One of Boston’s most beautiful neighborhoods, and arguably one of its most culturally diverse, the South End has a rich history. Bordered by the Back Bay, Chinatown, and Roxbury, the area’s primary commercial thoroughfare runs along Tremont Street, Columbus Avenue, and Harrison Avenue. Most of the residential cross streets are named after the towns (Dedham, Newton, Canton, Dover, etc.) that were served by the former Boston and Providence Railroad, which originally bordered the South End.
Developed in the mid-19th century to relieve overcrowding in downtown Boston and Beacon Hill, the neighborhood was originally a narrow strip of land, surrounded by salt marshes, connecting Boston to Roxbury. The South End was created with landfill from nearby Needham. Charles Bulfinch, one of the nation’s most prominent architects (the Massachusetts State House, the Boston Common, and much of the US Capitol), was hired to design the new neighborhood.
Today, Bulfinch’s imprint can still be found in the area. Tree-lined streets are graced by connected brick bow-front townhouses surrounded by iron gates and built around a series of shaded pocket parks, many with elegant fountains. In 1973, the South End was listed on the National Register of Historic Places as “the largest urban Victorian neighborhood in the country.”
The neighborhood has long had cycles of boom and bust. By the 1880s many of its wealthy founding families had been replaced by waves of immigrants from Ireland, Lebanon, and Greece, and tenements and settlement houses were built to accommodate them. During the 1940s, the South End became home to a vibrant African American middle class. At the same time, it began to attract gay men and women drawn by the many single-sex rooming houses that provided them with social cover.
By the early 1960s the area had become synonymous with crime and poverty. But the neighborhood underwent another gentrification beginning in the late 1970s, led primarily by gay men.
Today, the South End is one of the city’s most diverse neighborhoods, both economically and racially. Still home to a large gay community, the area also has a sizable Hispanic population. Seven-figure townhouses abut several large subsidized housing projects. And the area has become a popular place to work for artists.
Pricey restaurants like chef Barbara Lynch’s Butcher Shop, B&G Oysters, and Aquitaine Bar à Vin Bistrot draw locals as well as people from surrounding suburbs. But there are still plenty of places to grab good, cheap food and lots of trendy boutiques and performing arts venues. Below is a sampling.
Southwest Corridor Park follows the Orange Line nearly five miles, from Forest Hills in Jamaica Plain to Back Bay station. A stroll along the section between the Mass Ave and Back Bay subway stops is a great way to start a visit to the South End. The gently meandering path, popular with dog walkers, joggers, and cyclists, is dotted with community gardens maintained by local residents.
427 Massachusetts Ave.
The sole remainder of a nexus of famous jazz clubs (among them the High Hat, the Savoy Ballroom, and the Wig Wam), Wally’s has been a neighborhood institution since 1947. The club took its name from owner Joseph Walcott (better known as Wally). As jazz’s popularity waned, in the early 1960s Walcott began featuring up-and-coming artists from Boston’s nearby conservatories. Today, the club continues to provide a platform for emerging jazz talents. Wally’s Café offers live music 365 days a year.
Berkeley Perk Café
69 Berkeley St.
With booths, high-top tables, and comfy wingback chairs, Berkeley Perk is a friendly spot to stop in for a scone or sandwich. It also serves a cup of coffee you’ll never forget. The place is cozy, but high ceilings, yellow walls, and a huge storefront window give it the illusion of being bigger than it is.
100 Chandler St.
You can hear Delux before you see it. The music in this crowded, windowless hipster dive bar/restaurant tucked away from the more posh South End eateries varies, but it is always loud. The walls are plastered with old LP covers and festooned with Christmas lights. The drinks (including bottles of Schlitz and Narragansett tall boys) and better-than-dive-bar menu (quesadillas, skirt steak tacos, scallops, and cubano sandwiches to name a few) are priced right, but bring cash. Delux does not take credit cards.
