4.3 min readBy Published On: May 4th, 2023Categories: See and Do0 Comments on Weekend Picks – May 5th

Celebrate Cinco de Mayo

Celebrate Cinco de Mayo by drinking margaritas and chowing down on chips and guacamole. Cinco de Mayo (for those of you who flunked high school Spanish) is on May 5th.  Here are some local neighborhood businesses that are celebrating! 

Karaoke at Fat Baby

On Fridays, we sing at Fat Baby!  Karaoke starts at 9:30pm.

Kentucky Derby

And they’re off!  It’s the 149th running of the Kentucky Derby at Churchill Downs.  20 horses will compete, and only one lucky winner will receive a $2 million purse!  The most exciting two minutes in sports begins at 6:40pm on Saturday, May 6th!  Here’s where to drink Mint Juleps, where fancy hats, and watch the race! 

Seaport Sweat is Back

Seaport Sweat is one of Boston’s largest free outdoor exercise programs, offering over 100 classes from May to September. Located on Seaport Commons, all levels of fitness are welcome. There are a variety of classes, including pilates, yoga, HIIT, and Zumba. The classes are offered starting at 5:30pm Monday through Thursday and 10 am on Saturdays.  You can learn more here!  Here are some more suggestions for free fitness in the neighborhood!

The Return of the Lawn on D

The Lawn On D is back for Season 10, featuring a whole summer of fun, including live music, food, drinks, family-friendly events, and pickleball!  The Lawn On D’s most iconic feature, the Swings, will be back too!  Lawn on D will be kicking off the season with a Cinco De Mayo Party!  You can get the details here! 

The Greenway Food Truck Festival

The Greenway Food Truck Festival is happening on the same day as the opening day of the Greenway Artisan Market from 11a-3p on Saturday, May 6. It will feature 10+ food vendors serving up everything from cookies to kimchi fried rice.

New Spring Arrivals at The Point Clothing Lounge

Refresh your wardrobe, gentlemen! The Point Clothing Lounge announced on Instagram their new spring line!  You can shop spring arrivals in-store or by visiting here! 

We Jammin’! One Love. One Price.

PKL is now hosting a Reggae Bottomless Brunch on Sundays 11-3 featuring live reggae music! Cost is $25 – you can check out the menu here via Instagram! 

SoWa Returns for a New Season

The SoWa Open Market is one of the largest open-air farmer and artist markets in Boston. With a variety of regional and local vendors, plus food + beverage trucks, nestled among artist studios, galleries, and retail shops on the pedestrian-only Thayer Street, the SoWa (South of Washington) community becomes a vibrant gathering place every Sunday, May – October. Get more details here. 

Free Blue Bikes on Sundays in May

 In recognition of Mental Health Awareness Month and National Bike Month, Blue Cross Blue Shield of Massachusetts is sponsoring free Bluebikes Adventure Passes every Sunday in May, beginning on May 7, as part of their second annual “Miles for Mental Health” initiative. The free Adventure Passes will be available across the Bluebikes system’s 13 municipalities (Arlington, Boston, Brookline, Cambridge, Chelsea, Everett, Malden, Medford, Newton, Revere, Salem, Somerville, and Watertown). For this activation, riders can take advantage of free unlimited, two-hour Adventure Passes each Sunday in May by downloading and opening the Bluebikes App on a mobile device and selecting “Adventure Pass.”

Barre at the Beer Hall

Harpoon Brewery will host a free exercise class on Saturday, May 7th at 11am with a free class from Pure Barre. Pure Barre is leading a 50-minute classes that focus on low-impact, high-intensity movements. You can register here. Make sure to bring a yoga mat, water, and sneakers. Register here! 

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!

Live Music Roundup

DJ Kait will be playing for the last time at Shenannigans on Friday at 10pm.  Get your dancing shoes ready!

Lincoln features Legend of Summer Band on Sunday at 6pm.

Roza Lyons will have Jules + Gerry on Sunday from 7pm-10pm.

Loco is featuring DJ Tommy D on Friday from 1pm-4:30pm in the Lounge followed by DJ An Sounds from 5pm-8:30pm and DJ Colin Tonge from 9pm-close.  On Saturday, it’s DJ Colin Tonge from 9pm-close.  On Sunday, Zane Christopher in the main space from 2pm-5pm.


The Celtics will play the 76ers in Round 2 of the NBA Playoffs on Friday at 7:30pm and Sunday at 3:30pm.  The Red Sox face the Phillies this weekend with games on Friday at 7:05pm, Saturday, 7:15pm, and Sunday at 1:35pm. Here are 10 Places to Watch in the Neighborhood! 

Open Houses

161 Tudor Street, Unit 1 – Saturday 1-2:30pm and Sunday 11am-12pm.

9 Glover Court – Saturday 11:30-12:30

Check back, as this list may be updated over the weekend. 



Leave A Comment