See more of Jamaica Plain in the slide show above. Photos by Robin Berghaus and Cydney Scott. Slideshow by Grace Ko.

This story was originally published on June 27, 2008; it has been recently updated to include new locations and current information.

There is lot to do in Jamaica Plain. Just 15 minutes from BU by bike, bus, or T, JP is one of Boston’ s most diverse and most happening neighborhoods.

You won’t find chain stores here. What you will find is a community committed to the environment, fair-trade commerce, and sustainable agriculture, a place that’s hip and definitely way left-of-center when it comes to politics.

Once described as the “Eden of America,” JP evolved after the Civil War from a series of large farms to one of the country’s first streetcar suburbs. The neighborhood is a key part of the city’s famed Emerald Necklace, a seven-mile series of contiguous parks designed by renowned landscape architect Frederick Law Olmsted in the late 19th century.

The Great Outdoors

Jamaica Pond
Jamaicaway and Pond Street

To get to Jamaica Pond, follow the bike path that runs along the Emerald Necklace from the Landmark Center to JP. Covering 68 acres, Jamaica Pond is a great place for a bike ride or stroll. This kettle pond formed by glaciers was once a reservoir for the city of Boston. Today, holders of a Massachusetts fishing license can fish the pond. Sailboats and rowboats are available for rent by the hour during the summer months.

Arnold Arboretum
Arborway

The crown jewel of all of JP’s parks, the Arnold Arboretum offers a stunning landscape that changes with the seasons. Like Jamaica Pond, the Arboretum is another link in the city’s Emerald Necklace. Originally owned by Harvard University, the Arboretum was established in 1872, making it the oldest public arboretum in North America. It was deeded to the city of Boston in 1882, and Harvard was given a 1,000-year lease and operates the property. Today, it is one of the world’s preeminent research institutions, with more than 15,000 plants spread across 265 acres. The Arboretum is famous for its annual Lilac Sunday, held each May to celebrate and showcase its world-class collection of lilac trees.

Forest Hills Cemetery
95 Forest Hills Ave.

One of the premier examples of the garden cemetery in America, Forest Hills was created in 1848 to replace old colonial graveyards in what was then the city of Roxbury. The cemetery, set on 275 acres, was designed not only as a place to mourn the dead, but to contemplate nature. Many famous Americans are buried there, among them the abolitionist William Lloyd Garrison, Nobel-winning playwright Eugene O’Neill, and poets Anne Sexton and e. e. cummings. The cemetery also includes wonderful examples of Victorian architecture and spectacular sculptures, including a towering bronze angel created by Daniel Chester French, famous for the Lincoln Memorial, in Washington, D.C.

The park-like setting is ideal for strolling and contemplation, with its woodlands, grassy slopes, waterfall, fountain, and man-made Lake Hibiscus. The crematory at Forest Hills was the first built in the United States. The cemetery was added to the National Register of Historic Places in 2004. Guided tours are available and summer concerts are offered in the chapel.

Hyde Square

El Oriental de Cuba
416 Centre St.

Hyde Square is home to a large Hispanic community, much of it anchored by the El Oriental de Cuba restaurant, a neighborhood fixture since 1994 and possibly the best Cuban restaurant in Boston. This no-frills place offers up appetizers like mofongo (mashed green plantains with pork rinds in garlic sauce); a variety of rice dishes, including rice with spicy octopus; and classic fare including ropa vieja, braised oxtail, and caballo steak topped with fried eggs. Menus are in both Spanish and English.

The Video Underground
385 Centre St.

Created to offer Boston cinephiles an extensive selection of independent films, Video Underground has more than 15,000 titles, including many that you won’t find online or at chains like Blockbuster. The knowledgeable staff researches films to add to the store’s collection on a daily basis. The store also offers local artists a chance to put their work on the shelves for rental. You can buy or rent VHS and DVD films here, and the salesclerks will happily order, at no extra cost, any available title they don’t have in stock. The Video Underground screens films in its backyard every Thursday night during the summer. Cost is $5.

Brendan Behan Pub
378 Centre St.