209 Columbus Ave.
When Club Café opened in 1983, its owners say, it was the first gay club in Boston to have windows—patrons didn’t have to hide from passersby. Today, the place is still a popular gay restaurant and bar; it serves lunch and dinner, as well as a popular Sunday brunch. The club also has dancing and trivia nights as well as numerous special entertainment offerings. Entrees, including pork chops, seafood risotto, meatloaf, and grilled salmon are served till 11 p.m., but diners can order from the bar menu until midnight on weekdays and until 1 a.m. on Fridays and Saturdays.
433 Columbus Ave.
In a neighborhood where shops claim a “cheese philosophy” and restaurants promise “the art of Thai cuisine,” it’s nice to know that a place like Anchovies still exists. This is authentic Italian. Take a seat at one of the high booths in the dark restaurant, and you’ll be fed and treated well at a reasonable price.
517 Columbus Avenue
Named for the mother of its executive pastry chef, Café Madeleine serves up elegant, authentic French pastries. The café has an open show kitchen where customers can watch as chefs turn out macarons, tartes aux pommes, éclairs, and delicious fruit- and chocolate-filled croissants. They also serve a lunch menu featuring classic savory French dishes like croque monsieur and quiche lorraine.
505 Tremont St.
Featuring one-of-a-kind women’s clothing, handcrafted jewelry, trendy shoes, and irresistible accessories from around the globe, Sooki embodies the eclectic, creative spirit that characterizes the South End. The boutique carries work by designers from Italy (e.g., She’s So), France, China, Japan, and Belgium, in addition to American designers like 360 Degrees, Isda, and New York 77. The boutique is closed Mondays.
511 Tremont St.
One visit to this trendy men’s boutique and you’ll want to claim all of its stylish clothing for your personal uniform. Carrying the hippest selections of sweaters, chinos, wallets, and more from brands like Scotch & Soda, Ben Sherman, and Fred Perry, Uniform makes it easy to create the look—from classic to modern—that suits you best. Deciding on what items to buy? That’s the hard part. Not to worry. The helpful staff is more than happy to assist you on your hunt for what’s hip. Note: the boutique is closed Mondays.
513 Tremont Street
Known for its thin-crust pizzas and homemade ice cream, Picco is a South End favorite. The casual neighborhood restaurant offers soups, salads, pastas, sandwiches, and pizzas (which, the menu warns, are cooked “well done with some char”). Picco’s worldly wine menu, featuring wines from Italy, France, Austria, California, and Spain, and its extensive beer offerings (from pale ales to ciders, lagers, and stouts) are yet another reason to visit this Italian restaurant.
Barcelona Restaurant and Wine Bar
525 Tremont Street
This Spanish tapas restaurant has a friendly staff, an impressive wine cellar, and the delicious flavors of Spain and Portugal. The South End location features a warm walnut décor, a popular brunch, and special dining events throughout the year. The dinner menu offers tapas, salads, and larger plates for two or more people. Late-night eaters are also in luck: the kitchen is open until 1 a.m., seven days a week.
Boston Center for the Arts
539 Tremont St.
Among Boston’s most vibrant cultural hubs, the Boston Center for the Arts (BCA) supports three resident theater companies and houses an art gallery and studio space for local artists. One of the buildings in the complex is the Cyclorama, a massive brick rotunda built in 1884 and topped by a copper skylight dome, which is included on the National Register of Historic Places. A former skating rink and a flower market, the 23,000-square-foot space is now a venue for artistic shows, public events, and private functions. In 2004, through a partnership with the Huntington Theatre Company, the BCA opened the Stanford Calderwood Pavilion, Boston’s newest theater, housing two separate spaces: the 370-seat Virginia Wimberly Theatre and the 200-seat Nancy and Edward Roberts Studio Theatre. The Calderwood serves as a second stage for the Huntington, as well as a venue for a number of smaller companies.
