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Band member of Three Sheets to the Wind opens new restaurant in Ashland


Band member of Three Sheets to the Wind opens new restaurant in Ashland

Ash Olive Interior Cropped scaled

The 3,200 square meter area offers space for about 65 people.

A new Mediterranean restaurant is set to open on Ashland’s Main Street.

Ash & Olive is preparing to open at 107 S. Railroad Ave. in downtown.

The new restaurant takes over the former event rooms of the adjacent Cross Brothers grocery store.

Ash & Olive is the brainchild of Jessica and Gregg Brooks. Jessica is a long-time amateur cook with a background in corporate communications, while Gregg has worked in the wine, spirits and hospitality industries, as well as being a touring musician. His latest group, the yacht rock cover band Three Sheets to the Wind, launched a Steely Dan-inspired canned wine line, Steely Can Wine in 2022.

Gregg Jessica Brooks

Gregg and Jessica Brooks (Courtesy of Georgia Brooks)

The couple met at the former Arts District restaurant Comfort about ten years ago and discovered their love of food. Since then, the Brookses have married and are holding on to their dream of one day opening a restaurant.

“It was always a pipe dream,” said Gregg Brooks. “We had a concept on paper and kept bouncing ideas around.”

They started looking for a place in the region about a year ago when they heard about Chris Stem, who Purchased and rebuilt by Cross Brothers in 2018Stem offered them the grocer’s event space along Railroad Avenue.

“We had just realized how much growth was happening within a five-mile radius of the area and what an absolutely unique charm this environment had,” said Jessica Brooks.

“We met other business owners in town and learned that they had a real interest in bringing something different and new to the space. It seemed like all signs pointed to this being something we should make happen.”

They are now converting the 3,200-square-foot space into Ash & Olive. The restaurant’s menu will be inspired by Italian, Spanish and other Mediterranean cuisines, the Brookses said. They are installing a new brick oven in the space, which will be used to prepare most of Ash & Olive’s dishes.

“We will offer artisanal pizza and sandwiches and there will be no fryer. This forces us to use as many fresh ingredients as possible,” said Gregg Brooks, stressing that the restaurant will serve panuozzo sandwiches, a type of Italian sandwich whose bread resembles pizza dough.

Ash & Olive’s menu also includes steaks with fries, sausages and various salads, as well as gelato for dessert. There will also be a bar with in-house cocktail programs and a variety of wines, including some Steely Can varieties.

“We want to have something a little more fancy and cooler to go with the wine and cocktails,” said Gregg Brooks.

Ash & Olive will operate on a counter service model and will also offer prepared meals and wine and beer to go.

The Brookses said the space is more or less turnkey and they are in the process of finishing up work as they hope to open by the end of the summer. Jessica will stay at her day job and Gregg plans to run the restaurant full-time while still working part-time at Ashland’s Wine & Beer Supply. He will also continue with Three Sheets to the Wind, where he plays drums and sings.

Ash & Olive will be open daily from about 9 a.m. to 8 p.m., with longer hours on weekends. The Brookses said they also plan to offer brunch on the weekends.

Another new Italian-inspired restaurant Ashland is home to Il Forno Bar & Grill, which opened last month at 435 England St.

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