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A Jamaica Plain walking tour

Cobwebs on Centre Street scene in Jamaica Plain. Necee Regis for the Boston Globe/Necee Regis

JAMAICA PLAIN — There’s nothing ordinary about Jamaica Plain, or “JP” as it’s called, a dynamic Boston neighborhood located southwest of downtown.

The commercial district, along Centre and South streets, reflects Jamaica Plain’s eclectic community of artists, writers, musicians, activists, young families, and indie-business owners. Fine dining and casual restaurants serve foods of Cuba, Scotland, India, Lebanon, Cambodia, Japan, and other international fare. Boutiques sell everything from kitchen gadgets to funky vintage attire to one-of-a-kind artisan crafts.

Easily accessible by car, bus, bike, or MBTA, this historic neighborhood is part of Frederick Law Olmsted’s Emerald Necklace, a seven-mile series of contiguous parks designed in the late 19th century where residents and visitors enjoy biking, walking, and running.


On a recent chilly day, the atmosphere was warm in El Oriental de Cuba, the go-to place for authentic Cuban cuisine, and an anchor of the surrounding Hispanic community. You’ll hear as much Spanish as English spoken here, and the menu is printed in both languages. At the active take-out counter, owner Nobel Garcia joked with customers, showing photos on his smartphone as people picked up orders of roasted pork with black beans and rice, ropa vieja, and pressed Cuban sandwiches.

“I’ve been in Jamaica Plain almost 50 years,” said Garcia, who came from Cuba as a young boy. “It’s a wonderful neighborhood. I’ve seen a lot of changes — all for the better.”

Patrick Byrne, who was born and raised in Galway, Ireland, opened his antiques shop Cobwebs 22 years ago. This two-level shop (don’t miss the space downstairs) is crammed floor to ceiling with all manner of antiques, collectibles, jewelry, watches, chandeliers, armoires, paintings, and even fresh flowers.

“The great thing about Jamaica Plain is its community,” said Byrne. “The only reason I leave is to go to the movies.”

Steve Murakishi and his wife, Sue Stein, have been operating Fire Opal — selling “new American handmade” jewelry, clothing, and home goods — for 14 years. Known as a destination for unusual gifts made by US artisans, as well as clothing by young designers, Fire Opal is a staple on Centre Street.


“People like being in JP. There’s an investment in place,” said Murakishi. “There’s a good coexistence between folks in their 60s and folks in their 20s. I like to say that JP was settled by old hippies, and now the kids are here because they want a community.”

To experience a retro-hippie vibe, stop by the Centre Street Cafe, a neighborhood institution that served locally sourced food before it was fashionable. Locals stand in line for brunch that features organic eggs, sourdough French toast, and crispy raised waffles with fresh fruit and real maple syrup.

Caramelo Clothing Co. sells an eclectic collection of men’s wear, including classic and trendy jeans, ties, wallets, belts, sweaters, grooming accessories, and more. Curated by sisters Carolina and Tatiana Trejedor, the new-boutique-on-the-block (open since June) embraces its Jamaica Plain identity.

“The community is amazing. They tend to be risk takers in terms of dressing up,” said Carolina, adding, “Maybe it’s the artsy community. Our clients are extremely fun.”

Hat aficionados love Salmagundi, a full-service shop offering a selection of about 9,000 hats handpicked by the owners, the husband and wife team Andria Rapagnola and Jessen Fitzpatrick. They also offer a selection of accessories, including jewelry, handbags, dresses, ties, and gloves.


For bargain shopping, locals flock to Boomerangs, a thrift shop benefiting the AIDS Action Committee of Massachusetts. Sift through aisles of used clothing, as well as jewelry, handbags, furniture, toys, housewares, and more. The bargains continue one block away, at the Goodwill Store.

For all-vintage clothing, visit 40 South Street, a small space crammed floor to ceiling with jackets, dresses, sweater, boots, shoes, hats, and accessories, owned by Hilken Mancini.

“It’s not fancy vintage. It’s funky rock ’n’ roll vintage,” said Mancini.

Need a pick-me-up after shopping? Monumental Cupcakes serves a changing selection of cookies and cupcakes — some made with Belgian chocolate — as well as fruit smoothies, juice, coffee, tea, and vegan and gluten-free items. Or sit near the fireplace at J. P. Licks, located in a former Victorian fire house, and enjoy homemade ice cream, fair trade house-roasted coffee, hot chocolate, and baked goods.

The Haven, a restaurant on Perkins Street, serves Scottish fare with a New England twist.

“We serve a modern take on Scottish pub food,” said Joshua Loomis, who described his job as “henchman.” (“You can also refer to me as the bartender,” said Loomis.)

The Haven serves Scotland’s national dish, haggis, every evening (minced lamb offal with oats, onion, and spices) as well as items such as clam and sausage stew and vegetarian bubble and squeak. Live local music on certain weeknight evenings varies from traditional to British pop to singer-songwriter and jazz.

For American fare, Vee Vee is a cozy 30-seat restaurant owned by Dan and Kristen Valachovic. Its seasonally changing menu features creative bites, appetizers, and entrees, including gluten-free and vegan options. Red walls and wood tables add to the ambience, enhancing dishes such as Manchego potato croquettes, and Sardinian couscous with mushroom Bolognese.


Another local favorite is Tres Gatos, a tapas-style restaurant that also sells books and CDs. Sit at the bar or a large communal table to enjoy favorites such as patatas bravas, and lamb bocadillo.

In addition to dining and shopping venues, Jamaica Plain has many parks and places to enjoy nature. At the Arnold Arboretum, stroll through 281 acres of meadows, forest, and ponds, and see its collection of more than 15,000 plants. In the Hunnewell Building at the Arborway Gate you’ll find a visitors center, changing art exhibitions, and a horticultural library. Or join the bikers, joggers, and walkers circumnavigating the 1.5-mile path around Jamaica Pond, a pure glacial kettle hole. A boathouse provides facilities for sailing and rowing.

For a sense of Jamaica Plain’s rich history, dating to Colonial times, the Loring-Greenough House (circa 1760) features American furniture and decorative arts from the 18th through the early 20th centuries, and historic archival material. Or stroll through the 275-acre Forest Hills Cemetery, an open-air museum with Victorian architecture, a bronze angel created by sculptor Daniel Chester French, and burial sites of prominent Americans such as abolitionist William Lloyd Garrison, playwright Eugene O’Neill, and poets Anne Sexton and E. E. Cummings.


At the end of a busy day, you’ll find a pint and camaraderie at many establishments. Grab a seat at the bar at Brendan Behan Pub to sample one of 30 draft beers on tap.

“This place is the neighborhood living room for a lot of people,” said bartender Adam Wells.

At James’s Gate, an Irish pub, enjoy shepherd’s pie or fish and chips near the welcoming fireplace. Or step back in time at Doyle’s Cafe, an institution in town since 1882. Sample Irish brews Guinness and Smithwicks while dining on everything from chowder to burgers, meatloaf to pizza, and standards like broiled scallops, sauteed scrod, and steak tips.

It’s challenging to experience all that Jamaica Plain has to offer in one visit or even two. It’s a neighborhood made to return to again and again.

Necee Regis can be reached at neceeregis@gmail.com.