Boston Neighborhood Spotlight: Everything To Know About Fenway-Kenmore

Boston’s Fenway-Kenmore neighborhood is more than baseball
Boston’s Fenway-Kenmore neighborhood is more than baseball | © Della Huff / Alamy Stock Photo
Dana Forsythe

It’s fair if you simply think “Red Sox” when you hear the name “Fenway” in Boston, but the small neighborhood of the same name located just west of Downtown is so much more than a place to catch a baseball game.

Yes, Fenway Park is a huge draw for the Fenway neighborhood – attracting about 35,000 people for each of the Red Sox’s 82 home games – but the character of the area is far more nuanced. Amid the busy crowds of sports fans and swarms of university students, you’ll also find peaceful trails throughout quiet parks, museums, academic institutions and restaurants with high-end cuisine. Additionally, in the past 10 years, the neighborhood has seen millions of dollars in new development, creating a hip, safe and fun place where students, medical professionals and baseball fans can all rub shoulders.

Fenway Park draws thousands of people to the Fenway neighborhood

In addition to sports, burgers and bars, Fenway has a deeply rooted academic history with Simmons University, Boston University, Wentworth Institute of Technology and several more universities all lying within its borders. That’s not to mention the teaching schools inside the Longwood Medical area, home to a number of the world’s leading hospitals and research facilities.

The Fenway neighborhood is also home to the start of Frederick Law Olmsted’s massive park project in Boston, the Emerald Necklace, which is a chain of parks that look like they’re hanging from the “neck” of the Boston peninsula. Formerly swampland, the area has come a long way over the past 100-plus years and emerged as a unique intersection of city life, academia, sports and culture.

Kenmore and the Esplanade: Where old meets new

The Esplanade, one of Boston’s best assets, runs east to west from Science Park towards Allston along the Charles River. Created in the 1930s, it’s a long park of trails and trees and offers some of the best views of Cambridge and Boston. Even though the stretch of the Esplanade that runs through Fenway is situated on the backside of Boston University, the area is a hotspot for joggers, sunbathers, yogis, sailors and kayakers. Also, you’ll often find hundreds if not thousands of students walking along the paths to and from class.

While there are a few residential structures tucked in between BU housing and class buildings, Kenmore is now mostly home to students and centers around tourism. Some of the longer-standing shops are nestled between the residences.

Boston’s Fenway-Kenmore neighborhood is popular with tourists

Sugar Daddy’s Smoke Shop has been one of the anchor businesses in Kenmore Square since opening in 1996. With marijuana legalized in 2016, owner Bernard Henson said the store has been able to adopt new options in the market as well as maintaining a solid relationship with its customers.

“The Kenmore neighborhood has served as a gateway to the university area as well, and full-time residents tend to be a mix of recent grads and professionals,” Henson says. “The biggest change in the area has been the development of the Fenway side of the Fenway-Kenmore neighborhood.” Kenmore Square meets up with Fenway Park just two blocks down Brookline Avenue. The area immediately surrounding the ballpark and just south of it along Boylston Street has seen the most development.

“Prior to all the new construction, there wasn’t nearly as much as there is now. The dynamic shifted towards that new area,” Henson adds. “Kenmore Square is currently undergoing a transition as well. Mostly due to plans for another reconfiguration. We’ll have to see how it plays out in the coming years. You could talk about the real shift coming 20 years ago when the Hotel Commonwealth was built and changed the landscape initially, pushing out originals like Rathskellers and Deli Haus.”

Still, there are mainstays as well as newer additions that have helped keep Kenmore interesting and vibrant. Since it opened in 2005 in the husk of The Rat, Eastern Standard has been the dining anchor of the square. Food bloggers recommend favorites such as the butterscotch bread pudding and The Blueberry Thrill cocktail. Joining ES, the popular Island Creek Oyster Bar was opened by the same group in 2010.

If you’re looking for something less fancy, there are plenty of other options, including Pho Common, Fin’s and UBurger. If you’re looking for a quality pint and a game of pool or darts, there’s no better place to go than Cornwall’s, which opened 1973; it offers a full lunch and dinner menu.

