands to Winston-Salem With New Grounds Location

The Jimmy will bring wood-fired pizzas, chophouse-style dishes and rooftop dining to Winston-Salem’s new mixed-use district

Charmain Pieterse News Writer
The Jimmy will bring wood-fired pizzas, Mediterranean and Italian fare, and rooftop dining to The Grounds in Winston-Salem (Image credit: The Jimmy)

The Jimmy is expanding to Winston-Salem with a new restaurant at 519 Deacon Blvd, joining The Grounds’ 100-acre mixed-use development. The restaurant and bar, from the team behind Rooster’s and Copain, will bring an expanded Mediterranean and Italian offering to The Grounds’ Retail & Dining Village, according to The Go To Winston-Salem.

The Winston-Salem location is expected to feature wood-fired pizzas alongside a chophouse-style menu, with rooftop space overlooking the district. The Grounds is being developed as a destination combining restaurants, retail, student housing, trails and residential offerings, with its Retail & Dining Village designed around patios, rooftops and outdoor gathering spaces.

The Jimmy’s existing menu highlights Italian-inspired dishes alongside Mediterranean influences, with options ranging from wood-fired pizzas and pasta to steaks, seafood and seasonal selections. The restaurant also offers cocktails and other drinks to complement its full-service dining experience, according to their website.

The new Winston-Salem restaurant will add another location for The Jimmy as the concept grows beyond its existing market. The restaurant is part of the first group of five retailers announced for The Grounds, alongside The Fieldhouse Tavern, Bagels & Co., TREMBLE and Allegacy Financial.

More tenants are expected to be announced for The Grounds by early 2027, adding further restaurants, retail and gathering spaces to the developing Winston-Salem district.

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I am a South Africa-based reporter for WhatNow Media Group covering restaurant and retail openings in Charlotte and Nashville. I hold a Bachelor’s degree in Languages, specializing in Journalism, from the University of Pretoria, and bring 20 years of industry experience to my work. My reporting focuses on pre-opening developments, new concepts, and the people behind the businesses shaping local communities. I enjoy connecting with hospitality and retail professionals, learning their stories and sharing their insights, passions, and growth with readers. When I’m not reporting, I’m always interested in discovering the next business, concept, or story worth telling.
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