Popular with locals, “the Behan,” as it’s called, has been named one of the four best beer haunts in America by Interview magazine. This classic Irish bar is famous for its large selection of draft and bottled beers, including dark ales, stouts, and lagers. And as the pub’s devoted clientele will tell you, the Behan is also famous for conversation. You’ll find no TVs or pinball machines here, just knots of people engrossed in talking. And dogs. The Behan is one of the few establishments that actually welcomes canines.

A Taste of History

Loring-Greenough House
12 South St.

A superb example of Georgian Colonial architecture, the Loring-Greenough House is one of the oldest structures in JP. Built in 1760 by Joshua Loring, a Colonial American commodore in the English navy, the house saw a number of uses after English Loyalist Loring returned to England at the start of the American Revolution. The house was used as a military hospital during the Battle of Bunker Hill. In 1784, it was bought by the Greenough family, who occupied it until 1924, when it was saved from demolition by a group of civic-minded women. The house is open to the public each Sunday between noon and 2 p.m. from April through December. Visitors will see American furniture and decorative arts from the 18th through the early 20th centuries and archival material chronicling the history of Jamaica Plain. Special exhibits and concerts are also held at the house.

The Footlight Club
7A Eliot St.

Founded in 1877 with the mission of providing “pleasant and useful entertainment by the aid of drama,” this is the oldest community theater in the country. And yes, it still produces enjoyable dramas, musicals, and comedies, all cast with local nonprofessional actors.

The Eliot School
24 Eliot St.

In 1676, 38 residents of Jamaica Plain donated land to support a school. Funded by an endowment from local farmer John Eliot, the school educated Africans, Native Americans, and Colonial children before turning its focus to the arts in the late 19th century. Alarmed at how “manual arts” like woodworking, sewing, and bookbinding were disappearing in Boston, the Eliot School began offering courses in such crafts for schoolteachers, adults, and then for children in after-school programs.

Today the Eliot School of Fine & Applied Arts offers courses for children and adults in woodworking, sewing, fiber arts, drawing and painting, photography, and bookbinding. Classes offer a modern twist on many of these art forms: there are courses in drawing for comics and cartoons, digital photography, even how to market yourself as an artist.

Still operating out of its original 17th-century schoolhouse, the Eliot School has twice yearly sales of art created by faculty and students, in June and December.

Centre Street

Jamaica Plain’s main shopping and dining venues can be found along Centre Street, the main artery cutting through JP Center. Below are highlights.

Salmagundi
765 Centre St.

Salmagundi’s owners, husband and wife Jessen Fitzpatric and Andria Rapagnola, believe that there’s a perfect hat for every man and woman, and their shop has more than 7,000 to choose from. In addition to chapeaus of every stripe, the boutique offers a wonderful selection of handbags, jewelry, men’s ties, belts, and wallets—even flasks. The store also offers cleaning and blocking services.

Boomerangs
716 Centre St.

Love vintage clothing and want to support a good cause? Stop by this secondhand shop, which carries a wide selection of men’s, women’s, and children’s used clothing, as well as used furniture, electronics, toys, art, books, and CDs. All sales benefit the AIDS Action Committee of Massachusetts. The store’s inventory changes often as people donate goods constantly, so you’ll want to visit frequently. It has some real bargains, and if you’re looking to stock a new apartment, you cannot do better. And its window displays are works of pop art.

Wonder Spice Café
697 Centre St.

The small Wonder Spice Café bills itself as both a Cambodian and a Thai restaurant, offering such stalwarts as pad thai, chicken satay, and sweet chili shrimp alongside more exotic fare. Try the Phnom Penh Noodle Soup, a traditional Khmer soup with rice noodles, bean sprouts, and fried garlic, flavored with lime juice and scallions, and drunken noodle, large rice noodles stir fried with eggs and vegetables in a hot basil sauce. Wonder Spice is open for lunch and dinner.

Fire Opal
683 Centre St.

If you’re looking for an unusual wedding or birthday gift, a visit to Fire Opal is a must. The store has a beautiful selection of glassware, pottery, tiles, furniture, and textiles. You’ll also find elegant handcrafted jewelry (the shop has an excellent collection of wedding rings and offers a bridal registry) and stylish clothing. Fire Opal has a second location, on Harvard Street in Coolidge Corner, Brookline.

The Purple Cactus
674 Centre St.

