Things to do in Boston this weekend of June 16 | Image credit: Powisset Farm
Our picks for fun things to do in Boston this weekend of June 16 – 18 include Father’s Day BBQ and Bluegrass, Boston Portugese Festival, Juneteenth Celebration at Muldoon Park, and more!
There’s always lots going on in Boston in terms of events and activities. There are fun things to do in Boston for adults and also Things to do in Boston with family. Our weekly round-up brings you the best things to do in Boston this weekend.
Editor’s Note: Our staff at localite.com makes every effort to bring you the latest updates on activities, entertainment, food, and drink specials in the Greater Boston area. However, all information is subject to change by the organizers. As always, please confirm before you make your plans!
For more on the latest in Boston, check out our Things to Do in Boston this Week and our Things to Do in Boston this Weekend with Family guides. These are also updated every week with the best on entertainment, food & drink, and deals across Greater Boston!
Also, check out our articles on Juneteenth Boston Events 2023, Father’s Day Events Boston, Father’s Day Deals 2023, and Boston Pride 2023!
Get the lowest price on must-see attractions in Boston with Boston CityPASS
Experience Boston’s must-see tourist attractions — and enjoy considerable savings — on this exciting Boston CityPASS. Visit the popular New England Aquarium and the Museum of Science. Plus choose 2 admissions between the following 3 attractions Boston Harbor Cruises, Harvard Museum of Natural History, or the Franklin Park Zoo to complete the experience.
This Boston CityPASS is valid for 9 consecutive days from the date of first use. Convenient mobile tickets are valid for 1 year from the date of purchase. Transportation to and from the attractions is not included. Attractions may be required to verify proof of COVID-19 vaccination before allowing entry. Please review attraction requirements before visiting Boston.
Get all the details and book your Boston CityPASS TODAY!!!
Things to do in Boston this weekend of June 16, 2023 – Friday
Donna Summer Disco Party 2023
Save the date! The Donna Summer Disco Party is back with a roller skating rink! The event honors five-time Grammy winner and Boston native Donna Summer. And it will feature O’Mega Red who’ll be performing the hit song “Angel” ft Donna Summer. There will also be appearances by members of Summer’s family including Mary Gaines Bernard, her sister who was her longtime backing vocalist.
When: Friday, June 16, 2023 | 6 pm – 9 pm
Where: Boston City Hall Plaza, 1 City Hall Square, Boston, MA 02203
How Much: FREE
Celebrate Juneteenth with Wee the People
For children ages 8-12, Kids notice a LOT, including skin color. They sense that it matters, and they have questions about how and why. Together we will explore how racism is not just one thing, but also a problem with many parts working together — problems that take more than individual kindness to solve
When: Friday, June 16, 2023 | 3:00 pm – 4:00 pm
Where: 690 Adams St, Dorchester, MA 02122
How Much: FREE
2nd Annual Boston Pun-Off
Get ready to laugh ’til your sides hurt this weekend at the 2nd Annual Boston Pun-Off! Contestants will go head to head with wordplay and race to get points from the judges and the audience. One by one, they’ll be eliminated until there’s one champion. The best parties that all rounds will be incorporating suggestions from the audience.
When: Friday, June 16, 2023 | 7:30 pm – 8:30 pm
Where: Rozzie Square Theater, 5 Basile St #2501, Roslindale, MA 02131
How Much: $16
Get The Lowest Price On The Very Popular Boston Hop On Hop Off Trolley Tour
Explore the best that Boston has to offer on this hop-on hop-off tour of the city. See Boston’s top attractions—like the USS ‘Constitution’ and the Boston Tea Party Ships and Museum, to name a few—on the loop. Enjoy discounted admission to attractions like the Boston Tea Party Ships and Museum with the purchase of your tour.
Board one of the orange-and-green trolleys at any of the stops and enjoy the view with live commentary from an expert guide who knows the city inside and out. Learn about the history and happenings of Boston, a city known as the Cradle of Liberty, as the trolley rolls along from one location to the next. For one, or two consecutive days, hop off at any of the attractions for a closer look, then hop back on when it’s convenient.
