Memorial Day Weekend is here!! Need weekend plans!?! Check out our weekend picks!

Backyard x Volo Softball Team

Join The Backyard Softball Team for the summer season! They are looking for 15 people to play. The games will be on Tuesday nights at Moakley. Cheering section encouraged!! Get all the details and sign up here!

Visit the Fallen Heroes Memorial in the Seaport

At the northern edge of Seaport Common, surrounded by the ever-changing light of the waterfront, stands a powerful tribute to those who made the ultimate sacrifice for a grateful nation. The first of its kind in the country, the memorial honors the Commonwealth’s brave servicemen and women who lost their lives fighting for our freedoms since September 11, 2001. Over 4000 flags have been planted to commemorate Memorial Day. The re-dedication for the Massachusetts Fallen Heroes Memorial is scheduled to take place on Friday, May 22, 2026 in the area of 85 Northern Avenue. The ceremony will take place from 10:00am. to 1:00pm. 

New Summer Cocktails at Local 149

Summer is here and so are refreshing cocktails at Local 149!! Some of our favorites include, Girl Dinner, cucumber vodka, lemon, simple, soda and Blue Collar Lemonade, Old Bardstown Bourbon, lemon juice, simple, crushed blueberries, soda water. Stop by this weekend and try them out! Make your reservations here!

Patio Season in Southie

Patio Season is here!  We will be enjoying the outdoors, even if the weather is a little chilly this weekend! Check out all the patios in the neighborhood and bring a sweatshirt! Drinks taste even better in the sunshine (even if it is just 60 degrees)! Check out our guide to get all the scoop!

Summer Menu at Lincoln

Lincoln just dropped their summer menu! They are featuring a Lobster Roll with a hot and cold option, as well as some new wraps, dishes, and desserts. We can’t wait to try the peach & blueberry cobbler! Make your reservation now!

Book a Beach Shack at Cisco Brewing Seaport

New for 2026, Cisco Brewers Seaport introduces 10 reservable Beach Shacks in the Cisco Beach area. Each private Shack fits 6–12 guests (up to 24 with adjoining units) and includes lounge seating, a cozy indoor nook with outlets + TV, stage views, and easy bar access. Guests also get skip-the-line entry. Reservations: $200 (2 hrs) or $250 (3 hrs), with drinks/food on a group tab + 20% gratuity. F & B not included in rental price. Book online up to 14 days in advance or on-site (if available). Groups reserving 2 or more Beach Shacks will be subject to private-event booking rates. Shacks are mostly outdoors, weather dependent, and held for 30 minutes past start time. No outside food or drinks allowed. Click HERE to reserve!

MDW Supplies at The Gallery

The Gallery at I and Broadway is your MDW headquarters fully stocked with plenty of beer, seltzers, wine and more!

Seaport Smalls

Seaport Smalls are taking over The Paseo at 111 Harbor Way, on Saturday, April 26th from 10-11am. It is a rotating free children’s program for ages 0-8. This Saturday will feature Curious Creatures – Live Animal Education. Refreshments will be available for purchase at Blue Bottle Coffee. Get more info here!

Rent a Fun Paddle Boat on Fort Point Channel

Pink Flamingo, Yellow Duck, Blue Swan, and Green Sea Monster can be seen along a dock behind the Boston Children’s Museum for the past few weeks. And many people had questions about rental availability. Well, the good people of the Children’s Museum found out that starting Memorial Day, these adorable boats are available for rent from the Charles River Boat Rentals.

Run to Remember

The Boston Run To Remember is back on Sunday, May 24th in the Seaport! This event offers both a Half Marathon and a 5 Mile course (available live or virtually) to honor our fallen first responders. It’s a great way to celebrate their service and give back to our community. Check out the registration details and more info here!

Live Music Round Up: 

The Playwright – features DJ sets on Fridays and Saturdays starting at 9pm followed by Country Sundays with live bands starting at 6pm.  Check out the schedule here!

Cisco Brewing Seaport – featuring live music throughout the week and weekend – follow on Instagram to see who’s playing

Hunter’s – Friday 5-8pm, Saturday 1-4pm, and Sunday 3-6pm and 9pm-12am.  Follow Hunter’s on Instagram for their schedule!

Capo – In addition to Sinatra Sunday with Rich Dimare and the Ron Poster Trio on Sundays at 5pm, there are live bands and DJ sets on Fridays and Saturdays.  Follow Capo on Instagram for the schedule!

Lincoln – DJ Sets starting at 10pm on Friday and Saturday. Rotating live bands on Sundays at 6pm.

Grace by Nia – features live music all weekend long!  You can check out the schedule here. 

Loco –performers and DJ in the main space and the lounge on the weekend! Look on their Instagram story for lineup!

Park City – has live music all weekend long.  Follow them on Instagram for the schedule.

Cisco Brewing Fenway – Check out the latest live music happening at Cisco Brewing Fenway here. 

SPORTS!

Red Sox vs. Twins – Friday, May 22nd at 7:15pm, Saturday, May 23rd at 4:15pm and Sunday, May 24th at 1:35pm.

NBA Playoffs – schedule here

NHL Playoffs – schedule here

Here are 12 Places to Watch the Game in South Boston!

For more MDW 2026 suggestions visit our Guide here!