Weekend Picks – August 21st

Welcome to the Neighborhood, Pomona Cafe & Wine Bar
Pomona Café & Wine Bar is officially open in Maverick Square. Located at 18 Meridian Street, the new spot is part café, part wine bar, serving everything from Colombian coffee, breakfast and brunch to small plates, dinner, wine, and cocktails. The new Eastie spot is designed to be an all-day neighborhood gathering place — stop in for coffee in the morning, meet a friend for brunch, or settle in for wine and dinner later in the day. Welcome to the neighborhood, Pomona! We can’t wait to check it out.
Stop by The Blue Caboose
Check out the iconic blue train car on the Greenway for some delicious ice cream and coffee. Learn more on their Instagram.
Live Music at the Tall Ship
Head to The Tall Ship to see live music all weekend! Book a lounge!
Free Boating Safety & Learn to Kayak
Head to Constitution Beach for free kayaking and boating safety lessons, no cost, but you’ll need to email [email protected] and [email protected] to schedule your lesson. Friday, August 21st through Sunday, August 23rd, 10am-4:30pm, Constitution Beach, East Boston.
Treat yourself!
La Sultana Bakery features a variety of delicious baked goods, from cupcakes to flan; they even have Colombian specialties like palmertias and peras! You can check out the full menu here!
Early Voting Starts Saturday
Ready to cast your ballot? Early voting for the September 1 State Primary kicks off in Boston on Saturday, August 22, and runs through Friday, August 28. The deadline to register to vote is also Saturday, August 22. Get all the details of where to vote here.
The 2026 Boston Triathlon Weekend
The 2026 Boston Triathlon Weekend takes place on Saturday, August 22nd, and Sunday, August 23rd. Kids Day at the Boston Tri takes place on Saturday. The Boston Tri Olympic and sprint distance races will be held on Sunday morning and are open to all, followed by the professional spectator event! Get all the details here!
Live Mariachi at La Hacienda
Stop by La Hacienda’s beautiful patio on Friday night for live mariachi music, paired with delicious homestyle El Salvadoran and Mexican food. Open until 2am every day, it’s a great late-night hang whether you’re grabbing dinner or just stopping in for drinks. 150 Meridian St, Boston, MA 02128.
Boston’s Hidden Cocktail Experience
Step behind an unmarked door into Next Door, an intimate East Boston speakeasy. Get a welcome sip, pick two signature cocktails off the menu, and snack on a shared antipasto board while you learn the stories behind the drinks. 21+, 90 minutes, exact address revealed after booking. Book here.
Maker’s Market at The Grove
Spend your afternoon supporting local and shopping small! There will be a curated market featuring 25+ local makers and artisans on Saturday from 12 to 4pm. From unique jewelry and handmade goods to home décor, apparel, and specialty foods—there is something for everyone! It is the perfect way to enjoy a summer day in the Seaport, so come soak up the vibrant atmosphere at The Grove and meet some talented local creators! The Grove also launched a new menu featuring Mozzarella Sticks and Fried Coconut Shrimp! Get all the details here!
Sports Day on the Greenway
This Saturday (8/22) at the Bremen Street Park, it’s gonna be all sports, from 1- 4 PM! Check out this event for fun games and activities for all ages!
World Music Concert Series at Constitution Beach
Head to Constitution Beach on Saturday 8/22 from 3-4:15PM for a performance by Haitian Drummer Jean Eli Joseph!
Zumix Summer Concert Series: K^2
Wrap up the weekend at Piers Park (95 Marginal St.) Sunday from 6–8 PM for a free performance by K^2. Enjoy an evening of Mozambican and Ghanaian Fusion.
SPORTS!
Red Sox vs. Giants – Friday, August 21st at 7:10pm, Saturday, August 22nd at 7:15pm and Sunday, August 23rd at 3:15pm.
Patriots vs. Giants: Saturday, August 22nd at 7pm.
Here are 7 Places to Watch in the Neighborhood!
Check back as this list may be updated!
Have a fun weekend! Thank you to our Caught in Eastie readers and Neighborhood Partners for supporting our local journalism efforts!

Hi! I’m Carina! I’m a junior at Northeastern University doing my Co-op at Caught in Southie; I’m very excited to be here! My favorite Boston spots are Chez Vous Roller Rink and Show Malatang- you can find me there most weekends! I love hanging out with my friends, reading, pickles, hockey, roller blading, and anything to do with music. Reach me at [email protected] to talk Boston!


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Cool Off at a Splash Pad Dance Party in Eastie on Wednesday