The Best & Worst of Summer Dining in Boston

By Scott Kearnan  |  June 3, 2014

Boston blooms in the summer. Patio seats come out, sleeves come off, and food tastes better (because we're in really, really good moods). Still, there are a few annoyances: like bad beer that kills our Fenway game-day buzz, and sudden downpours that rain on our rooftop dining plans. Here, a few of the best and worst parts of summer dining in Boston - with some solutions to keep the second at bay. 

And be sure to check out our new Best Summer Ever page - we'll be bringing you the season's best eating and drinking all the way through Labor Day.

  • Fenway nights

    Best: An excuse to gorge on hot dogs and beer on a breezy summer night at Fenway. Put us in, coach!

    Worst: Hot dogs that taste like a shoe's rubber insole, and beer that tastes like what happens after you drink a lot of beer.

    Solution: Brush up on this guide to Fenway Park dining, which includes a look at where to get the best grub inside the stadium (like the new Tasty Burger outpost) and outside (like Basho, a nearby sushi spot that won't attract throngs as thick and drunk as those that hit up the local sports bars).  

  • Credit: Gary Gilbert

    College break

    Best: Grabbing the newly empty seats at campus-area restaurants now that the students have gone home for the summer. 

    Worst: Having absolutely no idea where to go, since you've spent the other nine months of the year avoiding anywhere with loud coed crowds. 

    Solution: Check out this breakdown of some of our top picks by college 'hood, like Church near Simmons College and The Elephant Walk by BU. 

  • Ice cream

    Best: Licking a yummy, cold cone on a sweaty, hot day. I scream, you scream, we all scream for - well, you know the drill.

    Worst: Watching empty-handed from the sidelines as other people enjoy a sweet treat. Because the following people don't scream for (traditional) ice cream: dieters, vegans, the lactose-intolerant. 

    Solution: Think outside the typical ice cream stand and check out boutique-y spots with nondairy options. 3 Scoops Cafe specializes in handmade, micro-batch, nondairy alternatives (including low-calorie "Skinny Dip" options). And FoMu makes vegan and lactose-free ice cream using a coconut base sweetened with organic sugar and agave. 

  • SoWa Open Market

    Best: Browsing the awesome artisans, farmer's market and lot full of fantastic food trucks, inevitably eating (and spending) just a little bit more than your weekly budget should allow. Whoops. 

    Worst: During peak crowd hours the truck lines can get a little out of hand - especially when you're just searching for a soda to slake your summertime thirst. 

    Solution: First take a peek at our guide to great SoWa food truck eats. If the waits get unwieldy, take note of a few South End favorites that are within close walking distance, so you'll be able to resume your market stroll shortly: great brasserie Gaslight, storied Irish pub J.J. Foley's and Asian go-to Myers + Chang are all nearby. 

  • Day drinking

    Best: Spending the day kicking back with friends and drinking something boozy, which feels a lot more fun when you're doing it on a sunny summer day than when it's snowing out and dark by 5. Y'know? 

    Worst: Getting stuck in "I'll have the seasonal" mode, or a rosé rut. 

    Solution: Get playful with adult takes on childhood favorites. Papagayo offers tantalizing tequila sno-cones in four different flavors. Kitschy Kendall Square hangout The Friendly Toast and JP burger bar Grass Fed both make boozy milkshakes - like the latter's Banana's Foster Parent with vanilla ice cream, banana, dark rum and whipped cream.

  • Credit: Chip Nestor

    Rooftop season

    Best: Catching some rays at a rooftop restaurant. 

    Worst: Soaking up the rain when those blue skies darken without warning. We just got our food!

    Solution: Pick a spot with a retractable roof or awning, like Legal Harborside or Ristorante Fiore. For other rooftop ideas, check out this list of top (literally) spots. 

  • Day trips

    Best: Piling into a car and hitting the road for a day trip spent discovering a whole new food scene, and maybe even making a Cape weekend out of it. (You know, at these places.) 

    Worst: Bourne Bridge traffic. No. Just...not today, guys. 

    Solution: South isn't the only direction on the map, you know. Avoid Cape Cod melee by hitting the North Shore (here are 10 reasons why Salem is a magical dining scene) or nearby Portsmouth, New Hampshire, a seaport charmer

  • City barbecues

    Best: Ribs. Brisket. Sauce. Wings. Sauce. Pulled pork. Did we say sauce? 

    Worst: That's, like, a lot of work, and after a couple beers you're really not paying attention to the grill the way you should be. 

    Solution: Obviously you can let the chefs do the work at great 'cue joints like Tiffani Faison's Sweet Cheeks Q, pictured, or Blue Ribbon BBQ, a longtime favorite worth the quick trip to Newton. But one of our favorite finds is Big Pig BBQ, a catering-only company that focuses on backyard barbecues, offering a choose-your-own-adventure type of online ordering system. You pick a package big enough to feed a farm, like the Finger Lickin' BBQ ($20/person) with ribs and chicken wings, plus creative salads and sides. You can even add extras like photography and DJ services. Summa-summa-summatime.