Boston is where I live, but the South End is home. If you visit Boston, you’ll understand this city is defined by its neighborhoods. Each have their own history, architecture and personality. The South End was one of America’s earliest large-scale residential developments and much of that pre- and post-Civil War architecture remains. A good example is Boston’s Union Park in the South End, which was built in the late 1850s.
In the first half of the 20th Century, the South End would become the home for many immigrant groups notably Greek, Lebanese, Africans, and Caribbean/West Indies. It also became home for many in the city’s Black population (e.g., 395-397 Massachusetts Ave was home to Martin Luther King Jr. in the early 1950s). In the early 1970s many artists and gay men moved here for the cheap rent. By then the neighborhood had a well-deserved seedy reputation and was afflicted by urban blight and crime. It wasn’t until the 1990s that Boston’s population started to rebound and places like the South End started to flourish again. That gentrification would also result in Boston’s gay population moving out to Dorchester, Jamaica Plain, Davis Square and elsewhere.
About The South End: The South End is a contradiction. It has some of the most affluent properties and toniest addresses in the city. Yet, it’s home to the city’s largest soup kitchen, Pine Street Inn, large public housing complexes, Boston’s safety net hospital Boston Medical Center and its neighboring Healthcare for the Homeless. Despite its affluence, these institutions (thankfully) aren’t going anywhere. It is this socio-economic mix that has saved the South End from becoming one-dimensional and gives it personality.
The South End is incredibly charming. Built on landfill in the mid-19th century as a residential district for Boston’s growing upper middle-class, hundreds of Victorian Bow Fronts were built and today it’s the largest enclave of urban Victorian residential architecture in the country. However, one of the most beautiful buildings in the South End isn’t Victorian, it’s Gothic Revival architecture. The Cathedral of the Holy Cross (est.1875) made from nearby Roxbury puddingstone and gray limestone stands in stark contrast to the Victorian and newer glass and steel residential buildings in the SoWa district of the South End. If you get a chance, look inside. The Cathedral was recently lovingly cleaned and restored and it is beautiful inside and out.
For more information about this beautiful neighborhood, I recommend reading the Boston’s South End: The Clash of Ideas in a Historic Neighborhood, by longtime South End resident, friend, and neighbor, Russ Lopez.
What to do in the South End: The South End is a picturesque, residential neighborhood with many parks to enjoy. If you spend any time here, you’ll likely find yourself walking through some of these green spaces. Some of our favorite parks are The Underground, Peter’s Park, Blackstone & Franklin Squares, and the Southwest Corridor, which divides the South End and Back Bay.
Aside from strolling through the parks and streets of the South End, I love the local theater companies that (when there isn’t a pandemic) perform at the Black Box Theater and Calderwood Pavilion. I think of the South End as a mini-theater district with The Huntington, SpeakEasy Stage and Company One all providing entertaining shows. Additionally, the First Friday of each month from 5-9PM is SoWa First Fridays where scores of art galleries and artisans open their studios to the public. The theater companies and First Fridays bring many people here for a fun date night or evening out with friends – especially when followed by drinks and dinner (but more about that later).
In addition to window shopping (there are many unique shops, complete listing here), enjoying the parks, or checking out the local arts scene, the South End hosts several markets and events. One of my favorites is the SoWa Open Market, which runs each Sunday (May thru October). It includes an artisan and farmer’s market, food trucks and a vintage market (this runs year round). There are also many interesting exhibits and events hosted at the BCA Cyclorama and at the new events and exhibition venue, The South End Power Station, but if all that sounds exhausting, don’t worry there are many places to relax.
Cafes in the South End: One of the things I love about this neighborhood is its many cafes and restaurants. Visitors may feel lost with very few national chains present (which by the way is a good thing), but it adds personality and allows local chains and sole proprietorships to thrive. In 2015, I wrote about the cafes in the South End. Since then a few have closed and a few have opened but the point is there are many places to meet a friend to enjoy a good cup of coffee and tempting treat or two. A favorite new coffee shop is MOD Espresso on Harrison Ave. If you’re in the n’hood, stop by and let me know what you think.
In 2014, I hosted a blind tasting to find out who made the best chocolate chip cookies in the South End. Should I write a new post about the many cafes or host another blind tasting to find the best chocolate chip cookies in the n’hood? Let me know your thoughts in the comments section.