14 stops and 33 points of interest!
Get all the details and book your Boston Hop On Hop Off Trolley Tour TODAY!!!
Things to do in Boston on Saturday, June 17, 2023
Strawberry Festival at Cider Hill Farm
Image credit: Cider Hill Farm
It’s nice, huge, juicy strawberries everywhere at Cider Hill Farm! Enjoy live music, hard cider, family-friendly activities, and hayrides to celebrate the strawberry season. Of course, there will also be homemade strawberry treats and you can even pick your own strawberries.
When: Saturday, June 17, 2023 | 8:30 am – 4:30 pm
Where: Cider Hill Farm, 45 Fern Ave, Amesbury, MA 01913
How Much: Free
Juneteenth Jazz Celebration With the Fred Woodard Trio
Image Credit: fredwoodard.com
Celebrate Juneteenth with a jazz concert at the Mattapan Branch, featuring the Boston-based Fred Woodard Trio! This event will be held in the library’s back garden. Please bring a blanket or folding chair to sit on, grass can be damp! In case of inclement weather, the event will be moved indoors. This event is suitable for all ages.
When: Saturday, June 17, 2023 | 12:00 pm – 1:00 pm
Where: 1350 Blue Hill Ave,Mattapan MA 02126
How Much: FREE
The Big Bounce America Boston 2023: The World’s Biggest Bounce House
Image credit: The Big Bounce America
Get ready to get bouncy with excitement for the biggest, craziest touring inflatable event in the entire world! The world’s biggest bounce house is coming to Boston! Bounce over 13 000 square feet of climbing towers, ball pits, slides, inflatable obstacle courses, spaceships, sports fields, and many more! So drop the gadgets, step away from the TV, and get bouncing on this massive bounce party!
When: Saturday, June 17 – 25, 2023 | 9 am – 6 pm
Where: Topsfield Fairgrounds, 207 Boston St, Topsfield, MA 01983
How Much: Starts at $22
Night Shift Brewing Whirlpool 5k
Break a sweat with your pals this weekend with Night Shift Brewing’s 5k race! All ages and paces are welcome. After the race, you can enjoy the after-party at the brewery. You’ll also get a limited edition 2023 Whirlpool 5K commemorative shirt, one Whirlpool glassware, and two beer tickets
When: Saturday, June 17, 2023 | 9:30 am – 2:30 pm
Where: Night Shift Brewing, 87 Santilli Hwy, Everett, MA 02149
How Much: Not stated
Randolph Caribbean American Heritage Festival
Celebrate the rich and colorful Caribbean American heritage this weekend with the whole family! There will be amazing food, music, and, of course, a full-fledged celebration of the Caribbean American diaspora community in Randolph.
When: Saturday, June 17, 2023 | 11 am – 5 pm
Where: Powers Farm, 592 N Main St, Randolph, MA 02368
How Much: Free
Ashmont Block Party
Image credit: Greater Ashmont Main Street
Have so much fun this weekend with the whole family at the Ashmont Block Party! It’s going to be one whole block of fun including live story readings, a petting zoo, balloon animals, face painting, and so much more. As for the adults, there will be food trucks, art, live music, and a beer garden.
When: Saturday, June 17, 2023 | 1 pm – 5 pm
Where: All Saints parking lot, 209 Ashmont St, Boston, MA 02124
How Much: Free
Get the lowest price on the highly-rated Original Boston Guided Brewery Tour
Learn about Boston’s thriving craft beer scene and sample a variety of libations on this morning or evening brewery tour. Get an inside look at how beer is made and learn about their operations as you visit breweries, cider houses, and distilleries. Visit brewpubs that may include the well-known Samuel Adams or gastropub Meadhall. Round-trip transportation in downtown Boston by air-conditioned van is included.
Get to know Boston’s thriving beer scene on a morning or evening brew tour. Chat with brewery owners and learn about the equipment used to make beer, the brewing process and best of all, what the different kinds of beer taste like.
Get all the details and book your Original Boston Guided Brewery Tour TODAY!!!
