Weekend Picks – MDW 2025

4 min readBy Published On: May 22nd, 2025Categories: See and Do0 Comments on Weekend Picks – MDW 2025

Need Memorial Day Weekend Plans?!? We got you covered!

Seaport Summer Market

The market will be open on Saturday and Sunday from 11am to 6pm. There will be artisans and local stores with clothing, jewelry, skin care, home decor, pet goods, artwork, food and more! There will also be an outdoor food and beverage area, a DJ, and games for people of all ages to enjoy. Get more info here!

Memorial Day Flag Garden

The City of Boston’s flag garden is on display through Monday at Boston Common. Each of the 37,000+ American flags planted at the Soldiers and Sailors Monument represents every brave Massachusetts service member who gave his or her life defending our country since the Revolutionary War.

Stretch and the City

Enjoy Free Yoga at the Summer Street Steps on Fridays at Noon from May  – September.  The official address is 400 Summer Street!  You can learn more here. 

Petula’s is celebrating its second birthday

For two years, Petula’s has been serving up craft cocktails and delicious food at the corner of L and 4th for one year! Stop by this week and wish them a Happy Birthday!  The patio is now open too!

Kick off the cookout season

Having a backyard cookout for Memorial Day weekend? Foodies can help you with when it comes to the meat you’re grilling!  From hot dogs to hamburgers to steak tips + delicious sides plus beer and wine, Foodies is one-stop shopping! 

Patio Season in Southie

Patio Season is here…well, if the weather cooperates! If we get lucky enough to see a sunny weekend day, check out all the patios in the neighborhood! Drinks taste even better in the sunshine! Check out our guide to get all the scoop!

The Handle Bar Memorial Day Sale

Get ready for summer with The Handle Bar! They are offering a fantastic Memorial Day Sale on class packs. 5 for $95, 10 for $180, and 20 for $340. It will be running from now till May 28th. Get all the details here!

Three Days of Playwright Brunch

Celebrate Memorial Day Weekend at The Playwright s for brunch! Because what is more American than day drinking at brunch! Brunch will be held Saturday, Sunday, and Monday from 10am to 3pm. They will also have brunch specials in addition to their  menu. Make your reservation here!  Plus don’t forget about Country Sundays!

Order a Case of Wine

Join Social Wines Social Club! The ‘Social Club’ is Social Wines affectionate name for their client list. When you check out at the register (name and email) they remember all of your purchases. It’s a great way to refresh your memory on wines you’ve tried and helps them make suggestions for other wines based on them. They also require Social Club membership for deliveries and can easily take phone orders by looking up your previous purchases. It’s free and helps Social Wines dial in those recommendations! So stop by pick up some wine and join the Social Club! Social wines is also offering a sale on a case of Le Poussin (aka pink chick). $104 gets you 12 bottles of 2022 Le Poussin Rosé, including delivery this Wed-Friday!

The Jackson Lunch at Fresh Boston

Fresh Boston is offering an awesome deal Tuesday through Friday from 11am to 5pm where you get a sandwich and draft beer or cold brew for $20. And yes, you read that right $20!! Make sure to stop by Friday to reap the benefits of the deal!

Thomas Fitzgerald Post is hosting its annual Memorial Day service on Sunday, May 25th:

0900 – Assembly at Post

0930 – Parade/March to Medal of Honor Park for the laying of the wreath ceremony at the SB Vietnam Veterans Memorial

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!

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 – Legends of Summer 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!

SPORTS!

Red Sox vs. Orioles– Friday, May 23rd at 7:10pm, Saturday, May 24th at 4:10pm, Sunday, May 25th at 1:35pm

Red Sox vs. Braves – Monday, May 26th at 2:10pm.

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

Check back as this list may be update!

 

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