541 Tremont St.
This exuberant bohemian restaurant–music venue features hip vibes, cool tunes, and delicious plates. Nosh on tasty appetizers like “fall-off-the-bone” baby back ribs, and then go for one of the entrees. We recommend the Beehive prime burger. With live music every night, this is a great place to hear local musicians and up-and-coming jazz bands, like Bagels the Dog. One visit and you’ll see why the Beehive has become one of the city’s premier nightlife destinations.
Banyan Bar & Refuge
553 Tremont Street
Located between the Boston Ballet and Boston Center for the Arts, Banyan Bar & Refuge offers a modern twist on Asian cuisine. Open only for dinner, the restaurant has a gray and chartreuse color scheme and large twig chandeliers. The menu offers such delicacies as fried pig tails with gremolata and garlic black bean sauce and calamari escabeche with Asian pear, whipped tofu, and burnt cabbage. The restaurant’s patio is an ideal place to enjoy a meal during warm weather months. It also offers a selection of sake, white and red wines, beer, and specialty cocktails.
560 Tremont St.
History often repeats itself, and at Kitchen, it does so intentionally. Chef Scott Herritt has created an eclectic menu inspired by recipes from a variety of classic sources, including Irma Rombauer’s influential Joy of Cooking, first published in 1931; Hannah Glasse’s 1774 The Art of Cookery Made Plain and Easy; and Julia Child’s Mastering the Art of French Cooking, published in 1961. The menu gives the date of each dish’s conception, transporting diners back in time. For example, the scrumptious sole, pan roasted and served with parsley, lemon, buttery potatoes, zucchini, and yellow squash, is dedicated to Child and appears on the menu with the date November 2, 1948, beneath it. Other popular menu items include lobster thermidor; a beef tenderloin served with foie gras, crisp toasted brioche, black truffle, and madeira; and a coffee- and cocoa-crusted venison, served with sweet potatoes, apple, and Brussels sprouts. Kitchen also serves a delicious brunch on weekends. Whether you’re a culinary history buff or not, the food at Kitchen is sure to please.
584 Tremont St.
This Mediterranean bistro is noted for its mix of French and Italian comfort food. Some of the most popular dinner items include a delicious roast chicken, rigatoni served with fennel sausage, and a mouthwatering veal scaloppini. Metropolis is equally famous for its weekend brunches. Be sure to try the huevos rancheros, the banana pancakes, and the black bean hash. Expect to wait in line if you’re there for brunch. Dinner reservations are strongly encouraged.
South End Athletic Company
652 Tremont St.
Founded by former BC track stars Dan Fitzgerald and Justin Burdon, South End Athletic Company (SEAC) was created with the goal of putting a fun and fashionable spin on traditional running gear and fusing fashion with function. The store is decorated minimally, but don’t let that fool you—SEAC carries the running industry’s top brands, like Nike, Asics, and Brooks, and has an impressive, rainbow-colored wall of shoes sure to attract both runners and nonrunners. The store also offers several free run clubs for runners of all levels, as well as professional personal coaching. One visit and you’ll understand why SEAC was recently named best running store by Boston magazine.
1395 Washington St.
If you haven’t already, you’ll want to make the Gallows your new neighborhood hangout. Sure, Beacon Hill has the original Cheers, but the welcoming staff at this local gem will make you feel like everyone knows your name, too. Popular for its cocktails (we recommend the Angelina, gin, grapefruit, yellow chartreuse, and orange bitters), the Gallows has a delicious seasonal menu that changes weekly, depending on what’s fresh.
Cathedral of the Holy Cross
1400 Washington St.
The mother church of the Roman Catholic Archdiocese of Boston, the cathedral opened in 1875, signaling the city’s demographics shift from Protestant to Irish Catholic. Designed in the Gothic revival style, it is 364 feet long and 120 feet high and contains one of the country’s finest pipe organs. Today, the cathedral serves a diverse faith-based community, including English- and Spanish-speaking congregations, a German apostolate, and Ge’ez Rite Catholics from Egypt, Eritrea, and Ethiopia, as well as a large traditional Latin Mass community. It is the largest Catholic church in New England and has played a critical role in the life of Boston’s evolving immigrant communities.
