Weekend Picks – May 16th

Need weekend plans!?! Check out our weekend picks!
National Bike to Work Day is May 16th
Join a neighborhood-based group ride, or just show up for the fun. Going to work after the event is optional. 😉 Find more information about this year’s event on the City of Boston’s Bike to Work Day page. On Bike to Work Day, you can join a bike commuter neighborhood-based group ride from one of dozens of locations throughout the Boston metro area. Guided group rides with experienced ride leaders will follow a fixed schedule and route and finish together in Downtown Boston. Head to City Hall between 7 and 9 a.m. on Friday, May 16th. Enjoy some breakfast snacks and coffee. Stop by tents and tables to learn about local businesses and organizations that support our cycling community in the Boston region. The event is free, but registration helps the City to know you’re coming. Registration will close at 5 p.m. on Wednesday, May 14. You can still attend the event if you don’t register, but you will not be able to get a t-shirt during the event. Register here.
USS Constitution is Underway on Friday
USS Constitution is scheduled to get underway Friday, May 16, from Charlestown Navy Yard at 10:00 A.M. The cruise will be visible from the Boston Harborwalk, Castle Island, and Charlestown Navy Yard. A 21-gun salute will be fired at approximately 11:30 A.M., viewable from Fort Independence on Castle Island. Check her out!
Harpoon Summer Style Games at The Lawn on D
Ready for Summer? Stop by the Lawn on D on Saturday, May 17th, from 2 to 6pm for Summer Style Games on The Lawn. Harpoon and Life is Good are offering summer prize packs to participants. There will also be Harpoon’s latest brews to try. Don’t miss out! Get all the details here!
Sunday Sweat at Loco Lounge
Sunday Sweat is taking over The Loco Lounge for a group sculpt class on Sunday, May 18th at 10am. Studio78, CorePower, and Hot Box instructor Maryna Hoskins will be leading the 45 minute sculpt class, which is a great full body workout! The tickets are $25 and include the class, a mimosa, and complimentary patatas bravas! Get your tickets here! Don’t forget to bring your own mat!
Chaotic Singles Party at Capo Basement
The viral Chaotic Singles Party is happening at Capo Basement on Friday, May 16th from 6:30 to 9:30pm. You must be single, chaotic, and 21+ to attend. It is the perfect place to meet a love interest or friends! Ghost Tequila is sponsoring the event with free samples and light bites. Get all the details and tickets here!
Next Stop Comedy Stand Up Show
Castle Island Brewery will be hosting Next Stop Comedy on Friday, May 16th from 8 to 9:30pm. Next Stop Comedy showcases professional comedians from Boston, New York City and beyond! Each show features a novel line-up with acts seen on TV and heard on your favorite podcasts. Get your tickets here!
Bagel Brunch Open House in Savin Hill
The Carlisle Group is hosting a Bagel Brunch on Saturday featuring bagels, bubbles + city views at 13 Spring Garden Street, Unit 1 at 10am! You can learn more here!
New to the Neighborhood: Say Hello to Harry & Lou
There’s a new boutique landing on East Broadway just in time for summer—Harry & Lou is bringing effortlessly cool style and curated finds to the neighborhood, with pieces that make getting dressed feel fun again. From elevated everyday dresses and standout accessories to a few surprises for your pets, Harry & Lou is all about helping you find something for every occasion—whether it’s a birthday dinner, a work event, just grabbing drinks on the roof deck, or you need a gift. You can learn more here!
Seaport x Black Owned Bos. Market
Seaport x Black Owned Bos. Market is back with over 50 vendors. From gifts and apparel to packaged foods to beauty & skincare products. The market offers something for everyone. Come support your local black-owned businesses! Takes place on Sunday, May 18th from 12pm-6pm. You can learn more here!
Mass Fallen Heroes: Flags for The Fallen
Join Mass Fallen Heroes to support and honor those who have served and sacrificed for our country. They will be placing flags at 85 Northern Ave in The Seaport and are looking for volunteers to help. The flags will be a reminder for Patriot Week and Memorial Day. Get all the details to volunteer here!
Unity Farms Wellness Retreat with Summer Street Wellness
Looking to unplug, recharge, and maybe meet a rescue animal or two? Mark your calendar for Sunday, May 18th, and head to Unity Farm Sanctuary in Sherborn for a full-day Wellness Retreat that blends nature, mindfulness, and animal magic. Led by Krysta-Lyn and Jaclyn Marie Health, this retreat is all about finding peace, from the inside out. Think guided hikes through serene trails, journaling, sensory yoga among the animals, reiki meditation, and a sound healing savasana that might just lull you into a whole new level of calm. This event takes place on Sunday and you can get all the detail here!
Spring Fling in The Seaport
Get ready for Seaport Spring with a picnic for all ages on Saturday, May 17th from 12 to 3pm. There will be live music, complimentary bites, and beer to purchase from Castle Island Brewery. Dancers from Superette Salsa Nights, Seaport Sketch Artist, and Seaport Smalls will also be there! It is free to all and will be taking place at 111 Harbor Way.
Sake at Sunset at Nautilus Pier 4
What is better than a delicious dinner!?! A sake pairing to go along with it! Nautilus Pier 4 is hosting a sake and dinner pairing on Sunday, May 18th from 6 to 9pm. They will be offering a six course menu with a curated selection of spring sake. Get all the details and tickets 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!
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!
Celtics vs. Knicks on Friday at 8pm
Red Sox vs. Braves– Friday, May 16th at 7:10pm, Saturday, May 17th at 7:15pm, Sunday, May 18th at 1:35pm
Here are 12 Places to Watch the Game in South Boston!
Open House
138 West 8th Street – Saturday 11:30am-12:30pm
Check back as this list may be updated.
5th generation South Boston native, who rarely travels outside of Southie. Hobbies include grabbing drinks, walking around the neighborhood, and spending time with her bulldog, Chubbs. Her perfect day would be going on a stroll to get a coffee, followed by lunch at Loco, then drinks at Hunter’s, and grabbing a slice of pizza for the walk home.
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