Neighborhoods
Beverage director Ryan Lotz shares his perfect day in the South End, full of food, wine, shopping, and art.
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].
The South End’s story is one of growth and change. Its historic brownstones sit next to rising condos and limited affordable housing, and iconic family-run bars neighbor new, glitzy fine-dining concepts.
Running between Back Bay, Chinatown, and Roxbury, the South End started out as Native land before the European settlers arrived. At some point during Boston’s growth, the South End was a central, affordable option for the many immigrants that flocked to the city.
It was a safe haven for the LGBTQ+ community and home to artists in the 20th century. New England’s largest homeless shelter, Pine Street Inn, planted its roots here, as well as other advocacy groups and social service organizations.
And because of urban renewal and redlining, the South End is now a major example of gentrification and displacement in Boston. Those beautiful brownstones cost millions, its residents are mostly young, wealthy families, and the businesses sell pricey, trendy goods.
Despite those changes, the South End’s history is still visible.
The neighborhood is well known as gay-friendly, hosting the city’s Pride parade each year. You can dip into hundreds of art galleries along Harrison Avenue and Tremont Street.
It also remains a base for activist groups and nonprofits, like Pine Street Inn and its recent affordable housing redevelopments. Inquilinos Boricuas en Acción (IBA), a decades old non-profit in the South End dedicated to increasing social and economic mobility, is in the process of building a 26,000-square-foot community center for Latino arts and activism.
It’s also been the epicenter of Boston’s homelessness, mental health, and substance abuse crises at Massachusetts Avenue and Melnea Cass Boulevard.
Its history and growth are complicated, to be sure. But possibly one bright spot in the South End is its support of local businesses, particularly restaurants.
“I really do love the way the South End has fostered independent businesses,” said Ryan Lotz, Mass. Restaurants United president and beverage director for Traveler Street Hospitality. “The South End is really one of those long-standing bastions of walkable neighborhoods with brick streets and shops you can stop in and restaurants you can have lunch or a glass of wine.”
Lotz doesn’t live in the South End, but he might as well be a resident, estimating that he spends 60 hours a week in the neighborhood away from his home in South Boston. All of the restaurants in Traveler Street Hospitality — Bar Mezzana, Shore Leave, No Relation, and Black Lamb — are located in the South End.
One of the biggest events in the neighborhood occurs in June, with Pride bringing out more than 1 million revelers. But Lotz said the neighborhood is a great winter alternative given its walkability, winter decorations, and of course, the dining scene.
We asked Lotz about what his perfect day in the South End would entail this winter, and here is what’s on the itinerary.
Morning | Afternoon | Evening | Map | Share your perfect day in Boston
Morning in the South End
Let’s face it: Winter is both New England’s longest season and its worst one. The bar, weather-wise, is low for a perfect day in the winter, but Lotz said the great thing about the South End is that there’s always something going on, even on a chilly day.
To make the day perfect, wear layers and a good pair of boots, in case there’s snow on the ground. Bring a scarf and hat just in case. But if it’s anything like the last several winter seasons, be prepared to carry your coat and winter accessories on days when it’s unseasonably warm.
Because Lotz works nights in the industry, his perfect day won’t start until 10 a.m. at the earliest.
That time of day and varying weather conditions make Flour Bakery + Cafe the perfect first stop. Joanne Chang’s beloved bakery has expanded to nine shops — a 10th store is on its way to Boston Common — but the award-winning chef got her start here at the South End location.
“Joanne Chang and Flour Bakery are [icons] in the city of Boston,” Lotz said.
He’s likely grabbing his favorite breakfast sandwich and a coffee to-go, but you also can’t go wrong with her famous sticky buns.
Next he’s taking a slow stroll through the South End’s many parks and gardens. Start at the one just across the street from Flour, the Rutland-Washington Community Garden.
Walk through a few more, and you’ll probably end up near one of the South End’s many small, independent businesses.
Looking for a new book? Try Parkside Bookshop, one of Boston’s newest bookstores that also hosts an array of events. The South End also has More Than Words, a non-profit that teaches at-risk youth business skills by having them run the bookstore and gift shop.
