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Here’s how to have the perfect night at Fenway-Kenmore

Neighborhoods

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

Fenway Park

Fans gather in front of Fenway Park before a home opener baseball game between the Boston Red Sox and the Baltimore Orioles, Tuesday, April 9, 2024, in Boston. Michael Dwyer/Associated Press

In Boston.com’s Perfect Day series, we talk with a local expert from each of Boston’s 23 neighborhoods about how they would spend their perfect day. Find out what makes this city so special to your neighbors and share your perfect day with us on (email protected).


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

In the late 1800s, a downtown fire caused local institutions to turn to the open spaces of Fenway-Kenmore and Back Bay as a place to rebuild. The neighborhood is then home to Fenway Park, the Museum of Fine Arts, Symphony Hall and the Citgo brand.

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But before the appearance of a historic baseball stadium, townhouses and cultural centers, it was just a swamp. Fenway-Kenmore would see history repeat itself repeatedly, moving from periods of vast development to “shabby” times and back again.

Once a place where local bands played their music in smaller venues, such as at the Rathskeller, it now hosts expensive musicians in its handful of live music venues. Today, the area is also known for its restaurants and bars offering a mix of cheap eats – although less so these days – and fine dining.

It’s this balance of old and new that Billy Moran, general manager of Cornwall’s, likes about the neighborhood. Cornwall’s, a pub in Kenmore Square, is not immune to the neighborhood’s changing tides, having moved its popular bar several times.

“The old one being the old Fenway area, back when there was a lot of live music. There are still a lot of people talking about the Rathskellers and a lot of talent that started and emerged in this area. Post-COVID is really Boston University and the Red Sox.

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

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

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

As baseball season ramps up and spring events bring residents and visitors outdoors again, we asked Moran what a perfect evening at 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 her perfect night.

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

He begins his stay in Fenway-Kenmore with his family, Cornwallwith a Californian burger and a Guinness.

“I go to a football game – I have a burger and a beer.”

Then a daisy house by Loco Taqueria and Oyster Bar is a must just before kickoff of a Red Sox game.

Fans fill the field level seats at Fenway Park for the Boston Red Sox home opener against the Baltimore Orioles. (Danielle Parhizkaran/Globe team)

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

“You have the early afternoon, then go to the game, have dinner afterward and get out (of town) at a decent hour,” Moran said.

Inside the 112-year-old stadium, the oldest stadium used by MLB, Moran will likely command a Fenway Frank mustard and relish hot dog.

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

He will then move around the park and chat with Fenway employees, whom he knows because they often go to Cornwall for a bite to eat and a beer after the game is over, Moran said.

Jose Magrass sells Fenway Franks before a Red Sox game against the Toronto Blue Jays at Fenway Park in Boston on Wednesday, July 6, 2011. (Yoon S. Byun/Globe Staff)

Evening: Music and late night bites

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

That’s what makes the evening the busiest time at Fenway-Kenmore, Moran said.

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

Steak tartare at Eastern Standard. (Nathan Klima/Boston Globe)

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

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

Moran also recommended Trillium Brewery and Time Out Market, a food market in Fenway, for the different food options available to customers.

Morning: Brasserie brunch

Fenway-Kenmore isn’t much of a morning spot in Moran, and there are a few reasons for that.

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

He also tends to work late at Cornwall and doesn’t show up the next day after a shift.

Runners flocked to Kenmore Square as they neared the finish line of the Boston Marathon. Dina Rudick/Boston Globe.

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

“If I had to do (brunch), I would either go to Blue Ribbon Brewery or (Eastern Standard) just because breweries tend to make brunches as good as anyone.

If the day permits, he might find himself walking along the Charles River Esplanade, which stretches three miles from downtown Boston and the Back Bay to Fenway-Kenmore.

And admittedly, this next tip from Moran isn’t technically at Fenway-Kenmore. But a perfect day in Fenway-Kenmore involves strolling through its many green spaces to Back Bay. His favorite breakfast spot is just beyond the Fenway-Kenmore borders at Café Sauvage, where he orders a simple meal: a breakfast sandwich and coffee, black.

Fenway-Kenmore is popular with tourists and locals for a reason: you can easily spend an entire day there.

The neighborhood, much like the rest of the city, has been hit hard by COVID-19, particularly because business is greatly boosted by events at Fenway-Kenmore, Moran said. And let’s be real: the weather in Boston isn’t always a good factor in getting people out.

But it was the Monday of this year’s marathon — an unseasonably warm day, perfect for spectators, not so much for runners — that Moran again felt that energy that has been a 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 who go to the Red Sox game and people just in town for the marathon.”

Find all the places recommended by Billy Moran and other places mentioned in the story below:


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