
A 6,000-square-foot-space with a capacity of 216. Cassidy McNeeley photo
Drop the “Dot” and the long rides downtown, and you have The Chester Tavern – a sophisticated but approachable dining experience rooted in fun set to open on Dorchester Avenue in Savin Hill this week.
Brought to you by Hawkeye Hospitality, The Chester hopes to bring a new dining option— including Sunday brunch, mid-week lunch, or late night options on the weekends— to the avenue on the ground level of a newly built, 21-unit condo complex a half-block south of Savin Hill Avenue.
“What we wanted to do with this project is create a really fun and exciting vibe and restaurant where you could come and not break the bank and have an affordable experience, but also have some high-end food and beverages,” said owner Dylan Welsh.
“We certainly don’t want a place that’s just a Friday destination or just a Sunday fun day thing. If you’re looking to have a good time and you want to be social and you want to have a great kind of fun experience Monday through Sunday, that’s what we’re trying to achieve.”
Welsh, who opened his first restaurant in 2011, and his team at Hawkeye are looking to build on the success of their other eateries, among them Five Horses Tavern outposts in Somerville and in Boston’s South End, the Elm Street Taproom in Somerville’s Davis Square, and the Garrison House in Brookline Village.
Now it’s Dorchester’s turn. But this time the team is bigger than before.

“This project’s unique, because Hawkeye Hospitality is getting an opportunity to kind of partner with other restaurateurs in the area. Some of my partners in this project are involved in the Playwright and Broadway in Southie,” Welsh told The Reporter during a tour of the tavern last Friday afternoon (May 8).
“It’s been great,” he said, “because with other restaurant minds at work, you get a better product. We’re all very creative people, but when you have really experienced restaurant people in the same room, – we have six restaurants, they have a bunch of restaurants – good things happen.”
The Chester is big: A 6,000-square-foot-space with a capacity of 216. The focal point of the dining room is something Welsh has not done before: a 47-seat, 360-degree-access bar.
“My partners come from bigger places, and they historically do big bars. It’s been my first project doing it,” he said about the bar, with its 24 draft lines, 9 TVs, and a pair of retractable screens. “I’m excited about it because the bar is a centerpiece. It’s a place for people to be social and see each other.”
The rest of the room features a mixture of high-tops and booths beneath an industrial-style ceiling, low-hanging lights, and silhouettes evoking the 1930s-40s jazz and big band era.
“The creative process for this project has been flowing and flowing. We kind of approached not being pigeonholed into an original design, but evolving throughout the process,” said Welsh. The same can be said for the tavern’s name, which has created buzz up and down Dot Ave.
“That was an evolution, too. The original name is not what we landed on. We went back and forth. “The Dorchester” was one option tossed around, “Five Horses” was tossed around, and we landed on The Chester.”
He added, “We want to be approachable, we want it to roll off the tongue. We want people to be sitting on their couches on a Friday night, being like, ‘Where do you want to go tonight?’ And ‘Let’s go to Chester’ and have that mean let’s go have some fun, let’s go be social, let’s go have some good food and drinks, and just really enjoy each other’s company.
“The space is designed to make you feel like you’re dining in an elevated experience, whether dressed up or down. “Sometimes you’re dressed up, sometimes you’re not. You’re not going to feel uncomfortable if you come in wearing a Patriots jersey.”
The plan is to open this week for dinner (keep an eye on their Instagram for specifics), with brunch and lunch service to be rolled out later.
“For the first week, we’re not doing lunch,” he said. “But we’re going to start lunch within the second week of opening, and will be open 11:30 a.m. to 1 a.m. We’re going to start brunch in two to three weeks. It’s going to be 10 a.m. to one o’clock on those nights.”
With the weather finally warming up, diners and drinkers can enjoy the bars’ year-round dining area enclosed within three large garage doors.
“You can’t even consider it a patio,” said Welsh. “It’s like exterior dining. It’s heated, covered, these doors are going to go up, and they’re going to stay up 24/7. That’s our dining room. It’s nice to have a huge storefront that’s able to open.”

Dylan Welsh, The Chester’s owner, with head chef Anne Moynihan. Cassidy McNeeley photo
The menu is billed as modern American tavern fare.
“Our chef Anne [Moynihan] is from our group; she’s been working with us for about four years now,” Welsh said. “The best chef I’ve ever worked with. I mean, the most level-headed, the most even-keeled personality that just carries herself with so much experience. We’re also sharing menu items and culinary experience amongst all these restaurants. We are working with the Broadway and Playwright and some of the things that they’re doing so that we can kind of deliver the most balanced, well-rounded menu we can.”
Starters include Buffalo Chicken Rangoons, Smoke House Sliders, and Tuna Tartare. For meals, you can choose between greens and bowls like the Smoky Southwest Steak Salad, handhelds like the Crispy Chicken Sandwich, and main entrees like the Ragin’ Cajun Pasta.
Chester fare also includes pizza and a bit of blast from the past with Moynihan’s take on pizza rolls.
“Our greens and bowls bring a lot of flavor and creativity, but you leave feeling like you don’t need to go for a run,” joked Welsh. “We have an awesome pizza oven back there, too. We’re cooking some really nice pizzas, and we’re doing these pizza rolls. It’s like a mini calzone that’s sliced four times. It’s perfect for, like, a table of four to split while you’re waiting.”
He continued: “I enjoy restaurants where I go out for special occasions and stuff like that. [But] you’re not going to walk out of here thinking, ‘Oh, I can’t come back for a couple of weeks.’ I think that’s important. This is designed to be somewhere someone can feel comfortable visiting many times throughout the week.”

Each menu item can be paired with a wide array of beverages. Whether a beer on draft, a canned seltzer, a pitcher of sangria, or even a scorpion bowl, there sems to be just about something for everyone.
There are plenty of cocktails and mocktails available, too. Options include the Chocolate Martini with vanilla vodka, chocolate liquor, and more chocolate; the Golden Ticket, an Evan Williams bourbon-based drink with Montenegro, honey, and lemon; and The Spicy One with spicy tequila, pamplemousse, grapefruit, and lime.
The neighborhood “is in need of more places like this,” said Welsh. “There are a lot of great places like Lucy’s, and in that area, The Bowery, Chubbs, all those great places, but you can’t walk there. From there to Boston, you have this area.
“We view it as an upcoming area that has a lot of diversity, a lot of young people. We felt the need for more restaurants. I try to be thoughtful in my neighborhood selections. All our places are in neighborhoods. That’s one thing we have all in common, all the partners in this project, we’re neighborhood guys.
We enjoy the dynamic that comes with it. The neighborhood, the people who live in the area, they’re very important to what we do.”
Welsh said that many neighbors have applied to work at The Chester, which is hiring online for both front and back of house positions. The more positions filled, the sooner they can open for brunch, lunch, dinner, and late-night service.
“There are so many other good things going on in Dorchester, but this place needed more,” insisted Welsh. “This area has some room for us to grow in. We want to be an amenity. I want to be a positive amenity.”
For updates on the Chester’s opening, visit Instagram.com/chestertavern.

A view of the exterior of The Chester. Cassidy McNeeley photo