Buy a new sweater from SAULT New England, one of Lotz’s favorite clothing stores. Grab a bottle of wine for that New Year’s Eve party from either BRIX Wine Shop or the newer Neighborhood Wines.
Afternoon in the South End
All that shopping has worked up Lotz’s appetite, so he’s off to Kava Neo-Taverna for lunch that’s only offered on Friday through Sunday. This Mazi Food Group spot uses ingredients imported directly from the Mediterranean to build its Greek menu, plus it has hard-to-find Greek wines available by the glass and bottle.
Lotz said lunch is a great time to go since this beloved place is usually booked for dinner.
“Their zucchini chips are one of my favorite dishes in the city,” Lotz said.
Be sure to take in Union Park, a park nestled between a row of brownstones that go all out for holidays like Halloween and Christmas.
Lotz’s other lunch picks include South End Buttery, Picco for Lotz’s favorite Caesar salad, and Black Lamb for $2 oysters.
When you’re in the South End, it’s the best time to take advantage of all the surrounding art that the neighborhood has to offer. So Lotz is headed to the Cyclorama at the Boston Center for the Arts. Housed in a 140-year-old building, the venue hosts events like the Boston Art Book Fair, Taste of the South End, and the performance event #HellaBlack.
“People should take a look at what’s going on because they put on such interesting exhibitions that rotate throughout the year,” Lotz said.
For more art, peruse the 20-plus artist galleries at SoWa, where you can snag local art that was likely made in the nearby SoWa artist studios. Or catch a play at the Huntington Calderwood theater.
Taking in all that art calls for a stop at one of the country’s best cheese shops, according to Lotz.
Formaggio Kitchen has three Greater Boston locations, two in Cambridge and one in the South End. This cheesemonger has, well, cheese, but customers can also go there to grab a bottle of wine, craft beer, other gourmet groceries, prepared foods, and there’s even an option to join their monthly cheese club.
Lotz’s recommendation: You can’t go wrong with trying anything here, whether it’s a piece of cheese, their Italian sandwich, a mustard, or a canned spritz.
Evening in the South End
A harder decision to make in the South End is dinner, a time of day when the neighborhood’s celebrated dining scene comes alive.
And deciding on where to go for supper possibly becomes harder every year, as new places continue to open up in the neighborhood. Take Kaia, for example, the newest Greek restaurant from the award-winning team behind Krasi and Bar Vlaha.
Then there’s Baleia, one of the city’s most exciting new restaurants that describes itself as a “love letter to Portugal.”
“The chef that’s doing food there is just in love with Portuguese food,” Lotz said. “I love their Piri Piri chicken — I get it like twice a month.”
Lotz had to give a shoutout to one of his restaurants, Bar Mezzana, which has been serving crudo and pasta to the South End since 2016.
Add a bottle of wine from their “almost entirely Italian wine list,” and you’ve got yourself a meal, Lotz said.
Ending the day with some libations is also easier to do in this Boston neighborhood than most. The South End is a lively destination for young professionals, no matter their taste in drinks.
Want a modern tiki bar experience? Lotz recommends Shore Leave. Grab a seat during Halloween or the winter holidays for the bar’s transformation into a holiday-themed pop-up.
The South End is home to a bar that claims the status of the city’s oldest Irish pub, J.J. Foley’s Cafe. It’s worth noting that this bar has been owned by the same family since 1909, when it opened.
“They pour a fantastic Guinness,” Lotz said. “It’s one of my favorite stops.”
For some live music with your drink, the iconic and historic Wally’s Cafe Jazz Club is the place to be. Local musicians and Berklee students play there seven days a week, but it’s also hosted jazz legends like Charlie Parker and Duke Ellington.
So maybe you can’t fit all of Lotz’s recommendations into one perfect day, but that’s just an excuse to find yourself back in the South End.
“There is just a sense of the South End being this microcosm where you almost don’t even need to leave it,” Lotz said. “It’s just a really lovely, easy place to exist in a big city.”
Map of the perfect day in the South End
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