In the Kenmore neighborhood since 1978, Nuggets Records is one of a few independent record stores. Nuggets owner Stuart Freedman started working at the store when he was still a student. Inside you can find new-old T-shirts promoting The Rat and records signed to the then-owner by the likes of Boz Scaggs and Willie Nelson. There are also bins of CDs, records, tapes and magazines to search through and an eclectic mix of tunes spinning upon every visit.

Beyond baseball

What can you write about Fenway Park, Boston’s biggest landmark and home to the Red Sox since 1912, that hasn’t been written already? The oldest baseball park in America is still a huge draw for tourists and baseball fans alike, but changes are coming. When Bruce Springsteen played the first show at Fenway Park in 2003, it was the start of something that is just now being realized. The Red Sox have plans to redevelop the small parcel of land on the corner of Ipswich Street and Lansdowne Street, pitching a 5,400-person theater. While the plans have yet to be finalized, the new development could be up as early as 2021.

Fenway Park opened in 1912

Aside from the Seaport, the back end of Fenway has seen the most development in Boston over the past few years. No small part of that has been thanks to Samuels & Associates, who, since 2004, have built three residential towers in the neighborhood. The towers feature landscaped terraces, rooftop decks and ground-floor retail space. The Verb Hotel and attached sushi restaurant and cocktail lounge, Hojoko, are perfect examples of the developer’s choices in selecting anchor businesses to reflect the new vibe of Fenway. Other restaurants include vegan hotspot by CHLOE, Eventide Fenway, Sweet Cheeks and Tiger Mama.

Inside Hojoko, you’ll get an immediate ’70s cocktail-lounge vibe. From the tiki drinks to the Hawaiian decor, the restaurant plays up its symbiotic relationship with the attached Verb Hotel and runs events such as vinyl nights, karaoke and dance nights. Developers renovated an old Howard Johnson hotel in 2014 and created The Verb, a restored mid-century classic that offers 93 guest rooms, each complete with a mini-fridge, views of the pool and a record player. At the front desk, visitors can even leaf through a collection of records to take up to their rooms.

Recently, Samuels has begun wrapping up its biggest project to date in Fenway. The Landmark Center, formerly the site of a Sears distribution center, is now open as 401 Park. The massive, 1-million-square-foot (92,903-square-metre) structure built in 1928 at the corner of Park Drive and Brookline Avenue cost an estimated $650 million to redevelop and includes hundreds of housing units, office space and the enormous Time Out Boston Market.

Created in 2014 by João Cepeda, then Portugal’s Time Out editorial director, the Time Out Market was designed to gather the city’s best local food and culture. The idea has since spread to cities such as New York and Miami. Inside Fenway’s largest indoor space, you can now find offerings from 15 restaurants operated by Boston chefs such as Michael Schlow and Nancy Cushman, two full-service bars, a demonstration kitchen and 650 communal seats.

Outside, the oddly shaped parking lot has been replaced with some new green space and the large-scale outdoor installation Grouping of Works from Fountain by contemporary artist Nicole Eisenman.

Recreation and research

When Frederick Law Olmsted first began development of the park system in Boston, he started in the Back Bay and Fenway areas. Olmstead transformed the region from swampland into usable plots by carving a salt marsh into the boggy area of the Fenway and rerouting the sewers from the Muddy River into the Charles with a series of floodgates.

Today, in the Back Bay Fens, you can walk through the fragrant James P Kelleher Rose Garden or stroll through the mini-plots of community gardens in the Fenway Garden Society. You can also try your hand or sit on the sidelines of a local basketball game in the central courts or watch athletes train along the track and field portion of the park. Farther towards Brookline, the park curves into the Riverway section, offering paved roads and dirt trails on either side of a small river, full of beautiful stone bridges throughout.

Back Bay Fens is a lush urban parkland

Originally filled in to make way for housing, the area surrounding the Emerald Necklace parks quickly evolved into a place of higher learning as colleges and universities sprung up in the early 1900s. Over a century later, the area is still heavily populated with educational institutions, including the Boston Symphony Hall, Northeastern University and MassArt, to name a few. Fenway is also home to the Boston Latin School – America’s first public school.

