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Best Outdoor Dining in Boston

With a weekend high of 75 degrees and plenty of sunshine in the forecast, patio season is officially upon us! Not only is outdoor dining a great way to get outside and enjoy the benefits of the outdoors, but it’s also a covid-safe way to gather in small groups. Covid-19 transmission is less likely outdoors with open ventilation, and fully vaccinated people may now conduct outdoor activities maskless, except in crowded venues.

From makeshift patios in parking lots to distancing pre-pandemic outdoor seating, restaurants in Boston are looking to accommodate as many people as safely possible this summer. The restaurant business has been hit hard during the pandemic, so rest easy in knowing that by eating outdoors at these fantastic restaurants, you are supporting Boston businesses.

For a taste of normalcy alongside incredible food, the restaurants below are tried-and-true Boston favorites.

1) Brunch

Bootleg Special

South End

400 Tremont Street

Boston, MA

Regular brunch has gotten so boring, don’t you think? Bootleg Special is here to alleviate your Boring Brunch Woes. This Cajun-inspired seafood tapas bar shatters any glass ceilings one may have imposed on the brunch world. From street corn to cajun “boils” to fluffy souffle pancakes, Bootleg Special has it all. The imaginative food is almost outshone by the incredibly fun cocktails. For brunch, enjoy the magically delicious “Leprechaun Trap,” made with Lucky Charms cereal. The Bootleg Special has added outdoor dining options as a result of the pandemic, so make sure to snag a reservation for a beautiful day before they all get taken!

2) Rainy Day

Mare Oyster Bar

North End

223 Hanover Street, 3 Mechanic Street

Boston, MA

This impossibly cool oyster bar is the new place for hip young adults to see and be seen. Sleek and sophisticated, their outdoor patio has a retractable roof; rainy days don’t have to ruin your social life! Ditching the North End’s heavy focus on Italian, Mare Oyster Bar is seafood-centered, as the name implies. Run by DePasquale Ventures, owners of other trendy North End staples such as Bricco and Trattoria il Panino, Mare is no exception to Frank DePasquale’s history of restaurant excellence, even holding Wine Spectator’s Award of Excellence.

3) People-watching

Stephanies on Newbury

Back Bay

190 Newbury Street

Boston, MA

Want to support a Boston institution while getting your daily dose of people-watching in? Look no farther than Stephanie’s on Newbury. In the heart of the Back Bay on the busy corner of Newbury and Exeter, Stephanies on Newbury fosters a “casual but elegant” dining experience. Light bites such as avocado toast and more filling dishes like rigatoni bolognese means Stephanie’s has something for everyone, for every time of day. Be sure to make a reservation online before going, as Stephanie’s is no newbie to the patio game, and there can be incredibly long waits.

4) Rooftop

Lookout Rooftop Bar


70 Sleeper Street

Boston, MA

With Seaport being the fastest-growing part of Boston as of 2017, it would be a shame not to include a Seaport rooftop bar. Chic, sleek, and sophisticated, the Lookout Rooftop Bar is atop the Envoy Hotel. Incredible views of the city skyline and harbor make the $17+ cocktails easier to swallow (careful, though, they taste so good you won’t be able to stop drinking them). Fireplaces and a sheltered center bar area means that the rooftop is perfectly equipped for surprise summer showers and cold snaps.

5) Casual

Thinking Cup

Multiple Locations

While a full outdoor dining experience can be great, getting a reservation in Boston for outdoor seating on a nice day can be like trying to find a needle in a haystack. For a casual but incredibly delicious, no-reservation-needed café experience, Thinking Cup is the place to go. Incredible coffees, breakfast and bakery options, and killer sandwiches, the Thinking Cup is the perfect place to settle in with a nice book on a gorgeous day. A Back Bay, Boston Common, and North End location means there’s plenty of coffee, and seating, to go around.

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