Rediscovering Jamaica Plain

When I recently brought an out-of-town friend to Jamaica Plain after a morning spent in Beacon Hill, she turned to me and said, “You didn’t tell me we were road-tripping to Portland.” She didn’t specify Maine or Oregon, but she didn’t have to: The point was clear. Like so many visitors, she associated Boston with cobblestones and Top-Siders.

[sidebar]To the uninitiated, the five-mile journey from the State House to J.P.’s Centre Street — less than 20 minutes from Downtown Crossing via the Orange Line — feels as vast as a cross-country road trip. Jamaica Plain’s combination of artists, professionals, and young families gives way to a bohemian blend of food, shops, and nightlife that fills many niches otherwise underserved in Boston. Here’s how to take it all in.

MORNING
Stop by for a $13.95 brunch at the cozy Bon Savor bistro (605 Centre St., 617-971-0000,bonsavor.com), which offers made-to-order omelets, freshly baked croissants, French press coffee, and champagne. Or try the new breakfast pizza at the always-reliable Dogwood Café (3712 Washington St., 617-522-7997, dogwoodcafe.com) — a satisfying pie topped with scrambled eggs, Applewood-smoked bacon, home fries, mozzarella, and breakfast sausage.
Then shop your way through some of Boston’s best vintage and thrift stores. Dame (68 South St., 617-935-6971, jpdame.com) stocks mint-condition party dresses from the ’60s and back-in-vogue ’80s Ferragamo flats, while 40 South Street (617-522-5066, fortysouthst.com) has a plentiful collection of vintage Levis. The haphazard selection at Boomerangs (716 Centre St., 617-524-5120, shopboomerangs.com), meanwhile, could consume the entire day: From used books (including pristine recent hardcovers) to jewelry, ’70s-era toys, and the sorts of delicate dishes and teacups that inspire Anthropologie knockoffs, you’ll find much more than clothing here.

AFTERNOON
There are few better places to while away a warm day than J.P. Before transportation turned the neighborhood into a 19th-century streetcar suburb, its wooded hills were sprinkled with well-to-do country estates and farms. The Arnold Arboretum (125 Arborway, 617-524-1718, arboretum.harvard.edu) is a modern-day reminder of that bucolic past. These 265 acres, owned by Harvard University, boast a world-renowned collection of flowering trees and plants. To kick off an active afternoon, take a leisurely bike ride along the arboretum’s two-mile main road, then pedal a half mile farther to the rowboat-dotted shores of Jamaica Pond (rentals, $10 per hour; Jamaica Way, 617-522-5061, jamaicapond.com). If you’re more in the mood for running or strolling, head for the nearby Forest Hills Cemetery (95 Forest Hills Ave., 617-524-0128, foresthillscemetery.com). This destination will especially impress bibliophiles: The literary luminaries buried here include e.e. cummings, Anne Sexton, and Eugene O’Neill, but the cemetery also serves as an impressive 275-acre green space and sculpture park with breathtaking examples of Victorian architecture and monuments.

EVENING
Make a dinner date with James’s Gate (5–11 McBride St., 617-983-2000, jamessgate.com) and order the scrumptious shepherd’s pie and house-made wild mushroom ravioli, all the tastier enjoyed on the quiet patio this time of year. If you’re looking for a lively night out, try Bella Luna Restaurant and the Milky Way Lounge (284 Amory St., 617-524-6060, milkywayjp.com) for one-stop dining, music, and dancing. Tucked away in the factory-chic Brewery complex, this J.P. institution packs its calendar with many events, such as salsa and merengue nights every Saturday at 9 p.m. To gear up, order Bella Luna’s “Better Than Your Mama’s Meatballs,” perfectly paired with Parmesan linguini. And there’s no better way to cool off after dancing than with a scoop or two at the original location of Boston ice cream institution J.P. Licks (659 Centre St., 617-524-6740, jplicks.com), open until midnight.