Accordingly, you’ll find a ton of students in this area. With Longwood Medical just down the road, medical professionals and post-grads are a common sight as well. Thankfully, this area is connected by the Green Line, which runs from Huntington out west towards Route 9. Along the way, you’ll see a cluster of college-centric coffee houses, restaurants and supply shops.

If you’re an art lover, there’s no better place for you in Boston than Fenway. Within a mile walk, you’ll be able to visit the Museum of Fine Arts, Boston and the Isabella Stewart Gardner Museum’s famous collection, which includes works by Michelangelo, Raphael and Rembrandt, among others.

Whether you’re looking for art, a picturesque stroll, a sports game, great eats or some time in a garden, Fenway has you covered.

1. The Verb Hotel

Boutique Hotel

The Verb Hotel
Courtesy of The Verb Hotel / Expedia

Stepping into The Verb Hotel is like entering a music history museum. Opening in 2014, it’s the perfect accommodation for those who love rock ‘n’ roll.

2. Hojoko

Restaurant, Japanese

The Verb’s on-site restaurant, Hojoko, features an incredible line-up of Asian-inspired dishes, including izakaya-inspired snacks such as “kimcheezy” fries topped with dashi-queso sauce and Hojoko kimchi, and “hamachos” with torched hamachi on dusted corn tortilla chips and avocado crema.

3. Tiger Mama

Restaurant, Asian

Tiger Mama, Boston, MA.
Courtesy of Tiger Mama

Nestled in the heart of the Fenway neighborhood, Tiger Mama is the creation of chef Tiffani Faison. It features a menu of Southeast-Asian-inspired eats and fruity tiki cocktails by beverage director Brian Callahan.

4. Eventide Fenway

Restaurant, Seafood

If you’re craving oysters and brown-butter lobster rolls, Eventide Fenway is the place to go. It’s a short walk from Fenway Park.

5. Island Creek Oyster Bar

Restaurant, Bar, Seafood

Island Creek Oyster Bar is open for lunch and dinner seven days a week plus weekend brunch. As its name suggests, Island Creek serves the freshest oysters, melt-in-your-mouth lobsters rolls and many other dishes – with or without seafood.

6. Eastern Standard

Cocktail Bar, Restaurant, American, Vegetarian, Vegan

Eastern Standard is an American brasserie inspired by not only French cuisine but also American fare. It also serves up craft cocktails that rotate with the seasons.

7. Cornwall’s

Bar, Pub, Pub Grub

Cornwall’s is a British-style pub that opened in Kenmore Square in the early ’70s and is something of an institution in the Fenway neighborhood. Come here for pool, darts, board games, beer and a full dining menu.

8. Museum of Fine Arts Boston


Museum Of Fine Arts, Boston, Massachusetts
© Universal Images Group North America LLC / Alamy Stock Photo
Museum-lovers will enjoy spending a few hours at the Museum of Fine Arts Boston (MFA) on Huntington Avenue. As the fourth largest museum in the United States, it houses almost 500,000 pieces of art in its permanent collection and also hosts visiting exhibitions.

9. Isabella Stewart Gardner Museum

Building, Museum

Boston Massachusetts, Isabella Stewart Gardner Museum, Boston Massachusetts, Renzo Piano addition, 2011, 2012,
© Stillman Rogers / Alamy Stock Photo
Housing artworks from Medieval Europe, Asia, Renaissance Italy and many other places, the Isabella Stewart Gardner Museum resembles a 15th-century Venetian palace, complete with a lovely courtyard. It also has a Renzo Piano-designed addition that showcases contemporary art.

10. Fenway Park

Stadium, Park

Fenway Park is the home of the Boston Red Sox baseball team
© Paule Saviano / Alamy Stock Photo
Fenway Park is the oldest operated baseball park in the USA, and attending a game is an iconic Boston experience. The park also offers tours.

11. Sugar Daddy’s Smoke Shop


Established in 1996, Sugar Daddy’s offers fun smoking trinkets and is expanding with legal marijuana options, too. The location in Kenmore Square offers access to many surrounding businesses and restaurants.

12. Nuggets Records


This vintage music shop is full of records, CDs, cassettes, VHS tapes, books, posters and more. You can also sell or trade older items you no longer want.

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