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- What to do in Boston this weekend (May 2 - 4)
What to do in Boston this weekend (May 2 - 4)
happy market season to all who celebrate
Nicole Tommasulo
02 May • Estimated Reading Time: 21 minutes
Table of Contents
P.S. If you have an event, new attraction, new hotel, or restaurant opening you’d like me to cover, don’t hesitate to reach out.
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food news
Back Bay hotspot in deep water. Popular Italian restaurant Contessa has allegedly been shorting employees on their paychecks, according to a recent settlement agreement. While Major Food Group, the restaurant group that owns Contessa, denies any wrongdoing, employees claim they were shorted on tips over the last few years. (Eater Boston)
New eatery debuts in the North End. Earlier this week, My Mother’s Cutlets (371 Hanover St, Boston, MA 02113) opened its doors, specializing in hot sandwiches like the My Mother’s Special (cutlet, vodka sauce, and burrata) or The Hot Paisan, made with cutlet, prosciutto, mozzarella, hot honey, and basil. (Boston Restaurant Talk)
travel news
The REAL ID deadline is almost here. Beginning May 7, travelers planning on flying must have either a REAL ID or one of the legacy-approved forms of identification. (savor + roam)
ETIAS is being pushed back…. Again. The new European Travel Information and Authorization System (ETIAS), which would require travelers outside the European Union (EU) to apply and pay a fee before entry, is once again being pushed back. The new implementation timeline is in the last quarter of 2026, following the rollout of the new Entry/Exit digital border management system. (Afar)
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unique things to do in Boston:
may 2 - may 4
Everything here is happening this weekend only. Scroll down for recurring events every Friday, Saturday, and Sunday in Boston. Like the newsletter? Feel free to buy me a coffee.
all weekend
In honor of National Bike Month and National Mental Health Awareness Month, Blue Cross Blue Shield of Massachusetts is sponsoring a $50 credit for all Bluebike users during the month of May. The credit can be used for pedal and e-bike trips in 13 municipalities in Eastern Mass, including Arlington, Boston, Brookline, Cambridge, Chelsea, Everett, Malden, Medford, Newton, Revere, Salem, Somerville, and Watertown.
art shows
MFA Boston is holding its annual Art in Bloom celebration from Friday, May 2, through Sunday, May 4. Every year, floral design volunteers create arrangements inspired by different artworks in the MFA’s collection.
To celebrate First Friday, SoWa Art + Design District (450 Harrison Ave, Boston, MA, 02118) is hosting an Art Walk every day this weekend: Friday, May 2, from 5 - 9 pm, or Saturday, May 3, and Sunday, May 4, from 11 am - 5 pm. Many of SoWa’s artists will be on hand to talk about their work, much of which is available for purchase.
festivals + markets
Take a culinary journey across Asia at the Boston Panda Fest being held at City Hall (1 City Hall Square, Boston, MA) from 4 until 10 pm on Friday, May 2, from 10 am until 1 pm on Saturday, May 3, and from 10 am until 8 pm on Sunday, May 4. One of the largest outdoor food festivals in the country, there will be over 60 Asia food vendors with 200+ Asian street food options, plus vendors and cultural performances. Tickets range from $13 to $25.
The end of the Big Queer Food Festival is here, and to wrap things up, there will be a weekend-long Grand Tasting on Saturday, May 3, and Sunday, May 4, at High Street Place (100 High Street, Boston, MA 02110). Tickets ($100 - $250) include unlimited sips and snacks from dozens of restaurants, chefs, winemakers, and spirit brands from around the country. This includes Boston’s James Beard award-winning chef Karen Akunowicz (Bar Volpe), Potluck Desserts author Justin Burke of Columbia, South Carolina, and James Beard semi-finalist chef Arnold Mynt, who heads Nashville’s International Market.
Celebrate art and the artistic community of Cambridge this weekend at the Harvard Arts Fest, taking place from May 1 to May 4 on the Harvard University campus (52 Quincy St, Cambridge, MA 02138). The festival will showcase artwork in various mediums created by Harvard students, staff, and community affiliates, featuring a packed schedule of events.
