- savor + roam
- Posts
- What to do in Boston this weekend (May 16 - 18)
What to do in Boston this weekend (May 16 - 18)
mother's day markets + rooftop yoga
Nicole Tommasulo
15 May • Estimated Reading Time: 20 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.
Like the newsletter? Feel free to buy me a coffee.
food news
Caffe dello Sport has officially opened its second location in East Boston (973 Saratoga Street, East Boston, MA 02128), across the street from the MBTA Orient Heights station. The cafe has been a North End staple for over 30 years, serving espresso, panini, gelato, cannoli, and cocktails. The new cafe has a similar menu and standing espresso bar for those who need a quick caffeine fix.
ICYMI, Michelin Guide is coming to Boston as part of its new Northeast Cities category. In addition to its preexisting guides in Washington, D.C., Chicago, and New York City, the Guide will include Boston and Philadelphia. Boston’s Guide will include Cambridge, Somerville, “and beyond” to showcase gastronomical gems “in the close surrounding areas if something exceptional is uncovered.” (Easter Boston)
travel news
Whether you’re already planning a trip or you’re looking for inspiration, I wrote up my rundown of the best places to eat, sleep, drink, and go to the beach on Nantucket. (savor + roam)
Airbnb is evolving with the launch of its new Services feature and overhaul of its Experiences section. Under Services, you can book salon appointments, spa treatments, yoga classes, and even chefs or catering services. They announced Airbnb Originals, which offers users one-of-a-kind experiences exclusive to their platform. (Conde Nast Traveler)
Fact-based news without bias awaits. Make 1440 your choice today.
Overwhelmed by biased news? Cut through the clutter and get straight facts with your daily 1440 digest. From politics to sports, join millions who start their day informed.
unique things to do in Boston:
may 16 - may 18
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.
It’s opening weekend for Boston Harbor Islands, and to celebrate, there will be Free Ferry Weekend, with rides between Long Wharf North and Spectacle Island. Ferries depart from Boston at 10:30 am and 12:30 pm, with return trips scheduled for 1:30 and 3:30 pm. Free rides are happening on Saturday, May 17, and Sunday, May 18, on a first-come, first-served basis at the Boston Harbor City Cruises Ferry Center at Long Wharf North.
friday
may 16
festivals + parties
Boston is celebrating National Bike to Work Day on Friday, May 16, with neighborhood group rides and a festival in Boston City Hall Plaza (1 City Hall Square, Boston, MA). Stop by between 7 and 9 am for a pastry and coffee before work.
The USS Constitution will be Underway from Charlestown Navy Yard beginning on Friday, May 16, at 10 am. The cruise will be visible from the Boston Harborwalk, Castle Island, and Charlestown Navy Yard. A 21-gun salute is scheduled for 11:30 am and will be viewable from Fort Independence on Castle Island.
Summer is almost here, and Short Path Distillery (71 Kelvin St, Everett, MA, 02149) is celebrating with Old Fashioned Night on Friday, May 16. Leave it to the pros with a Signature Old Fashioned, or build your own, choosing between a variety of spirits, house-made syrups, and bitters. Short Path will also be serving up Old Fashioned Flights and will have Reunion BBQ on hand with mouthwatering bites to pair with your whiskey. No ticket or RSVP is required.
classes
Start your weekend with a Sip & Dip class with Union Square Donuts at Boston Public Market (100 Hanover St, Boston, MA 02108) on Friday, May 16, from 5:45 to 7 pm. Tickets are $50 and include one complimentary beer or glass of wine, a box of six assorted brioche doughnuts, assorted homemade glazes for dipping, and toppings to decorate your doughnuts.
wellness
Begin the weekend by learning The Skill of Chill with Eoin Finn at Down Under School of Yoga Brookline (1054 Beacon St, Brookline, MA 02446) and via live stream. Here, you’ll gain insights into the link between breathing physiology and emotional regulation, plus the Blissology 3D Breath technique from Eoin’s book, Yoga Optimized. After a lecture, you’ll move through a slow-flow yoga. Tickets: $45.
saturday
may 17
festivals
The Boston Public Library’s Roxbury Branch (149 Dudely St, Roxbury, MA 02119) is holding its third annual Greater Roxbury Book Fair on Saturday, May 17, from 9 am - 5 pm. There is a full program of author talks, panels, workshops, storytimes, BIPOC vendors, food, music, and more.
Grab your lawn chairs and picnic blankets and head to the Greenway Spring Fest at Rowes Wharf Plaza (Atlantic Ave/High St, Boston, MA 02110) on Saturday, May 17, from 11 am to 5 pm. Come out and enjoy more than 15 food trucks, free fitness classes, face painting, a DJ, shopping at the Artisan Market, and local brews at Trillium Beer Garden.
markets
Shop over 20 local women-owned businesses at the Boston Women’s Market at Downtown Crossing (10 Summer St, Boston, MA 02110) on Saturday, May 17, from 11 am to 4 pm. Vendors will showcase their current favorite products, whether new launches or seasonal staples.