Boomerangs Special Edition
1407 Washington St.
Boomerangs Special Edition is the high-end version of resale stores of the same name, all of whose proceeds benefit the AIDS Action Committee, a nonprofit that provides services and advocacy in the fight against HIV/AIDS. Like the other Boomerangs, this one sells used clothing, furniture, housewares, and jewelry, but the goods are higher end. If you’re looking for elegance, but don’t want to pay elegant prices, this is the place to shop for designer fashion at a very good price. Best of all, you’ll be supporting a worthy cause.
Foodie’s Urban Market
1421 Washington St.
Sure, you can pick up a gallon of milk and some eggs here. But this is the South End, and it’s not just the hardwood floors and stamped tin ceiling that make this place different from your average neighborhood market. The produce bins include hard-to-find items such as fiddleheads and fresh apricots. The deli offers prepared lunch dishes like carrot raisin salad, artichoke chickpea feta salad, and macaroni and cheese. There’s also a salad bar, with Greek, Caesar, and fruit salads for a quick snack, befitting the store’s slogan: “For gourmet and everyday.”
1525 Washington St.
This dining destination offers modern twists on authentic Italian dishes, like pork Milanese and seafood risotto. With its outside dining patio, Stella is a great place for a summer meal. Although the entrees can be pricey, the restaurant offers discounted appetizers between 4 and 6 p.m. Monday through Friday, including a delicious starter featuring marinated beets with goat cheese. The restaurant also serves a late night menu on Fridays and Saturdays from 11 p.m. to 1 a.m.
Flour Bakery and Café
1595 Washington St.
Blue hospital scrubs and stethoscopes are a common sight among the outdoor lunch crowd at this renowned bakery and sandwich shop a couple of blocks from the BU Medical Campus. Indoors, patrons stake out a square foot or two while waiting for a roast beef sandwich with horseradish mayo, crispy onions, and tomato or grilled Portobello mushroom melt with roasted tomatoes and basil pesto. The pastries—among them the “ooey-gooey caramel nut” tart and the lemon-raspberry cake—are legendary. A saying chalked on the menu board urges Flour patrons to “make life sweeter…eat dessert first.”
1638 Washington St.
Taking its name from police speak for lunch break, this corner café, located directly across the street from Flour, offers a full menu all day long, including breakfast sandwiches, panini, salads, and soups. Its lunches tend toward stalwart sandwich classics like smoked ham and cheese, turkey club, and beef gyro. And while it can’t compete with Flour’s myriad sweets, it does offer its own temptation for those with a sweet tooth: a selection of Richardson’s ice cream that includes such favorites as maple walnut, cookie dough, totally turtle, and purple cow.
1704 Washington Street
This Barcelona-style tapas bar serves traditional and modern small plates made with local and sustainable ingredients, as well as an eclectic wine list and cocktail menu. Toro is open for lunch Monday through Friday and dinner seven nights a week. They also serve a popular Sunday brunch. Dinner reservations are not accepted, so plan to arrive early to get a table. Some favorites include Croquettas de Bacalao (salt-cod fritters with tempura lemon rings and aioli), Gambas al Ajillo (griddled garlic shrimp with cascabel chilies, parsley, and lemon), and Empanada de Cabra (spicy curry goat and potato empanada with cucumber, yogurt, and cilantro.
59 East Springfield St.
This tiny, unpretentious sandwich shop’s name says it all. Breakfast and lunch are the only options here, but when homemade soups, pressed sandwiches, and bagelwiches taste this good, who needs dinner? Just across the street from Boston Medical Center, Blunch is a popular destination for med students, faculty, and staff (you can even call in your order ahead of time). Try the Giving Tree, a scrumptious combination of smoked turkey, cheddar cheese, thinly sliced green apples, honey Dijon dressing, and baby greens on multigrain bread, and top it off with one of the eatery’s oh-so-gooey triple chocolate chip cookies.
