Neighborhoods

Billy Moran, general manager of Cornwall’s, takes us through his perfect night in Boston’s Fenway-Kenmore neighborhood.

In Boston.com’s Perfect Day series, we’re talking to a local expert in each of Boston’s 23 neighborhoods about how they’d spend their perfect day. See what makes this city so special to your neighbors, and share your perfect day with us at [email protected].

Fenway-Kenmore is full of cultural institutions, making the neighborhood a world-famous attraction for visitors near and far. 

In the late 1800s, a downtown fire led to local institutions looking to the open space in Fenway-Kenmore and Back Bay as a place to rebuild. The neighborhood then became home to Fenway Park, the Museum of Fine Arts, Symphony Hall, and the Citgo sign.

But before a historic baseball stadium, townhouses, and cultural centers popped up, it was just marshland. Fenway-Kenmore would see history repeat itself a few times, going from periods of vast development to “seedy” eras and back.

Once a spot for local bands to play their music in smaller dives, like at the Rathskeller, now it hosts some big-ticket musicians at its handful of music venues. Today, the neighborhood is also known from a restaurant and bar scene with a mix of cheap eats — though less of it these days — and fine dining. 

It’s that old and new balance that Billy Moran, general manager of Cornwall’s, loves about the neighborhood. Cornwall’s, a pub in Kenmore Square, isn’t immune to the shifting tides of the neighborhood, as it’s moved its popular bar several times.

“The old being the grit of the neighborhood of old Fenway, when there used to be a lot of live music. There’s still a lot of people that talk about the Rathskeller and a lot of the talent that started and came through this neighborhood. Post-COVID, it’s really Boston University and the Red Sox.”

Moran doesn’t live in Fenway-Kenmore, but he and his family have been part of the neighborhood since his uncle opened Cornwall’s in 1973. He’s also part of the Kenmore Business Association. 

That mix of old and new is certainly still present, with development plans this time promising lab and office space and residential properties.

And throughout Fenway-Kenmore’s history of development, one thing has been constant: It’s the collision of events, and all walks of life that pass through its streets, that keep this neighborhood buzzing. 

As baseball season ramps up, and spring events bring residents and visitors alike back outside, we asked Moran what a perfect night in Fenway-Kenmore looks like to him.

Afternoon: Fenway Franks and the Red Sox

Fenway-Kenmore wakes up in the afternoon, according to Moran, so it’s the perfect time to start his perfect night.

Moran said he’s most likely out and about in the neighborhood in April or May, when there’s a chance you can get all four seasons in one day, but he’s hoping for a 65-degree day during the afternoon. Perfect weather for a game at Fenway Park.

He’s starting his time in Fenway-Kenmore at his family’s place, Cornwall’s, with a California burger and a Guinness. 

“I’m going to a ball game — I’m getting a burger and a beer.”

Then, a house margarita from Loco Taqueria and Oyster Bar is in order just before a Red Sox game kicks off.

The perfect day for a game — as long as the weather cooperates — is a Saturday game at 4:10 p.m., Moran said. 

“You have the early afternoon, then catch the game, have dinner after, and jump out [of the city] at a decent hour,” Moran said. 

Inside the 112-year-old stadium, the oldest stadium in use by the MLB, Moran will probably order a Fenway Frank hot dog with mustard and relish.

“No ketchup — we don’t do that here,” Moran said. 

He’ll then make his way around the park and chat with Fenway employees, who he knows because they often find their way to Cornwall’s for a bite and beer after the game is over, Moran said.

Evening: Music and late-night bites

There’s an energy to Fenway-Kenmore after events let out, whether it’s a Red Sox game, a concert at House of Blues or MGM Music Hall, or a mix of festivities.

That’s what makes the evening the most lively time to be in Fenway-Kenmore, Moran said. 

“If you go to a show at MGM or House of Blues, to me it’s such a cool feeling when you walk out of either of those places on a nice night, and you look up and see the scoreboard at Fenway,” Moran said. “You really just walk out and feel charged by the energy.”

After the game, which hopefully ended in a Red Sox win for Moran, he heads over to Eastern Standard’s new location for one more snack and cocktail. Preferably their steak tartare and a Negroni.

What also stands out about Fenway-Kenmore in the evening, Moran said, is how late places stay open — for Boston standards, anyway. He mentioned Citizen Public House & Oyster Bar being a great destination for their whiskey menu and those in need of a late-night meal, with food available until 1:30 a.m. Monday through Saturday.

Moran also recommended the Trillium Brewery and Time Out Market, a food market in the Fenway, for the several diverse options of food for patrons to choose.

Morning: Brunch at the brasseries

Fenway-Kenmore isn’t really a morning spot to Moran, and there’s a couple of reasons for that.

Most events — besides the Boston Marathon, one of Moran’s favorite days in Fenway-Kenmore — start later in the day or evening. The earliest Red Sox games don’t even start until 1:30 p.m.

He also tends to work late at Cornwall’s, and doesn’t find himself out the next day after a shift.

But Moran points out that with the recent brasserie resurgence — the new Eastern Standard, Blue Ribbon Brasserie, and DW French — there is no shortage of brunch options in the area. 

“If I were going to do [brunch], I would go to either the Blue Ribbon Brasserie or [Eastern Standard] just because brasseries tend to do brunches as good as anyone.

If the day is nice enough for it, he may find himself walking along the Charles River Esplanade, which stretches for three miles from Downtown Boston and Back Bay to Fenway-Kenmore.

And admittedly, this next tip from Moran is not technically in Fenway-Kenmore. But part of a perfect day in Fenway-Kenmore means walking through its many green spaces to Back Bay. His go-to spot for breakfast is just beyond the Fenway-Kenmore borders at Cafe Sauvage, where he orders a simple meal: a breakfast sandwich and a coffee, black. 

Fenway-Kenmore is busy with tourists and locals for a reason — you can spend a whole day there easily.

The neighborhood, just like the rest of the city, was hit hard by COVID-19, particularly because business is so driven by events in Fenway-Kenmore, Moran said. And let’s face it: Boston’s weather isn’t always a great driver for getting people out.

But it was this year’s Marathon Monday — an unseasonably warm day perfect for spectators, not so much for the runners — when Moran once again felt that energy that has been part of Fenway-Kenmore for decades.

“It brought together all the different aspects of the neighborhood: people who have lived here for a very long time, people from Boston University, people going to the Red Sox game, and people just in town for the marathon.”

Find all of Billy Moran’s recommended spots and other places mentioned in the story below:

What does a perfect day in Boston look like to you?