Weekend in Boston’s South End

The South End is the hub of Boston’s gay scene

About 25 years ago, if you’d predicted that Boston’s South End would today have one of the hottest real-estate markets in the Northeast, most people would have laughed in your face. But just as it happened in decaying city neighborhoods throughout the United States, a few gutsy urban pioneers – many of them lesbians and gay men – began moving into this historic but run-down neighborhood, and over time it blossomed. The South End is now the hub of Boston’s gay scene, and it’s a terrific part of the city to spend a weekend of wining, dining, and bar-hopping.

Although the South End languished for many decades, the neighborhood was planned and developed with great fanfare. Most of the neighborhood’s handsome bow-front redbrick homes, many of them embellished with elaborate molding and wrought-iron grill work, were built in the 1850s and purchased by upper-class merchants and professionals. By the turn of the 20th century, however, the newly created Back Bay and other Boston neighborhoods had become more desirable, and a swath of rail lines had cut the South End from the rest of the city. The bloom was off the rose.

Over the next 60 years, middle-class blacks and immigrant Middle Easterners, Asians, and Latin Americans moved in. For a time the South End remained economically stable and unusually diverse, by urban New England standards, in terms of race and ethnicity. But professionals began moving elsewhere following World War II and the general economic malaise that plagued Boston, and by the 1960s the South End was a dicey area.

A mix of artists, hippies, adventuresome professionals, and lesbians and gays soon began to recognize the neighborhood’s tremendous potential – particularly those tall, dignified bow-front houses. The transition from blighted neighborhood to gay ghetto to the more eclectic South End of today has been gradual and at times uneasy. There remains some economic, racial, and cultural diversity, but each year – as market forces drive up housing costs – the neighborhood becomes increasingly wealthy and homogenous.

It’s impossible not to notice the South End’s considerable charms, however, especially as you stroll along the narrow tree-shaded streets with brick sidewalks and old-fashioned-style street lamps. And the neighborhood does have a remarkably integrated gay and mainstream personality. The South End’s main commercial spines, Columbus Avenue and Tremont Street, are loaded with gay-popular restaurants and businesses. Meanwhile, many budget-restricted queers have migrated in a southerly direction, helping to rejuvenate the once undesirable blocks along Shawmut Avenue and Washington Street.

There aren’t many lodging options in the South End, but the two here are extremely popular with queer guests. The upscale and romantic Clarendon Square B&B has just three rooms, but innkeepers Stephen Gross and Michael Selbst operate this exceptional property with the level of service you’d expect at a luxury hotel. Rooms are open and airy, with eclectic and stylish furnishings, working fireplaces (in all but one), CD players, and phones with voice mail. The bathrooms are a real treat, with either a two-person shower or whirlpool tub, plus limestone floors and French fixtures. The six-story 1860s building has a spectacular rooftop sundeck and a Victorian parlor with a grand piano.

If you’re looking to save a few bucks, consider the 56-room Chandler Inn. With a gay bar (Fritz) on the ground floor, this otherwise ordinary hostelry is one of the most gay-frequented in the Northeast. The small but clean guest rooms, which have been extensively refurbished in recent years, have blond-wood furnishings and small writing desks; the bathrooms are very small. You’ll be treated like family by “family,” and the price is fair.

The South End is just a short walk, however, from the many chain hotels around Copley Square, and also from the Theater District, which has several gay bars. In the latter neighborhood, you might consider the 1925 Wyndham Boston Beacon Hill hotel, a reasonably priced 304-room property whose compact guest rooms have been jazzed up with reproductions of 18th-century antiques and stately prints from the Museum of Fine Arts. There’s also the Oasis Guesthouse, an excellent, reasonably priced gay-male-oriented inn that’s just a 15-minute walk from the South End. This lively, social guest house comprises two adjoining brick buildings; rooms are small but bright with oak furnishings and a mix of antiques and contemporary pieces. The staff is outgoing and helpful, and there’s a deck for sunning.

You may have to leave the South End to take in Boston’s dozens of great museums, or to catch a show or a concert, but you could spend a month in this compact neighborhood and enjoy a memorable dinner at a different restaurant every night. This is one of the East Coast’s great dining neighborhoods, and it’s difficult to narrow down the many fine choices to just a few. One of the first restaurants to attract serious diners to the South End, Hamersley’s Bistro has both a cafe and a more formal dining room in an elegant but spare space inside the Boston Center for the Arts. Around the corner at Aquitaine, duck-and-foie gras ravioli and coq au vin with tarragon and white wine are among the stars. This beautiful-peopled yet surprisingly low-key bistro is usually packed.

Attached to the gay bar complex of the same name, Club Cafe is popular with men and women seeking a comfy spot for a romantic date. The New American fare isn’t bad, although the service sometimes lags. There’s also an affordable cafe menu with sandwiches and munchies. A great choice for creative Southwestern fare is Masa, where concoctions like lobster tail, sweet corn, and goat cheese tamales earn high praise. Inexpensive Baja Cantina serves hearty Tex-Mex fare like Anaheim chiles rellenos and a piquant starter of savory plantains with chipotle avocado salsa. The setting is loud and festive, and you’ll find plenty of “friends of Dorothy” among the staff. You’ll be hard-pressed to find better food and cozier environs in the South End than at the Franklin Cafe, where the seasonal contemporary menu might offer roasted-turkey meat loaf with spiced fig gravy. The restaurant’s bar draws a stylish gay/straight crowd into the wee hours. A handsome and highly gay-popular java joint in the heart of the neighborhood, Francesca’s scores high marks for its welcoming employees, comfy window-front counter seating, and delicious desserts.

Technically, there are just three queer bars in the South End. The aforementioned Club Cafe is the domain of preppy professionals – there’s a sophisticated cocktail lounge-cabaret that’s popular with suits after work (this section is the most mixed male/female), and a larger, cruisier, and more attitudy video bar in back. Formerly a fixture of the city’s leather scene, the Eagle has gradually shifted into a more laid-back but fiercely popular cruise- and-chat bar with a mostly male, thirtysomething crowd. This intimate, if cramped, tavern with a popular pool table is like any other pick-up spot but for being unusually friendly – the cheap and potent drinks are also a plus. Finally, the dapper-looking Fritz is often described as Boston’s gay Cheers – it’s busiest around happy hour and on Sunday afternoons.

There are several additional nightlife options just a short walk from the South End, including the long running Luxor/Jox compound, with a downstairs sports bar and a trendier upstairs video lounge. Lesbians have rightfully complained for years about the city’s barely breathing women’s nightlife scene, but Circuit Girl sponsors a weekly Friday-night party in the nearby Theater District that’s always jamming. Held at the snazzy Club Europa, this kicky party rivals any such event in New England. On Saturdays, the same venue hosts a see-and-be-seen gay men’s party called Buzz. The bilevel space has a dance floor, a swanky lounge, and a third room with two pool tables. Across the street is another long-time gay- clubbing favorite, Vapor, which hosts a variety of lively theme nights (classic disco, Latino, etc.).

The South End’s fortunes have waxed and waned over the years. These days it’s enjoying a particularly long and fruitful boom period. Whether for a quick weekend getaway or a longer vacation, it’s a wonderful base for exploring Boston.