SoWa Open Market
460 Harrison Ave.
From May through late October, a parking lot in the SoWa district is transformed into an artisan market every Sunday (save for holiday weekends). Artists and an array of craftspeople set up shop under white tents, with vendors sometimes changing from week to week. There’s also a farmers market at 500 Harrison Ave. The market features numerous food trucks, at 540 Harrison Ave., so you can fuel up while shopping. Selling time each Sunday is from 10 a.m. to 4 p.m.
Cinquecento Roman Trattoria
500 Harrison Avenue
Cinquecento (500 in Italian) offers a contemporary, casual, and energetic Roman trattoria–like atmosphere. As guests enter the restaurant, they walk up an illuminated cast-iron and glass staircase to the main dining room and bar, with its reclaimed beams and bricks and Italian leather banquettes and booth tables. In true trattoria fashion, the dining room also has two communal tables. The downstairs private dining room is perfect for small parties. The 60-seat patio is open during the warmer months and is a big draw with locals. Cinquecento offers a dinner menu and a weekends-only brunch menu. Dinner menu standouts: bruschetta con finocchiona, grilled bread with warm ricotta, finocchiona, and pickled delicate squash, linguini alla vongola, with tender clams, vino bianco, toasted garlic, and chili, and prosciutto-wrapped veal tenderloin with cabbage fonduta and marsala. Cinquecento also offers complimentary parking in an adjacent lot.
Gaslight Brasserie du Coin
560 Harrison Ave.
With its handcrafted zinc bar, beamed wooden ceilings, mosaic tiles, and vintage mirrors, this classic Parisian brasserie puts a modern twist on classic French style. Lively and often loud, Gaslight offers a variety of seating options—from café and communal tables to booths and banquettes—as well as a lovely wine selection (all French) and some of the best steak frites you’ll find anywhere in Boston. A bit on the expensive side, Gaslight is still a solid choice for any time of day, even weekend brunch. An outdoor patio provides a romantic setting for a candlelight dinner during warm weather.
Estragon Tapas Bar
700 Harrison Ave.
Estragon offers superb tapas at reasonable prices. Billing itself as “the only Spanish restaurant in Boston with a native Spaniard at its helm,” the restaurant offers such classic dishes as duck confit served with a fig-balsamic jam and Marcona almonds; roasted Brussels sprouts served with chorizo and golden raisins (one of the restaurant’s most popular items); and paella. It’s a good place to enjoy a quiet weeknight meal. On weekends, the place is bustling and reservations are recommended. An outdoor patio offers patrons great people-watching during warm-weather months.
Bobby from Boston
19 Thayer St.
Bobby’s is the place to go for men looking for distinctive clothing and accessories from another era. The vintage clothing store offers a large assortment of men’s hats, suits, shoes, vests, and coats, as well as flasks, pipes, and yes, even monocles. Spread out over three floors, this boutique is a must for men who want to add some classic pizzazz to their wardrobe. The store also has a small selection of women’s vintage clothing and accessories.
Polka Dog Bakery
256 Shawmut Ave.
This palace of pooch pampering was inspired by a one-eyed dog named Pearl, who would perform a little polka in an effort to see people with her good eye. In addition to walls of fashion-forward collars, leashes, and dog sweaters, display cases are crammed with doggie treats such as peanut butter Wonder Nuggets and Chicken Little Sfizis. There’s also a huge selection of meat jerky (including duck, cod, and chicken), squeeze toys, and dinosaur-size bones for gnawing. The bully sticks—edible chew toys made out of animal tendon—are popular. It’s worth stopping by, even if you don’t carry your dog around in your handbag.
South End Formaggio
268 Shawmut Ave.
To get to the artisan cheeses that have made Formaggio famous, you need to first make your way through the handmade sweets, pastas, pâtés, spices, olive oils, and specialty items ranging from fig relish to organic Tuscan fruit preserves. This wonderful food specialty shop offers the best cheese selection in Boston, as well as artisan beers and carefully chosen wines that include some inexpensive everyday table wines. The staff is knowledgeable about everything they sell. This store is a must for foodies.
