Gear Up For Boston Summer With These Bay State Bars, Restaurants, And Events

Renowned worldwide for its historic significance and wealth of world-class universities, Boston draws tourists from all corners of the globe throughout the year—but for longtime locals and new visitors alike, there’s no better time to be in the city than June. Fresh off the heels of Memorial Day, the month kicks off with a wide array of outdoor events and attractions, with no shortage of charming bars and restaurants to explore along the way. With summer just a few weeks away, the following venues offer an opportunity to explore Boston at its finest, showcasing the splendor of the Bay State capital just before the summer heat reaches its peak.

Catch a Jaw-Dropping Cliff Diving Performance in the Seaport

First launched in 2009, the Red Bull Cliff Diving World Series showcases some of the most exhilarating acts of acrobatics on the planet—and fortunately for Bay State residents, this year’s jaw-dropping festivities take place right on Boston Harbor. On June 3rd, Bostonians are welcome to swing the ICA and enjoy the show, with each of the 24 participants dropping more than twenty meters into the sparkling water below. To keep the thrills going after the initial plunge, be sure to catch one of the other performances within the series, with future dives taking place from June to November in dazzling destinations including Italy, Japan, and New Zealand.

Enjoy Fine Dining to the Tune of Live Music

While June brings the occasional rainstorm to the streets of Boston, there’s no shortage of cozy indoor venues offering top-tier cuisine and live music to take your mind off of the gloomy weather. In the heart of the South End, The Beehive has been one of Boston’s top destinations for jazz, blues, and funk since 2007, serving up crispy arancini, grilled garlic shrimp, and spicy sausage-loaded fusilli pasta in a gorgeous crystal chandelier-clad space. For Seaport residents, Grace by Nia is a recent arrival to the district’s dining scene, launched at the behest of local community leader Nia Grace. Upon arrival, guests can snag high-end Southern classics like gumbo ceviche, Maryland hot crab dip, and Cajun jambalaya, all to the tune of stellar R&B, jazz, and soul performances.

Embark on a Craft Beer Crawl Across the Seaport

Boston’s sparkling Seaport District draws longtime residents and new arrivals alike, all convening to take full advantage of the neighborhood’s incredible drinking and dining scene. For beer fans in particular, the neighborhood is packed with a surprisingly high concentration of breweries and beer gardens, with Cisco Brewers Seaport serving as one of the city’s hottest summer spots. Open from April to October, this seasonal popup is home to fresh seafood, live music, and Nantucket favorites like Whale’s Tale Pale Ale, while neighboring venues like Trillium Fort Point—a vibrant space complete with an open-air rooftop terrace—and the NEIPA pioneer Harpoon Brewery are located just a short walk away.

Discover the North End’s Top Trattorias

Historic churches, storied pastry shops, and gorgeous waterfront views are all awaiting visitors in Boston’s North End, an iconic district that’s earned nationwide acclaim for its rich Italian-American heritage. To kick off your crawl, the polished Bricco is a local favorite thanks to their top-quality espresso martinis, providing diners with some much-needed energy alongside savory dishes like frittura mista, zucchini flowers, and veal ossobuco. After a few drinks, there’s no shortage of other stellar trattorias found within walking distance—Mamma Maria has earned abundant acclaim for their refined Mediterranean cuisine crafted with local New England ingredients, while Strega is perfect for keeping the drinks flowing, equipped with dazzling cocktail trees that pair perfectly with an order of fried calamari.

Visit the Encore Boston Harbor’s Newest Cocktail Lounge

Officially opened in 2019, the massive Encore Boston Harbor has become one of the region’s top destinations for a wild night on the town, with massive suites, a world-class casino, and more than ten drinking and dining concepts—and this top-tier entertainment center is soaring to even greater heights with the launch of Rare Lounge. Located just a few steps away from the award-winning Rare Steakhouse, this newly-opened venue is home to a wide array of savory dishes, with options like wagyu beef pigs in a blanket and truffle grilled cheese crafted by Executive Chef Megan Vaughan—and this upscale space is no stranger to high-end cocktails either, with the passionfruit liqueur and pink peppercorn-loaded Calico Skies standing out as a particular menu highlight.

Set Sail Along The Boston Harbor Islands

With roughly 30 different destinations scattered just past the Bay State shoreline, Boston’s Harbor Islands showcase an oft-unexplored side of the Massachusetts capital. For those hoping to set foot on one of these underrated gems, a trip with Boston Harbor Now offers quick access to some of the region’s top destinations, with voyages to Peddocks Island, Spectacle Island, and a wealth of other seaside spots open for booking. As an added bonus, Boston Harbor Now also offers regular events throughout the year, with Juneteenth guided tours and the LGBTQ+-focused Pride in the Park serving as two particularly interesting June outings.

Experience Belmont’s Booming Beer Scene

In need of some top-tier European ale to beat the June heat? Skip out on that flight to Munich and hop on the Fitchburg Line to find Trinktisch, a German-style beer hall that’s equipped with more than thirty different brews for guests to sample. While beer options range from New England DIPAs to fruited sours to Bavarian Weizenbock, there’s a wealth of hearty Central European dishes up for grabs as well, with currywurst and Jägerspätzle both serving as two can’t-miss plates. If you haven’t quite had your fill of beer after a visit, the iconic Craft Beer Cellar is just a few steps away, providing visitors with more than 1,000 bottles to choose from.

Immerse Yourself in Boston’s Greek Dining Scene

Boston is home to a diverse food scene that represents all corners of the globe, and the flavors of the Aegean are no exception. For a deep dive into the complexities of Greek cuisine in liquid form, Back Bay’s Krasi offers several hundred different wines sourced from all across the nation, all accompanied by a lengthy food menu that spans from grilled sea bream to filet mignon tartare. Further east in the Seaport, Committee has been slinging up ultra-flavorful cocktails and top-quality meze since 2015, while the fast-casual Greco dishes out hearty gyros all across the city, with locations in Back Bay, Downtown Crossing, and the Seaport.

Celebrate the Return of Summer on the Boston Waterfront

Afternoon tea, a 60-foot lap pool, and a eucalyptus-infused steam room are just a few of the year-round amenities awaiting guests at the ultra-luxurious Boston Harbor Hotel, while the warmer months bring a particularly exciting celebration in the form of the Summer in the City Series. This annual celebration kicks off its 24th iteration this year, drawing crowds to Rowes Wharf Sea Grille to enjoy fresh seafood, complex cocktails, and live music performed atop a floating barge. While this year’s grand debut takes place on June 8th, the festivities continue until August 25th, providing plenty of time to bask in the beauty of Boston’s most stunning harborside hotel.

Catch the Big Game at Boston’s Hottest Sports Bars

Equipped with a roster of all-star sports teams and the nation’s oldest active MLB ballpark, Massachusetts is a veritable paradise for sports aficionados—and of course, there’s no shortage of vibrant bars that have fully embraced the city’s legacy. For those north of the Charles, The Phoenix Landing has been a top spot for Cambridge sports fans for more than 25 years, while Fenway is home to one of Boston’s finest entertainment venues in the form of Game On!, a sprawling space that comes complete with 30 HDTVs, local craft beer, and even their own indoor batting cage. And when it comes to cocktails, West End Johnnie’s has mastered the art of mixology, celebrating the spine-tingling 2023 Celtics season with a wealth of Bushmills-loaded favorites ranging from the Iced Irish to Timeout Whiskey Lemonade.