Come out to Brighton for the first-ever multi-day Brighton Bazaar being held at Brighton Elks Lodge (326 Washington St, Brighton, MA 02135) on Saturday, May 3, and Sunday, May 4, from 11 am - 6 pm.
pick-your-own farms
Tulip season ends as soon as it begins, which means this is the final weekend for Pick-your-own Tulips at Wilson Farm (10 Pleasant, Lexington, MA 02421). Tickets are $19.99 and include ten tulip stems.
friday
may 2
wellness
Unwind from the week with a Relax, Renew, & Release Your Hips restorative yoga workshop on Friday, May 2, from 7:30 - 9 pm at Down Under School of Yoga - Brookline (1054 Beacon St, Brookline, MA 02446). Can’t make it in person? The class will also be live-streamed. Tickets are $30. Yoga mats will be available for rent for $3.
markets
New Recurring: Shop local artisans every Thursday and Friday beginning Thursday, May 1, and Friday, May 2, at the Downtown Boston Arts Market. Located in Downtown Crossing (8 Summer St, Boston, MA 02110) between Macy’s and Roche Brothers, this outdoor market will recur weekly from 11 am until 5 pm until October 24.
saturday
may 3
derby day
Spend the afternoon having sleek, stylish fun at the Derby on the Rooftop party at Rooftop@Revere at the Revere Hotel Boston Common (200 Stuart St, Boston, MA 02116) on Saturday, May 3, from 4 - 8 pm. Tickets are $50 and include two Woodford Reserve Mint Juleps, a curated selection of small bites, plus live coverage of the Kentucky Derby and a Hat Contest. The winner receives a free overnight stay at the Revere Hotel.
Dress to impress and come to the 3rd Annual Derby Day @ Tall Ship, Boston’s largest Derby Day party, on Saturday, May 3, from 3 - 7 pm at Tall Ship (1 East Pier Drive, East Boston, 02128). Prizes will be given out for the best hat and most dapper dressed, plus there will be a Maker’s Mark 360 Photo Booth, lawn games, Derby viewing, and more. Tickets begin at $20 and include a complimentary Maker’s Mark cocktail.
Dust off your derby hats and come to the Kentucky Derby Party at The Great American Beer Hall (142 Mystic Ave, Medford, 02155) on Saturday, May 3, from 4 - 6:30 pm. Miss Wednesday will be playing vintage jazz while the bar slings Derby-inspired cocktails and Southern-style bites. Admission is free. Food and beverages are available for purchase.
For Live DJs and themed cocktails, head to Derby Day at Time Out Market (401 Park Drive, Boston, MA 02215) on Saturday, May 3, from 4 - 8 pm. There will be prizes for best hats and good party vibes all day long. Entry is free, and food and beverages are available for purchase.
concerts
Immerse yourself in J.S. Bach: Mass in B Minor on Saturday, May 3, from 7:30 - 10 pm at Emmanuel Church (15 Newbury St, Boston, MA 02116). Tickets are pay-what-you-can for either in-person or live-stream viewing.
markets
New Recurring: Beginning Saturday, May 3, the Boston Open Market returns to Boylston Street, between Arlington and Charles (across from the Boston Public Library), from 12:00 to 5:00 p.m. If you miss this week, don’t worry; the market recurs every Saturday through October.
New Recurring: Alongside the Boston Waterfront, shop over 50 vendors at the Greenway Artisan Market on the Rose Kennedy Greenway. Beginning May 3, the market will be held every Saturday from 11:00 a.m. to 5:00 p.m. and every Saturday and Sunday beginning June 1.
festivals
Celebrate the Southwest Corridor Park (100 Boylston St, Boston, MA 02130) during the 47th Annual Wake Up the Earth Festival on Saturday, May 3, from 11 - 6 pm. Shop 120+ local vendors, artists, and restaurants, and enjoy live music in the beautiful park above the Orange Line Jamaica Plain and Roxbury fought together for.
Head to the North Shore this weekend for Wicked New England’s Halfway to Halloween Festival, being held on Saturday, May 3, from 11a to 7p at Salem’s Old Town Hall (32 Derby Square, Salem, MA). There is a full day of events planned, including Makeup Application Demos with Barrett’s Haunted Mansion and SpookyWorld, a DIY Upscale Halloween Decor workshop with Sketchy Panda Cult, and interviews with Witch City Walking Tours and Wicked Ghost Hunters. Tickets are $15.