This is the closest thing to fast food in JP. With an emphasis on fresh ingredients and vibrant flavors rather than heavy sauces, Purple Cactus offers a lighter, healthier interpretation of classic Mexican cuisine. The restaurant’s mantra is “big on flavor, low on fat.” Black beans are simmered without lard or additives, and the kitchen uses low-fat sour cream and lean steak in its dishes, which include an array of fabulous fajita wraps, rice and bean or shrimp burritos, excellent quesadillas, and a vegetable taco salad that comes with a zingy cilantro-lime vinaigrette. The superb guacamole is made daily. At prices averaging between $5.95 and $8.50, the Purple Cactus may represent the best dining value in all of JP.

City Feed and Supply
672 Centre St.

This grocery-café-deli is reminiscent of an old-fashioned general store, but with a modern twist. City Feed’s motto, “Buy Fresh, Buy Local,” emphasizes its commitment to sustainability and locally grown or prepared foods. A popular breakfast haunt among locals—particularly on weekends—City Feed offers excellent fair-trade coffee and a mouthwatering selection of sandwiches and baked goods. The produce is organic, the sodas, root beer, and sarsaparilla locally manufactured. The store offers the best selection of cheeses (most are from Vermont) in the neighborhood, as well as locally produced craft beers. City Feed often holds free food tastings and cooking demonstrations and actively supports local charities. A smaller City Feed can be found at 66 Boylston St., a short walk from the MBTA Orange Line’s Stony Brook station.

Centre Street Café
669A Centre St.

Specializing in locally raised food, this JP institution has a line outside every weekend during brunch hours. The restaurant’s crispy waffles with real maple syrup, pancakes du jour, and truck-stop breakfast (one large pancake, three organic eggs, home fries, and bacon or sausage) attract crowds from all over. Dinner is a quieter affair—in fact, cell phones are forbidden. As the restaurant notes, “Supper time is sacred.” The dinner menu offers several one-pot meals, as well as a number of dishes featuring locally produced beef and chicken and locally grown produce. The restaurant exudes a kind of hippie-retro vibe, and on the walls are a constantly changing selection of paintings by local artists, available for sale.

J. P. Licks
659 Centre St.

This original J. P. Licks ice cream shop (there are now 10 in and around Boston) could be the most popular place in JP. Referring to itself as an ice cream maker, coffee roaster, hip joint, and good neighbor, J. P. Licks offers ice cream in dozens of flavors, as well as nonfat smoothies, frappes, floats, egg creams, and sorbets and hard and soft yogurt. Each month the store offers seasonal specials. Not to be missed is the strawberry rhubarb ice cream available each June. The restaurant has a large fireplace that is put to good use during winter months. Outdoor tables make it an inviting place in warm weather. Everything made here is Kosher-certified.

JP Comics and Games
603 Centre St.

This store is a must for any gaming fanatic or comic book fan. It has a great selection of comics, graphic novels, board games, puzzles, magic, Pokémon, and Yu-Gi-Oh! It holds an open comic forum every other Saturday, Dungeons & Dragons encounters every Wednesday, and game nights every Thursday.

Ten Tables and TT Bar
597 Centre St.

This welcoming restaurant puts an emphasis on fresh ingredients from local purveyors, served in an intimate, elegant setting. Lights are dim and candlelight casts a glow over the tiny restaurant and adjoining bar. It serves wines from vineyards that practice organic or biodynamic winemaking and an interesting array of cocktails. The menu changes with the season, depending on what ingredients are available.

Tres Gatos
470 Centre St.

No ordinary tapas bar, Tres Gatos is the city’s “first full-service restaurant/book and music store,” according to its website. Formerly the book and music store Rhythm & Blues, Tres Gatos still sells books and music, and has a menu featuring classic tapas items, charcuterie, and appetizers, with an emphasis on local produce, fish, and meats. It also has a nice selection of classic and contemporary Spanish wines and hard-to-find brews. Based on the belief that “sharing good food, music, and books is essential to a happy life,” Tres Gatos has become enormously popular with locals. Seating varies from a bar to a large common table, several smaller standing bars, and a seasonal outdoor area.

Lucy Parsons Center
358A Centre St.