Afterward, head to Harvard Square for a massive Block Party & Vintage Market, where you can shop over 100 vintage, Y2K, jewelry, and other local vendors. The market will be open on Saturday, May 17, from 12 - 7 pm.
Or, head to Rococo Floral Co. (231 Somerville Ave, Somerville, MA 02143) for their Spring Vintage Market on Saturday, May 17, from 11 am to 5 pm. Shop florals, vintage home goods, and apparel while enjoying backyard picnic vibes.
wellness
Start your Saturday with Outdoor Morning Yoga at Remnant Brewing (2 Bow Mkt Way, Somerville, MA 02143) on Saturday, May 17, from 9 - 10 am. Tickets are $15. Please bring your own mat, sunscreen, and water. If there’s rain, the class will be held indoors.
Blend science with the art of stretching at the Stretch into Happiness: Blissology Movement Principles class with Eorin Finn on Saturday, May 17, from 1:30 - 4 pm at Down Under School of Yoga Back Bay (1112 Boylston St, Boston, MA 02215) and via live stream. Drawing from Eoin’s book, Yoga Optimized, “you’ll learn how to engage muscles to create precise, effective stretches that dramatically enhance flexibility while keeping your joints safe and happy.” Tickets are $55.
sunday
may 18
markets
Shop over 30 women-founded small businesses at the Boston Women’s Market at Assembly Row (375 Artisan Way, Somerville, MA 02145) on Sunday, May 18, from 11 am to 4 pm.
classes
Learn how to make different types of dumplings and Cantonese small plates at the Dumplings + Dim Sum Class at PAGU (310 Mass Ave, Cambridge, MA 02139). During the class, you’ll learn various ways to fold dumplings while enjoying popular dim sum dishes. Tickets are $119.
wellness
Learn the concept of DUO — Dynamic Unifying Opposition — to create grounded yet spacious yoga postures at the Yoga Optimized: Melt My Shoulders, Bliss My Hips class with Eoin Finn on Sunday, May 18, at Down Under Yoga Porter Square (2000 Mass Ave, Cambridge MA 02140) or via livestream. You’ll explore techniques like “myofascial tuning” and “Sensation-Guided Attunement” to help refine your yoga poses “and release years of stress and tightness.” Tickets: $55.
Small Budget, Big Impact: Outsmart Your Larger Competitors
Being outspent doesn't mean being outmarketed. Our latest resource showcases 15 small businesses that leveraged creativity instead of cash to achieve remarkable marketing wins against much larger competitors.
Proven techniques for standing out in crowded markets without massive budgets
Tactical approaches that turn resource constraints into competitive advantages
Real-world examples of small teams creating outsized market impact
Ready to level the playing field? Download now to discover the exact frameworks these brands used to compete and win.
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.
Like the newsletter? Feel free to buy me a coffee.
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
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.
Surround yourself with skyline views during a Saturday Community Yoga session at Rooftop@Revere, on top of Revere Hotel Boston Common (200 Stuart St, Boston, MA 02116), every Saturday from 10 - 11 am. Tickets are $10 and include a post-session smoothie.
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.
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.
pick-your-own farms
Celebrate the last days of tulip season with Pick-Your-Own-Tulips at Ward’s Berry Farm (614 Main Street, Sharon, MA 02067). Tickets are $20 and include a hayride to and from the tulip field, plus 10 stems. Ward’s is open daily.
artisan + farmers markets
Shop local artisans every Thursday and Friday 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.
The Boston Open Market returns to Boylston Street, between Arlington and Charles (across from the Boston Public Library), every Saturday through October from 12 to 5 pm.
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.
Jamaica Plain holds its weekly Farmers Market every Saturday from 12 pm to 3 pm year-round in the Bank of America parking lot (677 Centre St, Jamaica Plain, 02130).
The Unique Square Farmers Market returns for their 21st season in Somerville’s Union Square Plaza (66-70 Union Square Plaza, Somerville, MA 02143) every Saturday through October 25 (except Sept 20).
One of Boston’s largest open-air markets, SoWa Open Market (500 Harrison Ave, Boston, MA), is held every Sunday from 11 am - 5 pm until October 26. Stop by to shop various regional and local vendors, including food and beverage trucks.
Shop the Seaport Summer Market (88 Seaport Blvd, Boston, MA 02210) every Saturday and Sunday from 11 am to 7 pm. Like the winter market, the summer market is full of unique vendors selling everything from original artwork to pet goods. Food and beverages will also be available for purchase, and a DJ and game area will be available for all ages to enjoy.
Reply