Three Sheets to the Wind bandmember opening new restaurant in Ashland

ash olive interior Cropped scaled

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 jessica brooks

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. 

ash olive interior Cropped scaled

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 jessica brooks

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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Sara Stern
Sara Stern
2 months ago

Congratulations! Always fun to have a new restaurant in the area. I hope you will offer some gluten free options for those with celiac disease. We always feel like second class citizens at restaurants because the gluten free options are an afterthought – like “sure, you can have a salad”. No thought to cross-contamination, gluten free bread or desserts. Hope we can look forward to dining at Ash & Olive!

Eden Fowler
Eden Fowler
2 months ago

What a beautiful space and exciting concept. I love the house cocktail program and the focus on fresh ingredients. Looking forward to taking the short train ride from Richmond to Ashland and eating here soon!!

Shannon McMillan
Shannon McMillan
2 months ago

Cannot wait for opening day, Gregg!!! So excited for this new venture and the vibe you’ll add to downtown Ashland!

Leon Harvey
Leon Harvey
2 months ago

Congrats…can’t wait to check it out!

Philippe Herndon
Philippe Herndon
2 months ago

I’m in my fourth decade of knowing Gregg, and he and Jess know food and hospitality. If aliens arrived on our planet and the fate of humanity depended on choosing our champion for a one on one fistfight, I’d time travel to borrow Mike Tyson from the night of the Spinks fight. But if our fate depended on us hosting the alien envoy for a fine event and meal, we’d do well to just let Gregg and Jess put a nice team and place together, and it sounds like that’s what they’ve done here. Kudos.

Chrissy Trower
Chrissy Trower
2 months ago

I miss you so very much!

Bill Zabka
Bill Zabka
2 months ago

This may be the single best comment in the history of Bizsense.

Alex Rickers
Alex Rickers
2 months ago

We CANNOT wait to frequent Ash and Olive! All the food and drinks sound amazing and the space is stunning!

Jimmy Zednik
Jimmy Zednik
2 months ago

Thrilled to see this addition to an exciting downtown Ashland scene that is blossoming into a great centerpiece for the local community as well as a destination for visitors from near and far to enjoy! Gregg Brooks has been a great friend as well as a bandmate and restaurant coworker over the years and I am super excited to see what he and Jessica have in store for this new project! Gregg’s passion and decades of experience in some of the best Richmond restaurants, along with his joy for adventurous culinary creations in his home kitchen set him on a… Read more »

Angi Baber
Angi Baber
2 months ago

This rocks!! So excited for y’all and for us! Can’t wait to try it out and have another spot where I can get delicious gluten free food and bevs

Kate Van Graafeiland
Kate Van Graafeiland
2 months ago

Really hopeful that they will label their menu for any items made with no gluten-containing ingredients 🤞

Kelly Jones
Kelly Jones
2 months ago

WHY would you open a place that sells beer and wine across the street from the Caboose?! We’re a small town and we want to support all the family owned businesses here. Why compete with an already existing, beloved business. Offer something different and you will find a loyal following. I wish you luck but really wish you weren’t adding competition to our lovely little town.

Bill Zabka
Bill Zabka
2 months ago

I don’t think the town of Ashland has any idea what these two are going to bring to the growing and thriving downtown community. Passion and experience are the drivers here, and it will be amazing to see this concept come together to give the people a truly unique dining environment.

catherine froman
catherine froman
2 months ago
Reply to  Bill Zabka

I’m excited to have new venue and exciting options!
Throw in some local Belle Isle libations and it will be perfect!