The Lucy Parsons Center is a collective of left-wing outreach efforts run by volunteers, offering space for community organizers and events such as a weekly radical film night and monthly vegan collective meetings. It supports itself by selling books and magazines, posters, bumper stickers, and T-shirts oriented to progressive politics. Open noon to 9 p.m. Monday through Friday and 1 to 7 p.m. Saturday and Sunday.

Canary Square
435 South Huntington Ave.

No matter what night of the week, this place is almost always packed. The environment is friendly, the food unpretentious but delicious, and the cocktail menu wildly inventive. Our favorite? The Centre Street, featuring bourbon, rosemary-orange syrup, fresh lemon juice, and a dash of ginger ale. Canary Square also offers nearly three dozen draft beers. Outdoor seating is available seasonally.

Off the Beaten Path

James’s Gate
5-11 McBride St.

Just off South Street and a short walk from JP Center, this Irish pub has a formal dining room as well as a pub. The façade replicates the exterior of St. James’s Gate Brewery in Dublin—the world’s oldest working brewery and home of Guinness stout since 1759. The walls are hung with work from local and regional artists. The setting is rustic and homey, emphasized by a menu heavy on comfort food (shepherd’s pie, “toastie” sandwiches, fish and chips). A massive stone fireplace in the center of the main wall welcomes visitors on a cold winter evening.

Canto 6
3346 Washington St.

Described by one fan as “pastry heaven,” this small bakery next to the Orange Line’s Green Street stop is easily one of the best in the city. Famous for its almond chocolate croissants, Canto Six also offers pear and goat cheese tarts, strawberry scones, and a shortbread cookie of the day. Of special note are the cannelés, small confections with a crème brûlée–like outer shell and a deep vanilla custard inside. The bakery takes its name from the sixth canto of Dante’s Inferno, which details the fate that awaits the gluttonous.

Doyle’s Café
3484 Washington St.

In business since 1882, this is the grand dame of the neighborhood’s eating establishments. Stepping inside is like taking a trip back in time. The walls are loaded with signs for now-defunct Boston breweries and all kinds of political memorabilia, including photos of nearly every Boston mayor, governor, senator, and representative of the last 100 years. One room is dedicated to former Boston mayor John F. Fitzgerald, the grandfather of President John F. Kennedy. A favorite watering hole among politicians, the café has figured prominently in a number of films, including Celtic Pride, Mystic River, and The Brink’s Job, as well as television shows like Boston Public. Home to one of New England’s largest selections of draft beers, Doyle’s was the first bar to put Samuel Adams Lager on tap.

Bella Luna and the Milky Way Lounge
The Brewery Complex, 284 Amory St.

Located in the former Haffenreffer brewery, this restaurant and music venue is one of the neighborhood’s most popular destinations. Bella Luna is famous for its pizzas and calzones and there is often a wait for a table, but the place also does a booming take-out and delivery business. An outdoor deck provides one of the best al fresco dining options in JP. The attached Milky Way Lounge offers an array of lively entertainment, ranging from trivia game nights to country line dancing, dyke nights, rock ’n’ roll bingo, and dance parties with Latin, reggae, and queer themes. The restaurant and lounge’s mission is to “create community through delicious food and beverages, art, and music; to be a gathering place where everyone feels comfortable and has fun.” Judging from the crowds, it’s clear they’re succeeding.

Ula Café
The Brewery Complex, 284 Amory St.

In the same complex as Bella Luna, this wonderful bakery–coffee shop carries fair-trade roasted coffee, espresso, and a wide selection of loose-leaf teas, as well as fresh salads and delicious pastries. The free WiFi attracts a lot of young professionals bearing laptops.

Getting there: The easiest way to get to JP is by taking the #39 bus from Copley Square to JP Center. The bus takes you down Huntington Avenue to South Huntington Avenue, which merges onto Centre Street. Or take the MBTA’s Orange Line to either the Jackson Square stop (for venues in Hyde Square) or the Green Street stop. The neighborhood is also within an easy bicycle ride; the Emerald Necklace bike path is one of Boston’s best.

Click on the points in the map above for more information on the places listed in our guide to the Jamaica Plain area.

Learn more about neighborhoods around Boston here. Check out our Jamaica Plain list on Foursquare for more neighborhood tips.