Restaurants in the South End: Every restaurant I wrote about in my 2018 post, Best Places to Eat in the South End, have weathered the pandemic and remain open. If we can set the current pandemic aside, dining out in the South End has changed for the better in recent years. There are more affordable and casual dining options, and a greater variety of cuisines to enjoy.
The neighborhood has some of the best Italian and French restaurants Boston has to offer (too many to list). It also has great Asian restaurants (personal favorites include Elephant Walk and Myer’s + Chang), Eastern Mediterranean cuisine (Kava and it’s sister restaurant, Ilona as well as the fast casual, Anoush’ella are superb). Several excellent Spanish restaurants are home to the South End but Toro is my favorite. For sushi, I prefer the unpretentious Seiyo near Mass Ave. or Red Lantern. There are many options for pizza, but my favorites are Union Park Pizza (take out only) and PICCO (which stands for Pizza & Ice Cream Co.). In recent years, several Mexican and Latin restaurants have opened but my favorites are the relatively new Burro Bar and the longstanding Orinoco. I still blush thinking about my first time at Orinoco. In my haste to get inside, I accidentally knocked over Keith Lockhart. We fell into each other’s arms as we crashed into the wall so I suppose I can say I’ve hugged the famous conductor of the Boston Pops.
The list of great places to eat in the South End is long, and I’ve barely scratched the surface. If you’re looking for a suggestion, ask me, and I’ll be happy to make recommendations based on your preferences.
Favorite Bars in the South End: There are many places to enjoy a cocktail or drink, but if you want to enjoy live music go to the tiny and quite famous, Wally’s. It is one of the oldest jazz bars in America (opened in 1947) and has hosted some of America’s greatest jazz musicians. A few blocks over from Wally’s is Darryl’s Corner Bar & Kitchen, and in the opposite direction, up Tremont Street is the Beehive. All three locations have excellent live music and are places worth visiting. Darryl’s and the Beehive also have kitchens that crank out consistently good food if you’re hungry.
If you’re a beer drinker, go to JJ Foley’s, an Irish pub that has been operating in the South End since 1909. This place has a lot of character and serves a mean shepard’s pie. On the other end of the neighborhood, is a relative newcomer by comparison, Five Horses Tavern, which opened in 2013. Both places will make any beer drinker feel at home.
If you’re looking for something more kitsch, check out the subterranean, Polynesian bar and restaurant with great tiki drinks Shore Leave or longtime neighborhood favorite, Delux Cafe with its ticky-tacky decor and quirky staff. The bars you’ll mostly likely find Sergio and me at is the gorgeous 20+ seat bar at Boston Chops and the welcoming lounge at Burro Bar South End (if you like spicy drinks order the el Diablo). However, I also love the gorgeous U-shaped bar at Barcelona Wine Bar and the cozy wine bar at Aquitaine (they have an excellent Sancerre rosé by the glass).
Gay Bars in the South End: Only a few gay bars remain in the South End. Cathedral Station is located on Washington Street and is the only downtown gay bar with a patio. They cater to the gay sports leagues and the bear community. You’ll usually find an older crowd here, but all are welcome at this friendly bar. The other gay bar in the South End is Club Cafe. Over the years it has become increasingly mixed but they still market themselves as a gay bar. Club Cafe has the Napoleon Lounge where cabaret music is performed, a dance floor in the back and a dining room and bar at the front of the house. If you’re gay and in Boston, you’ll eventually end up at Club Cafe.
While it’s true that Boston has very few gay bars, Boston’s LGBTQ+ community is redefining what is a gay bar and claiming space to meet, have a drink, gossip, watch a game, etc… whether the establishment is marketed as a “gay bar” or not. Good examples would be Boston Chops South End, Burro Bar South End, Trophy Room, Anchovies, and Elephant Walk. On any given night you will see gay friends meeting for drinks and as a result the local LGBTQ+ community has come to think of these places as ‘unofficial’ gay bars. While they are no longer around, virtually every gay man in Boston thought of Pho Republique, Rocca, Tremont 647, Sister Sorel, and Stella as some of Boston’s best gay bars, yet none were marketed as such.
If you happen to be new to Boston or planning a visit, feel free to reach out with questions. If you’re familiar with Boston’s South End, your recommendations are welcome in the comments section.