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The Best Outdoor Dining in 12 Boston Neighborhoods

By Scott Kearnan
June 10, 2014

Outdoor dining in Boston? There's plenty of it. But if you need to pick a destination for each neighborhood of the city, where would you go? Here are our top spots around town; tell us yours, and why, in the comments. 

  • Back Bay: Cafeteria

    People-watching on one of Boston's best (and most moneyed) shopping streets? Yes, please. The ample patio is a major draw at this Newbury Street spot, and it's filled mostly with thirtysomething crowds clinking martinis over elevated takes on familiar comfort foods. 

    Must-Order: This isn't your middle-school meatloaf. Cafeteria's version ($18) elevates the classic lunchroom staple to delicious effect, using grass-fed beef and a "spicy ketchup" glaze. 

    Insider Tip: Want eat out on Newbury on a decidedly non-Newbury budget? Order a burger at the bar (only) and they're just $5 all day, every day.  

    279 Newbury St.; 617-536-2233

  • Beacon Hill: The Hungry I

    Hidden amid the brownstones of Beacon Hill is this romantic secret garden, lined with brick and filled with elegant arrangements of antique hodgepodge.

    Must-Order: The French cuisine is top-notch, but we're especially in love with the venison au poivre noir ($39), sautéed flamed with cognac, sour cream and red wine. 

    Insider Tip: The small garden books up fast and early, so don't try your luck without a reservation. 

    71 Charles St.; 617-227-3524

  • Brighton: Devlin's

    Well-hidden from Washington Street is this huge rear patio, one of the only you'll find in Brighton. It has its own outdoor bar, babbling fountain—and several big-screen TVs. 

    Must-Order: Fair weather pairs well with a crispy flatbread ($14) topped with prosciutto, fig jam, caramelized onions, arugula and blue cheese. 

    Insider Tip: The patio also hosts live music, and unlike many other Brighton spots, it attracts a post-college (thirtysomething professionals) crowd.

    332 Washington St., Brighton; 617-779-8822

  • Charlestown: Pier 6 

    Holy harbor views. You can't beat the scenery from the roof deck at this Charlestown restaurant, which tends to boast a bumping weekend social scene. 

    Must-Order: The raw bar is a great go-to, but we also love the lobster chowder ($12) made with sherry, melted leeks, sweet potato and bacon.

    Insider Tip: Enjoy the same views from the inside by booking the private dining room with three walls of windows and a communal dining table for 14.

    1 Eighth St., Charlestown; 617-337-0054

  • Dorchester: Ashmont Grill

    Outdoor dining options are at a premium in Dorchester, and this spacious patio feels far away from the urban surroundings. Head here for accessible but elevated comfort food and cocktails on a warm summer night.

    Must-Order: Chef-owner Chris Douglass has been beloved since his days at the South End's fine-dining destination Icarus. But we're especially partial to his pasta, so the rigatoni Bolognese ($18) with a pork, beef and veal meat sauce is a must. 

    Insider Tip: If you can play half-day hookie, start your weekend early here. The restaurant offers lunch on Fridays only from 11 AM-3 PM.

    555 Talbot Ave., Dorchester; 617-825-4300

  • Downtown: Battery Park

    Cool and cloistered, yet able to hold 100, Battery Park's patio is a former alley reimagined as a vertical garden-covered haven for after-work cocktails and better-than-average sports-pub fare. 

    Must-Order: The tangy and tantalizing chicken wings ($10) deep-fried and tossed in a honey-cayenne sauce. 

    Insider Tip: During the summer, Island Creek Oyster Farm sets up a pop-up raw bar on the patio on Thursday from 6-9 PM. Stop by and slurp away.

    33 Batterymarch St.; 617-350-7275

  • Fenway: Sweet Cheeks Q

    If amazing barbecue wasn't enough to lure you to this Fenway-side favorite from Top Chef runner-up Tiffani Faison, the awesome beer garden should be. 

    Must-Order: Fill a Fat Cheeks Tray ($26) with pulled pork, brisket and ribs, then round it out with broccoli casserole and one of the best mac 'n' cheese sides around. Trust us. 