tastings
Whether you’re sober, sober curious, or just cutting back on alcohol, don’t miss Founder Led Tasting with Tomorrow Cellars co-founder Tracey Sweeney at Dray Non-Alcoholic Bottle Shop (18 Union Park Street, Boston, MA 02118) on Saturday, May 3, from 2 - 4 pm. Come down for a complimentary tasting of the brand’s Rhône Blanc and Blanc de Rhône and learn about Tomorrow Cellars’ approach to non-alcoholic winemaking.
sunday
may 4
parties + festivals
Celebrate spring at the 40th annual Mayfair festival this Sunday, May 4 (rain date: May 1) from 11 am - 6 in Harvard Square (Two Battle Square, Cambridge, MA). This year, guests will be transported back to the 1970s, with musicians, dancers, and artists performing across multiple stages. Highlights include the Fleetwood Mac Tribute Band Little Lies, R&B artists The Presidential Suites, and Nashville’s Annie Scherer, who blends Lana Del Rey-style lyrics with Beatles-esque melodies.
Kick off the 5th a day early at the Cinco de Mayo party at Bow Market (1 Bow Mkt Way, Somerville, MA 02143), on Sunday, May 4, from 1 - 5 pm. This family-friendly event will feature a live DJ, face painting, plus food and beverage specials available for purchase. There will also be a Tequila & Mezcal Tasting Workshop for $50 a ticket. Otherwise, entry is free.
star wars day
Celebrate May the Fourth with a Star Wars Movie Marathon of the entire Star Wars saga at Lamplighter Brewing Co. - CX (110 North First Street, Cambridge, MA 02141) on Sunday, May 4, from 2 - 9 pm. Seating is first come, first served. Entry is free. Food and beverages will be available for purchase.
In honor of May the Fourth, Trident Booksellers & Cafe (338 Newbury St, Boston, MA 02115) is hosting the Book Wars: Sci-Fi & Fantasy Bookfair on Sunday, May 4, from 1 - 4 pm. There will be themed drinks available for purchase, tarot readings, star chart readings, droid building, and more.
Enjoy an evening of music from your favorite Star Wars films with the May the Fourth concert with the New England Film Orchestra at Somerville Theatre (55 Davis Square, Somerville, MA 02144) on Sunday, May 4, from 6 - 9 pm. Tickets range from $18 - $25.
markets
New recurring: One of Boston’s largest open-air markets, SoWa Open Market (500 Harrison Ave, Boston, MA), returns Sunday, May 4. The market will be held weekly from 11 am - 5 pm until October 26 and will feature various regional and local vendors, including food and beverage trucks.
wellness
Spend time relaxing and reconnecting with yourself before the start of a new week at a Sound Bath hosted by Blissful Monkey Yoga Studio (663 Centre St, Jamaica Plain, MA 02130) on Sunday, May 4, from 3 to 4 pm. Tickets are $30.
recurring spring events
As a reminder, the Commuter Rail has $10 weekend passes, which gives the ticketholder unlimited travel on Saturday and Sunday. The pass is activated during your first trip on Saturday and remains active until Sunday night.
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tours
Taste your way through Back Bay with a Back Bay Evening Chocolate Tour. For $55, take a guided walking + tasting tour of one of Boston’s most beautiful neighborhoods while learning Back Bay’s historical and architectural significance. Plus, enjoy tastings at four different locations where you’ll sample hot chocolate, cookies, cupcakes, and cake from Back Bay’s most iconic establishments.
The Boston Athenaeum routinely holds art and architecture tours throughout the week and on weekends. Tours are always free for members, $15 for adults, $10 for students, educators, and military personnel, $8 for children 11 and under, or $4 with your EBT, WIC, or ConnectorCare card.
Whether you’re a local or visiting Boston for the first time, there’s never a bad time to take a tour. For something a little different (and delicious), book a spot on the Freedom Trail: History Tour & Brewery Taste. Follow the Freedom Trail, stopping at 11 of 16 major landmarks along the trail, with Hub Town Tours before enjoying lunch and beer tasting at Democracy Brewing.
wellness
If you need a weekend pick-me-up, come to The Moxy Boston Downtown (240 Tremont St, Boston 02116) for Rooftop Yoga on Saturdays and Sundays from 9 - 10 am. Led by Julianne Maquire (Saturday) and Claire Metrick (Sunday) from YogaHub, you’ll flow through a dynamic vinyasa yoga experience, expending energizing movement with breath and community. Tickets are $25.
