Top Outdoor Dining Restaurants in Boston

Viva la summer! Although we love to travel around the world, it’s always hard for us to leave New England in the summer time due to our gorgeous weather here. Warm breezes, longer days of summer sun, beautiful flowers, and an energetic buzz in the air make us squeal with delight!

Here are some of our favorite places to eat al fresco, top outdoor dining in Boston, Cambridge, and Somerville:



Grendel’s Den
Harvard Square, Cambridge


Historical Winthrop Park in Harvard Square is the country’s longest continuous park — started in the 1600’s, it was once Newtowne Market, a farmer’s market, and you can still see the sign there today. The summer is an especially wonderful time to grab a seat here because school’s out for the summer, and that means there are somewhat fewer students so that means more seats for the locals! Grendel’s Den serves up delicious and varied fare year-round. Second generation owner Kari has put her stamp on the menu, offering some healthier and tasty alternatives to traditional bar food. And you’ll be able to listen to some cool tunes, too!



Posto Somerville
Davis Square, Somerville


Well, Sam and I are slightly biased because this was the restaurant where we had our first date. Nothing can keep us away from a sidewalk pizza cafe. Posto, meaning “our place” in Italian definitely has that ‘homemade’ vibe, but it is also upscale so don’t expect cheap eats. Grab a sidewalk seat, and you’ll have a front row seat to the colorful characters strolling down Elm. Their seafood and chicken is also top-notch; you can’t go wrong with their fresh menu.



South End, Boston


Probably our favorite al fresco dining spot in Boston, Picco has a shaded front patio and is now taking limited reservations. Our go-to meal there is to split the arugula salad and the a large wood-fired margherita pizza with ricotta cheese and extra garlic. Oh, but we save room for a sundae for dessert including fudge sauce and delicious whipped cream, not too sweet! Afterwards, grab a show at nearby Calderwood Pavilion or stroll down to Gifted for a fun gift such as a Jerry Garcia coaster, some new jewelry, or a thoughtful card.



Whole Heart Provisions
Central Square, Cambridge


On a more casual note, we love the patio at Whole Heart Provisions right on Mass. Ave. in Central Square (where we meet for our Central Square Food Tour on Saturdays.) Having lived in Central Square for a decade, we can decidedly say that the weekend vibe is very different from the weekday vibe, and this section of the Square is somewhat less crowded so there’s always a table and a relaxed feel. Another great patio is across the street at Naco Taco. And there’s always delicious coffee at Darwin’s or bubble tea at Abide to soak up along with the sun.



Union Square, Somerville


We love a good outdoor market; and Bow Market in Union Square, Somerville absolutely shines in the warm weather. With limited covered seating, this market was definitely made for the summer months. There are a number of food stands that are absolutely delicious in Bow Market, and we visit it on our Union Square Somerville Food Tour. The bulgogi is so sweet and delicious in the Perillas rice bowls, and you can order a soft boiled egg on top — such a treat! Next door they serve incredible empanadas and delicious pierogies. Finish the afternoon with a chocolate treat or wander over to Gracie’s for a torched marshmallow fluff cone.



Fiore Bakery
Jamaica Plain, Boston


One of our favorite patios in Boston is at Fiore’s in Jamaica Plain, which we visit on our Jamaica Plain Food Tour and Jamaica Plain Vegan Chocolate Tour. Hurry, though, because spots can fill up in this popular spot. Save room for dessert, as they have incredible and not “too sweet” items like our favorite their peanut butter boomerang (chocolate covered) and old stand-bys like their Boston Cream Pie and other local favorites.



Cafe Beatrice
Allston, Boston


We dig urban pop-ups, and the transformation in Allston has been really impressive. This area of town has a rotating line-up of top chefs making a personal mark on the space, from wood-fired pizza to a new cafe. Chef Will Gilson even wallpapered the space himself, a spot he named for his daughter. Yes, we like avocado toast. And it feels breezy and fresh inside.



Cambridge Common
Porter Square, Cambridge


Bottoms up! From their famous bloody mary’s to ice cold lemonade, Cambridge Common is a front row seat near Harvard Law School to the urban Cambridge scene. Their broad wooden tables are comfortable and the perfect spot for your circle of friends to rehash the work week. If you’re still hungry afterwards, nearby Berryline has the best tart yogurt with fruit in town or indulge your sweet tooth at Honeycomb Creamery next door.



Commonwealth Kitchen
Kendall Square, Cambridge


Man, these folks know food. Created by former Executive Chef “Nookie” Postal of the Red Sox, you never know what will grace their menu from fried chicken sandwiches to out of this world salads and wacky ice cream flavors (try the banana cream pudding). With a bit of a Southern twist, their menu is always changing and is sure to please. Go kayaking next door after your meal, or join our Kendall Square Food Tour on Saturday afternoon as we stop here for a sweet treat on our urban walking adventure which is all about innovation!



Evoo and Za
Kendall Square, Cambridge


These sister restaurants have something for everyone, and their patio is second to none. Peeking up from the potted plants by the entrance, you’ll see some fresh herbs which is indicative of the farm to table approach and care they take at this phenomenal spot in Kendall Square. We love visiting them on our Kendall Square Food Tour, and you’ll enjoy eating delicious and fresh eats while summering on their patio weekday and weekend.


So if you can’t get to Paris this summer, no worries, don your sunglasses and grab a wicker chair on the sidewalk. People watch your little heart out in our fair city by the Harbor!


Off The Beaten Path Food Tours is a really fun summer activity. Our food tours and chocolate tours are both a history lesson and an urban walking adventure of great value! Please check out our Tour Calendar and book your experience today.

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