    Insider Tip: The beer garden has a retractable roof. So even if a Sox game is rained out, supper won't be. 

    1381 Boylston St.; 617-266-1300

  • Jamaica Plain: Tres Gatos

    Eating at this fabulous tapas hideaway feels like dining in someone's living room, so naturally, the small patio feels like dining on someone's front lawn. And yes, that's charming. 

    Must-Order: We're drunk in love with the mussel escabeche ($6), marinated in sherry vinegar with pickled celery.

    Insider Tip: The dinner-party feel is accentuated by regular live music and the used book and vinyl shop in back. Grab a glass of wine and rifle through some, like you're digging through your host's LP collection.  

    470 Centre St., Jamaica Plain; 617-477-4851

  • Roslindale: Sophia's Grotto

    For many, Boston's Roslindale neighborhood already feels like undiscovered country. So consider Sophia's Grotto a hidden gem within a jewel. The intimate Mediterranean eatery has an alleyside patio ringed with greenery.

    Must-Order: The rib-sticking Italian menu includes a stellar farfalle al pesto ($15.95), a heaping bowl of butterfly pasta in a thick, creamy pesto sauce laden with pignoli nuts, sun-dried tomatoes and garlic. 

    Insider Tip: Sophia's also serves a great brunch, including an antipasto ($8.95): herb-garlic sour cream and caper spread with tomatoes, red onions, hard-boiled eggs, herb and nut goat cheese, fresh fruit and toast. 

    22 Birch St., Roslindale; 617-323-4595

  • Photo by: Chip Nestor

    Seaport District: Legal Harborside

    The Seaport has become a definite dining destination, and plenty are flocking to the rooftop of this Legal outpost, an energetic scene that helped reinvigorate the brand. 

    Must-Order: Our bucket list of 30 Things You Must Eat & Drink This Summer includes the tempura lobster roll (market price) with avocado, tobiko, teriyaki and spicy mayo.

    Insider Tip: The rooftop doesn't take reservations, so get there early and stake out your sunset view before the after-work crowds descend en masse. 

    270 Northern Ave.; 617-477-2900

  • South Boston: Barlow's

    Upscale American is the order of the day at this South Boston spot, which tends to go undiscovered except by locals. The ample patio is a nice place to catch some rays away from the denser, bar-packed parts of Southie. 

    Must-Order: Spice up your life with Manny's BBQ Meatloaf ($16) served with bacon, corn on the cob and jalapeño mac 'n' cheese.

    Insider Tip: There's $3 validated parking, but Barlow's is also a stop on the Southie Shuttle, which offers free service among participating restaurants.

    241 A St., South Boston; 617-338-2142

  • South End: B&G Oysters

    The South End is full of sidewalk patios. But when you're looking for something more private, we love this intimate, sunken patio behind Barbara Lynch's South End seafood pearl. Shuck on over.

    Must-Order: For its sheer consistency, the lobster roll ($29) is a perennial go-to, loaded with chunks of Maine lobster on a toasted roll and served with fries and butter pickles.

    Insider Tip: Starting this week, $1 from every order of fried calamari benefits the Barbara Lynch Foundation, which supports life-skills-building resources for disadvantaged youth. Just in case you needed an excuse to order.

    550 Tremont St.; 617-423-0550

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Places Mentioned

Sweet Cheeks Q

Barbecue • Fenway/Kenmore

Food25 Decor22 Service23 Cost$29
 
 
 
B&G Oysters

Seafood • South End

Food27 Decor22 Service24 Cost$47
 
 
 
Legal Harborside

Seafood • Seaport District

Food25 Decor23 Service23 Cost$36
 
 
 
Cafeteria Boston

American • Back Bay

Food22 Decor22 Service21 Cost$24
 
 
 
Sophia's Grotto

Mediterranean • Roslindale

Food22 Decor21 Service23 Cost$29
 
 
 
The Hungry I

French • Beacon Hill

Food24 Decor23 Service22 Cost$57
 
 
 
Ashmont Grill

American • Dorchester

Food24 Decor22 Service22 Cost$27
 
 
 
 
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