Start your weekend with a dose of wellness at The Hidden Art Gallery (25 Myrtle Street) in Beacon Hill, which hosts weekly Explore Meditation with Watercolor classes. Held every Friday from 3 pm - 6 pm, learn the basics of meditation while intuitively creating with watercolor. Classes are $55.
Reconnect with your ability to digest and rest during a Sound Bath Meditation with Ramon of Ib and Flow (247 Walnut St, Brookline, 02445). Sessions ($50) are held every Sunday.
Wind down from the weekend and prepare for the week ahead with a Grounding Meditation session every Sunday from 5 - 6 pm at Blissful Monkey Yoga Studio (663 Centre Street, Boston, 02130) in Jamaica Plain. Led by Licensed Mental Health Counselor Brennan Mallonnee, you will be guided through techniques on how to calm stress responses and practice trauma-informed grounding techniques for anxiety. Tickets are $20. Yoga mats, cushions, and blankets are available, but you can bring your own.
If you’re trying to bring balance into your life this year, start your Sunday brunch with a gentle yoga flow with Brewery Yoga at Lamplighter CX. The class is held every Sunday from 12:30 - 1:30 pm at Lamplighter Brewing Co.’s CX location (110 North First Street, Cambridge, 02141) in their upstairs taproom. Tickets are $25 and include a beer token or complimentary non-alcoholic drink.
classes + workshops
Whether you already love screenprinting or are completely new to this printing method, DARK MODE hosts DIY Screenprinting workshops at their storefront in Bow Market (1 Bow Market Way, #24) in Somerville on Friday (7 pm) and Saturday (6 pm and 7 pm) nights. Tickets are $45, including t-shirts.
DARK MODE also hosts Candle Making and Intention Setting Workshops every Thursday at 7 pm in their storefront at Bow Market in Somerville. Tickets are $50.
Spend your Friday learning to make classic Italian cuisine with Self Up Cooking Classes (19 Kingston St) in Downtown Crossing from 6 pm - 9 pm. Every week, they host an Italian Dinner with Tiramisu Finale cooking class and dinner experience, where you can learn how to make a three-course meal, including a luscious tiramisu for dessert. Tickets are $100 and include all ingredients.
tastings
Coffee lovers, this one is for you. Every Friday at 10 am, Counter Culture Coffee (374 Somerville Ave) in Somerville opens their Training Center for free coffee tastings. Anyone can learn and connect over perfectly brewed, high-quality, sustainable coffee.
Come to DeLuca’s Market Wine Cellar (11 Charles Street, Boston, MA 02114) in Beacon Hill for a free wine tasting every Friday from 4 - 7 pm. Every week, resident wine expert Donovan handpicks a mix of familiar favorites and bottles from up-and-coming vineyards or hard-to-find vintages to share among participants. No ticket is required.
Every Friday at 6:30 pm, GrandTen Distilling (383 Dorchester Ave) in South Boston holds Friday Night Flights: a chance to get to know their full line-up of spirits (plus special limited-run bottles not available elsewhere) at an intimate tasting. Tickets are $25, and seating is limited (10 max).
On Saturdays, Boston Harbor Distillery (12R Ericsson St, Boston, 02122) leads VIP tours ($50) and barrel-side tastings of their spirits ($20).
Love Child hosts free wine tastings every Friday from 5 pm to 7 pm and Saturday from 12 pm to 3 pm at their South Boston location (364 West Broadway). These tastings are free and require no reservations.
Come to The Urban Grape (303 Columbus Ave) in the South End on Saturday for The After Brunch, between 2 pm and 5 pm, for their weekly free wine tasting.
farmers markets
Farmer’s Market season never ends in Boston; it just moves inside. Visit Somerville’s Winter Farmers Market every Saturday from 9:30 am - 1:30 pm inside The Center for the Arts at the Armory (191 Highland Ave).
Jamaica Plain holds its weekly Farmers Market every Saturday from 12 pm - 3 pm year round in the Bank of America (677 Centre St, Jamaica Plain, 02130) parking lot.
Rosalind Village is celebrating the return of its Winter Farmers Market. Every Sunday from 11 am - 2 pm in the ABCD Parking Lot (32 Birch St, Boston, 02131), shop fresh produce, meat, fruits, and specialty foods, plus appearances from summer market favorites, including The Neighborhood Farm and Lilac Hedge Farm.
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