Editor’s Note: It’s Father’s Day Sunday! Check out our articles on Father’s Day Events Boston, and Father’s Day Deals 2023 to see more ways to celebrate Dad on this special day!
Things to do in Boston this Weekend of June 16, 2023 – Sunday
Chelsea Carnival
Image credit: Fiesta Shows
Bring out the inner kid in you or have fun with the kids at the Chelsea Carnival! Get to ride unlimited rides during discount ride promotion days, enjoy the sights and sounds of the midway, and make memories with the whole family. There will also be tons of games and food to enjoy so enjoy it all before the carnival closes down for the season.
When: Sunday, June 18, 2023, 5:30 pm – 8 pm
Where: 295 Eastern Ave, Chelsea, MA 02150
How Much: Varies
Father’s Day BBQ and Bluegrass
Image credit: Powisset Farm
BBQ, beer, and bluegrass music – now that’s the perfect recipe to honor your dads on Father’s Day. Head on over with the whole family to Powisset Farm and enjoy authentic Blue Ribbon barbecue, lawn games, live bluegrass music, and visits with the barnyard animals. Beer and wine will be available for purchase.
When: Sunday, June 18, 2023, 12 pm – 2 pm
Where: Powisset Farm, 39 Powisset St, Dover, MA 02030
How Much: $30 for kids | $70 for adults
Juneteenth Celebration at Muldoon Park
Come celebrate Jubilee Day (aka Juneteenth) and Father’s Day! This event is outdoors (rain or shine), FREE of charge, and open to all, including your furry friends. There will be games, music, kayaking (weather dependent), Lowell National Historic Park: Art in the Park, Lowell Community Health Center Info Table, Small Business & Information Tables, gift bags (while supplies last), the LCCPS Afro-Percussion.
When: Sunday, June 18, 2023 | 12:00 pm – 5:00 pm
Where: Muldoon Park, 5 Billerica St, Lowell, MA 01852
How Much: FREE
Family Hike: Insect Safari
On Father’s Day, families need nature and learn about its beauty! The Arnold Arboretum uses nets and bug boxes to find insects in the meadow and the woods. Go on a StoryWalk® and look at insects with magnifiers!
Free and open to all, most suitable for children ages four through ten.
When: Sunday, June 18, 2023 | 11:00 am – 2:30 pm
Where: 125 Arborway, Boston, MA 02130
How Much: FREE
Coolidge Corner Theatre’s screening of “Dealing with Dad”
Father’s Day Events Boston | Image Credit: coolidge.org
Free to Coolidge members! Post-film Q&A with filmmaker Tom Huang, moderated by Boston Asian American Film Festival Director Susan Chinsen.
When: Sunday, June 18, 2023 | 2:00 pm
Where: 290 Harvard St, Brookline, MA 02446
How Much: FREE
Father’s Day Flapjacks + Flatbreads to benefit the Boys & Girls Club
Image Credit: rail trail flatbread co. FB Page
Help in giving back to the Boys and Girls Club of Metrowest-Hudson and help them by joining on June 18th for a special Father’s Day brunch! Bring your family and celebrate with flapjacks, flatbreads, or maybe even both!
When: Sunday, June 18, 2023 | 10:00 am – 2:00 pm
Where: Rail Trail Flatbread Co., 33 Main Street Hudson, MA 01749
How Much: Free – $40
2023 Boston Portugese Festival
Image credit: Boston Portuguese Festival
After four years, the Boston Portuguese Festival is back! Get ready to have so much fun and to dance to all the musical performances that will fill the day. There will also be so much food and many activities to do. Comedian Taylor Amarante will also be coming to steal the scene.
When: Sunday, June 18, 2023 | 12 pm – 8 pm
Where: City Hall Plaza, 1 City Hall Square, Boston, MA 02203
How Much: FREE
Stay on top of the latest events & activities in the Boston area with our weekly updates to Things to do in Boston this Week, Things to do in Boston this Weekend, and Things to do in Boston this Weekend with Family!
And to get these updates directly to your mailbox, you can follow us on Facebook by clicking the …next to the search icon lens.
