ICA
Photograph: Iwan Baan | The Institute of Contemporary Art/Boston
Photograph: Iwan Baan

The best things to do in Boston this weekend: May 2-4

There's an '80s synch pop icon at Big Night Live, plenty of Kentucky Derby celebrations, the Grand Tasting of a huge food fest, an annual May Fair, and more

Cheryl Fenton
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Whether you want to rock out to Alison Moyet's British sound, hit Harvard Square for some May mayhem, go to the final Grand Tasting of the Big Queer FoodFest (complete with a drag show), or don a fascinator as you head to the races (sort of), there's certainly no shortage of things to do in Boston. We have some ideas for the best things to do this weekend in Boston.

RECOMMENDED: Full guide to the best things to do in Boston

Things to do in Boston this weekend

  • LGBTQ+
  • Downtown

The first of its kind, the Big Queer Food Fest is the largest celebration of the LGBTQIA+ culinary community in Boston. The week-long festival celebrates LGBTQIA+ chefs, winemakers, distillers, brewers, authors, and purveyors from Boston and beyond by featuring culinary and community happenings throughout the city. Events include chef dinners, queer parties, happy hours, and discussions with chefs and authors, such as the Queer Beer Meet up at Dorchester Brewing Co., "Girl peas! Why Queer Food Matters," the Big Queer Tea Party, and "Serving the Look: Queer Identity and Food Photography and Storytelling." The full week's schedule can be found here, kicking off with the Opening Night Sizzle at Sweet Cheeks Q on April 28 and culminating in a weekend of Grand Tasting days on May 3 and 4 from 1pm to 4pm at High Street Market (don't miss Sunday for a special drag queen edition).


  • Things to do
  • Boston

With Derby Day race excitement galloping into the city, Trifecta at Four Seasons Hotel One Dalton Street hosts its Kentucky Derby Tea full of Southern charm, signature cocktails, and steaming cups of teas. The hotel's beloved Afternoon Tea goes Derby on May 3 with bourbon cocktails, race day attire (with prizes for best hat), live music, and more. Serving up classic J'enwey tea and pastries alongside cocktails from Michter's Whiskey including Thai Basil Julep and Pimm's Cup, Trifecta will offer three seatings (11am, 12:45pm and 2:30pm). In the evening, specialty cocktails will be available to enjoy alongside screening of the race. Reservations via OpenTable.

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  • Things to do
  • Theater District

If they want to go to see one of today’s most influential motivational experts, a New York Times best-selling author, and a podcast host, then let them (and join them!). Following incredible fan demand for her first round of shows, Mel Robbins has extended her inaugural global tour  — Let Them The Tour – adding a second and third show in Boston. One of the most followed and sought after experts in mindset, behavior change, and life improvement, Robbin begins her tour with a three-night stint at the Boch Center Wang Theatre in Boston from May 1-3. 

  • Music
  • West End

Noted for her powerful bluesy contralto voice and her place at the frontwoman for synth pop new wave British band Yazoo, Alison Moyet hits the stage solo at Big Night Live for a show on May 3 at 6pm. While she'll hit a few of the famous hits from the band's two albums, Upstairs at Eric's and You and Me Both (yes, you'll more than likely hear "Only You", "Don't Go", "Situation" and "Nobody's Diary"), her distinctive, passionate voice will also wrap itself around her own music, including songs from Key, her 10th studio album - a collection of 16 reworked singles and deep cuts released to celebrate 40 years as a solo artist.

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  • Things to do
  • Bay Village

Don your finest fascinators and fedoras and head over the Revere Hotel for Derby Day on May 3. This exclusive party in the Lantern Lounge, a sleek and intimate space next to Rooftop@Revere, is from 4-8pm high high above the city on Boston’s largest rooftop. Your ticket includes two Woodford Reserve Mint Juleps (the hotel’s spirited nod to the famed Derby drink) and a curated selection of small bites from their all-new summer menu. There will be live coverage of the big race on the big screen, and a hat contest with a grand prize of an overnight stay at Revere Hotel for the most fabulous Derby Day look.  

  • Chinatown

On Wednesday we wear pink. And April 29 to May 4, we visit the Emerson Colonial Theatre to see Mean Girls, a hilarious hit musical from an award-winning creative team, including book writer Tina Fey (“30 Rock”), composer Jeff Richmond (“Unbreakable Kimmy Schmidt”), lyricist Nell Benjamin (Legally Blonde) and original director and choreographer Casey Nicholaw (The Book of Mormon). Cady Heron may have grown up on an African savanna, but nothing prepared her for the vicious ways of her strange new home: suburban Illinois. Soon, this naïve newbie falls prey to a trio of lionized frenemies led by the charming but ruthless Regina George. But when Cady devises a plan to end Regina’s reign, she learns the hard way that you can’t cross a Queen Bee without getting stung. Performance times are April 29, 30, and May 1 at 7:30pm, May 2 at 8pm, May 3 at 1pm and 8pm, and May at 1pm and 6:30pm. 

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  • Things to do

For the past 40 years, this annual spring celebration has celebrated emerging artists from a wide variety of crowd-pleasing genres. This year, they take on the ‘70s with modern twists on classic rock, the timeless hits of Fleetwood Mac, and tunes highlighting the ever popular yacht rock. The legendary venue Passim will also showcase artists from the Folk Collective on the Rachael Solem Memorial Stage, and dance lovers are not to miss more than 30 troupes on the Deborah Mason Dance Stage. The 3rd Annual Asian Street Food and Music Festival will also share the neighborhood, with an Asian cultural fashion show, performers, live bands, and dancers.

  • Things to do
  • West End

Part telephone hotline, part vinyl record, and part live performance, Utopian Hotline uses real voicemails left on a public hotline to create a moment of community — inviting audience members to re-imagine our shared future. A cosmic conversation with Theater Mitu’s latest creation and inspired by the 1977 NASA Voyager mission (the launch of a vinyl-style recording of sounds found on Earth into space), as well as Covid-19 pandemic uncertainty and isolation, this experimental performance asks: what would our next message into the distant future be? This collaborative performance from May 1-18 is done in partnership with SETI Institute, Arizona State University’s Interplanetary Initiative, and Brooklyn Independent Middle School.

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  • Health and beauty

Go on an unforgettable adventure with your BFF when you board the Bestie Bus for a luxury round-trip to Canyon Ranch in Lenox, in collaboration with Yankee magazine. Departing Boston on May 1 at 1:30pm and returning May 4 at 12:30pm (but you can make your reservations now here), the journey from Boston to the Berkshires comes complete with onboard spa treatments, bubbly, and special road-trip playlists – plus, a few surprises along the way. Once on property, you’ll both enjoy a special double occupancy room rate, four spa treatments each, 30-plus daily activities, and much more. The event’s schedule includes group dinners, a tequila tasting, sound baths, a Kentucky Derby hat decorating and watch party, campfire with s'mores, and more. And of course, you'll enjoy unlimited meals and snacks, as well as use of the facilities, classes, two pools, property hikes, and more.

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