Three Sheets to the Wind bandmember opening new restaurant in Ashland

The 3,200-square-foot space has capacity for around 65. (Photos courtesy Georgia Brooks)

A new Mediterranean restaurant is set to pull into Ashland’s main drag. 

Ash & Olive is preparing to open at 107 S. Railroad Ave. in the town’s downtown area. 

The new restaurant is taking over what had been an event space for the adjacent Cross Brothers grocery store. 

Behind Ash & Olive is couple Jessica and Gregg Brooks. Jessica is a longtime home cook whose professional background is in corporate communications, while Gregg has worked in the wine, spirits and restaurant industries, and as a touring musician. His latest troupe, yacht rock cover band Three Sheets to the Wind, rolled out a Steely Dan-inspired canned wine line, Steely Can Wine in 2022.

Gregg and Jessica Brooks 

The pair met at the former Arts District restaurant Comfort about a decade ago and bonded over their love of food. Since then the Brookses have gotten married and held onto a dream of someday opening a restaurant. 

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

They began looking around the region for a space about a year ago when they heard from Chris Stem, who had bought and revamped Cross Brothers in 2018. Stem offered them the grocer’s event space along Railroad Avenue. 

“We’d just realized what growth was happening in a 5-mile radius in the area and the absolutely unique charm of that setting,” Jessica Brooks said.

“We met other business owners from the town and how they’ve had a real interest in having something different and new come to the space. It seemed like all signs were pointing to it being something we should make happen.”

They’re 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’re installing a new stone oven in the space that will cook the majority of Ash & Olive’s dishes. 

“We’ll have artisan pizzas and sandwiches, and there’ll be no fryer. That forces us to use as many fresh ingredients as possible,” Gregg Brooks said, emphasizing that the restaurant will serve panuozzo sandwiches, a type of Italian sandwich whose bread is akin to pizza dough. 

Ash & Olive’s menu also will include steak frites, charcuterie and a variety of salads, plus gelato for dessert. It’ll also have a bar with a house cocktail program and a variety of wines, including a few Steely Can selections. 

“We want to have some funkier and cooler stuff with the wine and cocktails,” Gregg Brooks said.

Ash & Olive will operate with a counter-service model and also have prepared foods and wine and beer for sale to-go.

The Brookses said the space was more or less turnkey and they’re finalizing the work on it now as they look to open by the end of the summer. Jessica will stay on at her day job, and Gregg is planning to run the restaurant full time while also working part-time at Ashland’s Wine & Beer Supply. He’ll also continue with Three Sheets to the Wind, where he plays drums and sings. 

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

Another new Italian-influenced restaurant in Ashland recently is Il Forno Bar & Grill, which opened last month at 435 England St. 

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