4.8 min readBy Published On: August 25th, 2023Categories: See and Do0 Comments on Weekend Picks – August 25th

Citizens Pickleball Open at the Lawn on D

Lawn on D is hosting a first-of-its-kind charity pickleball tournament on Friday. The Citizens Pickleball Open (rain or shine) is a first-of-its-kind charity pickleball tournament in Boston. Major League Pickleball pros, local athletes, and influencers team up and face off in a “World Cup” style tournament! Throughout the evening, you can take free fitness classes on The Lawn, bid in the silent auction to benefit the Greater Boston Y, hang out at the mixer, and more.  The fun starts at 4 pm. Learn more here! The tourney continues on Saturday, followed by The Summer Send-Off Party from 12 – 4 p.m., sponsored by Viva that features live music, yard games, giveaways, and a free pickleball tournament.

Coffee for a Cause at Deja Brew

On Friday, pick up your coffee at Deja Brew and $1 of every cup sold will be donated to cancer warrior and Southie native Ursula Volosevich, who is battling breast cancer. 

Taylor Swift Harbor Cruise

Get ready for the voyage of your dreams as the Music City Queen sets sail into the Boston Harbor sunset. Dance to your favorite Taylor songs spun by the incredible DJ Joslyn Fox and enjoy live performances by Boston’s hottest Drag entertainment. Food. Drinks. Taylor. What more could you possibly ask for?! This three-hour cruise takes place on Friday at 9pm. You can learn more and get your tickets here!

Introducing The Shy Hour!

Enjoy 50-cent dunks, $3.50 beers, $9 sandwiches, and cocktails at Shy Bird. You get the idea!  Swing by any day of the week for snacks and drinks. It’s like happy hour, but it’s not, but kinda is. 🍻 Monday – Friday 4PM til 6PM AT SOUTH BOSTON  location! 🍔
Taste some Ice Cream at Fresh

Fresh is hosting an ice cream tasting with Jamie’s Ice Cream co on Sunday from 11am-1pm.

Faherty Dog Walking Club

Take your dog for a walk with Faherty in the Seaport – 70 Pier 4 Blvd on Friday at 10am.  Enjoy a light breakfast with your pup with treats brought to you by Blue Bottle Coffe and Polkadog Bakery!

Singles Mixer at Cisco Brewing in Seaport

Prevue Dating and Cisco Brewing are joining forces for a Singles Mix + Mingle on Friday from 3pm-5pm. You never know, right?

Seaport Sweat: LIT2LIFT

This 45 min hybrid workout consists of high energy, good music, and functional exercises to bring you a LIT experience! The workout starts with a warmup and ends with a cool-down.  You can register here for this FREE class! This class takes place on Saturday at 10am.

Shop Farmers Forge at Cannonball Cafe

Pick up some fresh fruits and veggies at Cannonball Cafe on Saturday from 9am-12pm.

Southie Saturday Run Club with MySTRYDE

Join MyStryde every Saturday at 8:30am from the South Boston studio for a 6-mile loop. Think you won’t have runners in your pace group? Think again! To make sure they support all levels and paces, they’re providing FIVE different pace groups (7/8 min per mile, 8/9 min per mile, 9/10 min per mile, 10/11 min per mile, and 11/12 min per mile) lead by our new run club pacers. Join the group this Saturday and enjoy a post run smoothie from @bamboobeachjuicebar on MySTRYDE!

Laugh Drag Brunch – Britney vs. Christina

On Sunday, enjoy a Drag Brunch at Laugh with a Britney vs. Christina Theme! The fun starts at 12pm.  Get the details here.

Celebrate National Dog Day at Little Words Project

On Sunday, bring your dog to Little Words Project in the Seaport for 10% off your purchase!  Plus enter a raffle for a basket full of goodies for your dog.  Raffle will benefit Sweet Paws Rescue.

Boston Beaded Pop-Up at Habit

Boston Beaded will be popping up at Habit on Sunday from 12pm-3pm.

Get some Fresh Seafood at The Boxes

On Sunday from 3-6 pm stop by The Boxes at Boston Fish Pier, Boston. This pop-up hosts a weekly seafood market featuring vendors from Fish Pier and rotating sessions by local nonprofits.

Live Music Roundup

DJ Stenny will be playing upstairs at Capo on Friday and Saturday night at 8pm. Downstairs at Capo it’s Steve Memmolo at 7pm.  Saturday, downstairs will be closed until 10pm for a private party.  On Sunday it’s the legendary Sinatra Sunday with Rich Dimare and the Ron Poster Trio.

Grace by Nia has The Mastadonis Project and Will and the Way on Friday. On Saturday, it’s The Mastadonis Project and Richie Rick + 24 Karat and on Sunday, it’s Cliff Weeks and The All-Star Band.

Lincoln has Legends of Summer Band on Sunday at 7pm.

Hunter’s has Ryan Flynn on Friday at 5pm.  On Saturday it’s Alex Brow at 3pm. On Sunday, it’s It’s Ya Boy KR at 2pm followed by Matty Sheehan at 9pm.

Parking + Traffic Advisory for Day Blvd. – Boston Triathlon

The Boston Triathlon is in town this weekend, and there will be parking and traffic restrictions!

There will be no parking on Day Blvd. from I Street To Shore Road and along Shore Road from Saturday, August 26th at 10pm – Sunday, August 27th at 2pm. On Sunday, August 27th – Day Blvd. will be closed from Kosciuszko Circle to Shore Road from approximately 5:30am-2pm. Read our feature on the Boston Triathlon – a 15 year retrospective – here! 

Check out our Summer Guide 

It’s summer in Southie – the hottest place to be! Forget Newport or the Cape. We’ve got it all right here – beaches, boats, roof decks, dining al fresco, and some of the coolest people around! We’ve got the scoop on everything that’s “Hot in Southie” this summer, from places to eat and drink apres beach, to summer workouts, outdoor music, and more. If it’s happening in Southie this summer, you’ll find it in our summer guide!

Check back, as this list may be updated. 

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