See more of Boston's South End in the slideshow above.

This article was originally published on May 29, 2008; it has been recently updated to include new locations and current information.

One of Boston’s most beautiful neighborhoods and arguably one of its most culturally diverse, the South End has a rich history. Bordered by 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 U.S. 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 By the 1880s many of its wealthy founding families had been replaced by waves of immigrants from Ireland, Lebanon, and Greece, and tenements and settlement houses were built to accommodate them.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 same-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, 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 Bistro 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

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 and joggers, is dotted with community gardens maintained by local residents.

Wally’s Café

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. But don’t miss it before it closes: it’s open from 6:30 a.m. to 5 p.m. every day except Sunday.

Delux Café

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 is always loud. The TV is tuned to the Cartoon Network, and 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 are priced right, but Delux takes cash only.

Club Café

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 also has dancing and trivia nights as well as numerous special entertainment offerings. Late-night noshers can order lobster rolls, nacho fries, and individual pizzas from a bistro menu from 11 p.m. to 1 a.m. Friday and Saturday nights.

Anchovies

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.

Sibling Rivalry

525 Tremont St.
Among the South End’s trendy eateries, Sibling Rivalry, which features dueling menus from brother chefs David and Bob Kinkead, boasts the best personality. David and Bob each offer culinary riffs on seasonal ingredients. Take beef: David’s beef tenderloin steak diane with pepper crust, mustard-tarragon sauce, anna potatoes, onion crisps, and haricots vert versus Bob’s braised beef brisket with potato-onion pierogis, red cabbage, roasted salsify, and horseradish cream.

Hamersley’s Bistro

553 Tremont St.
With appetizers like crispy duck confit and entrées including spicy halibut and clam roast with bacon-braised greens, white beans, and black trumpet mushrooms, this bistro, owned by chef and BU alum Gordon Hamersley (CGS’71, SED’74), is a special occasion dining experience. It’s among the neighborhood’s more expensive restaurants, but it offers superb service, one of the city’s most imaginative menus, and during warm weather months, a classic alfresco dining experience. Watch Hamersley describe how he puts together a menu here.

The Red Fez

1222 Washington St.
Offering a full bar and a menu of Middle Eastern and Mediterranean food, including mezze (Middle Eastern tapas), served until 2 a.m., the Red Fez is a popular destination for large groups looking for a celebratory night out. Be sure to try a drink from the restaurant’s extensive cocktail menu, like the Forbidden Harem, a mix of sweet tea vodka, lemon-lime soda, and sour mix. And don’t miss the live Arabic music on Saturday nights.

Stella

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. Stop by between 4 and 6 p.m. Monday through Friday for inexpensive starters like marinated beets with goat cheese or spicy mussels in saffron cream.

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 hummus, cucumber, red onion, and sprouts sandwich or grilled portobello 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 advises Flour’s busy crowd to “make life sweeter…eat dessert first.”

Code 10

1638 Washington St.
Named for the police code for lunch break, this corner café is across the street from Flour. Its lunches tend toward the classics (ham and cheese, beef gyro) and draw fewer raves than those of its neighbor. But Code 10 offers a calmer atmosphere. And it has its own temptation for those with a sweet tooth: a selection of homemade ice cream that includes rum raisin, cookie dough, totally turtle, and purple cow.

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.

Syrian Grocery and Importing Company

270 Shawmut Ave.
Hookahs might be the biggest draw for college students, but there’s much more in this quirky grocery/cookware/specialty food store, built to serve the South End’s once sizable Syrian, Lebanese, and Greek community. Today, you can still find hazelnut praline, green pepper jelly, fig spread, and chutneys of all sorts. It also stocks kitchen necessities such as stovetop espresso makers and large serving platters. In the back are containers of olives and hard-to-find spices such as za’atar and wasabi-flavored sesame seeds.

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.”

SoWa Open Market

460 Harrison Ave.
Every Sunday (except for holiday weekends) from early May through late October, a parking lot in the SoWa district is transformed into an artisan market. Artists, farmers, florists, and craftspeople set up shop under white tents, with the vendors changing week to week. Selling time each Sunday is from 10 a.m. to 4 p.m.

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 Treatza Pizza and peanut butter oatmeal crunch. There’s also a huge selection of meat jerky (including duck, elk, and chicken), squeeze toys, and dinosaur-size bones for gnawing. The bully sticks—edible chew toys made out of animal tendon—are a popular option. It’s worth a look, even if you don’t carry your dog around in your handbag.

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 changing demographics, from Protestant to Irish Catholic. Designed in the Gothic revival style, it is 360 feet long and 120 feet high and boasts one of the country’s finest pipe organs. Today, the cathedral serves a diverse faith-based community, including English and Spanish 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.

Boston Center for the Arts

539 Tremont St.
Call the BCA the heart of Boston arts and theater. The complex supports five resident theater companies and houses an art gallery and studio space for local artists. One of the most interesting buildings in the BCA complex is the Cyclorama, a massive brick rotunda topped by a copper skylight dome, built in 1865, which is now included on the National Register of Historic Places. It has also served as a skating rink and a flower market. Today, this 23,000-square-foot space is a venue for artistic shows, public events, and private functions. In 2004, through a partnership with the Boston University–affiliated Huntington Theatre Company, the BCA opened the Stanford Calderwood Pavilion, Boston’s newest theater space, housing two separate venues: the 360-seat Virginia Wimberly Theatre and the 200-seat Nancy and Edward Roberts Studio Theatre. The Pavilion provides a second stage for the Huntington, as well as theater space for smaller companies.

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.

Learn about other neighborhoods around Boston here. Check out our list of South End tips on Foursquare.