274 Shawmut Ave.
Established in 2009 by mother-daughter retailers Lisa Kupsc and Dani McDonald, this women’s boutique sells modern bohemian chic apparel that’s easy to wear. In addition to skirts, tops, pants, outerwear, and intimate apparel, Flock has unique jewelry, bags, scarves, and gloves, as well as gifts for the home. The staff is friendly and knowledgeable. One visit and you’ll be hooked.
The Franklin Café
278 Shawmut Avenue
This charming café has a innovative approach to traditional American cuisine, with dishes like turkey meatloaf with fig gravy and chive mashed potatoes; shrimp and grits with chorizo, charred lime, and a rum glaze; and rubbed pork tenderloin with a sweet potato–stuffed chile relleno. Although the kitchen is open only for dinner, the full menu is available every night until 1:30 a.m. The bar offers local microbrews on tap, a diverse wine list, and an innovative cocktail menu. Try the La Luna Roja with Thai chili–infused reposado, aperol, hibiscus, lemon, and smoked sea salt. Boston magazine awarded the café a Best of Boston award in 2014.
South End Buttery
314 Shawmut Ave.
Owner Richard Gordon (LAW’89) has created a welcoming bakery and café that will satisfy you and your canine companion (dogs are welcome on the patio). The restaurant is committed to using organic, all-natural, locally raised and grown ingredients whenever possible. The lunch menu includes crowd pleasers like the always classic grilled cheese and tomato (gruyere, aged cheddar, and tomato on sourdough) and curried chicken salad (romaine, roasted chicken breast, green apples, grapes, celery, cashews, Major Grey’s chutney, and curried mayo). The dinner menu features comfort food like meatloaf (served with baked sweet potato wedges, grilled asparagus, and pearl onion gravy), and eggplant parmigiana (with house-made marinara, fresh mozzarella, and garlic-steamed organic greens). Chances are you won’t be able to ignore the sweet temptations from the bakery. You can’t go wrong with a chocolate-dipped macaroon or a raspberry crème cupcake. And for your four-legged friend? The Buttery offers fresh biscuits from neighbor Polka Dog Bakery.
472 Shawmut Ave.
Named a Best of Boston by Boston magazine in 2013, El Centro is one of the standouts among the city’s recent surge in south-of-the-border dining. Step inside this hip spot and be surrounded by vibrant Mexican street art, including a hand-painted mural along the back wall, as well as portraits of Mexican artist Frida Kahlo and film idol and singer Pedro Infante. The menu is equally vibrant, featuring entrees like camarones papanila (shrimp wrapped in bacon and stuffed with cheese, served with rice and avocado). Chef and owner Allan Rodriquez, a native of Sonora, whips up family recipes every night. El Centro also offers a small, but choice selection of wines, beers, and sangrias.
477 Shawmut Ave.
With its colorful curtains, warmly painted walls, and friendly staff, this casual Venezuelan restaurant gives the feel of dining in someone’s home. Orinoco’s menu includes old family recipes that blend dishes indigenous to the Andes and the Caribbean. Servings are generous and reasonably priced. Inspired by taguaritas—the small, rustic roadside eateries found everywhere in Venezuela—the restaurant offers mouthwatering options like empanadas with shredded beef and the pepito de carne, French bread stuffed with sautéed onions, grilled flank steak, red peppers, tomatoes, and a sweet special sauce. Don’t leave without trying the torta fluida, a molten chocolate cake made with 100 percent Venezuelan dark chocolate.
Getting there: The BU Shuttle (BUS) runs from the Charles River Campus to the Medical Campus, which borders the South End. Nearby MBTA stops include Massachusetts Avenue and Back Bay on the Orange Line and Symphony, Prudential, and Copley on the Green Line. The Silver Line bus also runs up and down Washington Street.
Click on the points in the map above for more information on the places listed in our guide to the South End area.