Things to do in Boston this weekend of May 19 | 2023 AAPI 5K

Things to do in Boston this weekend of May 19 | Image credit: Boston Road Runners

Our picks for fun things to do in Boston this weekend of May 19 – 21 include 2023 AAPI 5KPolish Fest Boston2023 New England VegFest, 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 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 Memorial Day 2023 Sales in Boston, Thrift Stores in Boston, Boston Hiking and Biking Paths, Golf Courses Near Boston, and Instagrammable Places in Boston!

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 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 May 19, 2023 – Friday

Boston Harbor Sunset Cruise

Enjoy a romantic date with your partner or some bonding time with the family this Friday with a wonderful Boston Harbor Sunset Cruise. 

The meeting place will be at Bay Point Marina in Quincy. And from there, you’ll head out of Town River and into the waters of Boston Harbor. There, you can take in the beautiful views of the Boston skyline and enjoy the splendid colors of the sunset. 

The average trip is three hours which gives just enough time for sightseeing and basking in the sunset beauty.

When: Friday, May 19, 2023, 5 p.m. – 8 p.m.
Where: Bay Point Marina, 64 Washington Ct, Quincy, MA 02169
How Much: $110

Get The Lowest Price On The Very Popular Boston Hop On Hop Off Trolley Tour

Free Museums in 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, May 20, 2023

Esplanade 5k

Esplanade 5k

Image credit: Charles River Esplanade

Run the most popular route in Greater Boston with friends or family this weekend at the 2023 Esplanade 5k! 

The course will take you through an unparalleled riverfront route where you can enjoy both garden and water views set against the beautiful Boston and Cambridge skylines. And at the finish line, you can take your victory photo with a backdrop of passing sailboats on the Charles River. 

Please take note, online registration closes on Friday, May 19th. But you can still register on the day of the event at the venue.

When: Saturday, May 20, 2023, 9 a.m. – 12 p.m.
Where: Hatch Memorial Shell, 47 David G Mugar Way, Boston, MA 02108
How Much: $35 – $55

2023 AAPI 5K

Things to do in Boston this weekend of May 19 | 2023 AAPI 5K

Image credit: Boston Road Runners

Celebrate Asian American and Pacific Islander Heritage Month with a heart-pumping run this weekend! The run will highlight the vibrant Asian American community and organizations that work all year round to create safe and welcoming spaces for everyone. Proceeds from the run will go to local AAPI non-profits.

When: Saturday, May 20, 2023, 9 a.m. – 12 p.m.
Where: Carson Beach, 2010 William J Day Blvd, Boston, MA 02127
How Much: Not indicated

Fenway Card Show at Fenway Park

Calling all sports fans out there! The two-day multi-sport collectible and memorabilia show is returning to Fenway Park! 

Get to browse items from over 100 collectors, dealers, exhibitors, licensors, hobby heavyweights, manufacturers, and industry innovators from all over the world. From new and vintage sports card products to autographs, memorabilia, and groundbreaking physical and digital collections, you’ll find everything here. 

When: Saturday – Sunday, May 20 – 21, 2023, 9 a.m. – 5 p.m.
Where: Fenway Park, 4 Jersey St, Boston, MA 02215
How Much: $20

2nd Annual Canton Heritage Festival

Have an uber fun weekend with your friends or family at the 2nd Annual Canton Heritage Festival. And get ready because there’ll be so many things to check out. 

There will be live performances all day long, food trucks and food booths with all sorts of different cuisines, and fun activities like inflatable obstacle courses, live animals, face painting, games, and many many more. 

There will also be a food drive. You can bring non-perishable items here which will go to the Canton Food Pantry.

When: Saturday, May 20, 2023, 10 a.m. – 3 p.m.
Where: Paul Revere Heritage Site, 4 Rolling Mill Way, Canton, MA 02021
How Much: Free

Boston Open Market

Boston Open Market

Image credit: New England Open Markets

Enjoy the fresh air of the outdoors while doing some shopping this weekend at the Boston Open Market! Browse through the goods of over 60 local artists from one-of-a-kind original artwork and handmade jewelry to small-batch soaps and vintage leather coats. There is something for everyone here so keep your eyes peeled.

When: Saturday, May 20, 2023, 11 a.m. – 6 p.m.
Where: Boylston Street, 215 Boylston St, Boston, MA 02130
How Much: Free

LadiesCon 2023

LadiesCon is here! Celebrate everything comics, sci-fi, cosplay, fantasy, and many other realms of pop culture with a special focus on women, non-binary people, and the LGBTQ+ community. Keep your eyes out for panels, shopping opportunities, and special guests.

When: Saturday, May 20, 2023, 11 a.m. – 5 p.m.
Where: The Armory, 191 Highland Ave #1c, Somerville, MA 02143
How Much: Free

Franklin Park Kite and Bike Festival

Franklin Park Kite and Bike Festival

Image credit: Gina Toney

Head out to Franklin Park this weekend and join this 50-year-old spring tradition with your family. 

For kite flying, you can bring your own handmade kites, buy one, or make a kite onsite with Kite Team Haiti. There will also be a bicycle repair station, bikes to try for younger kids, free helmets, and food trucks to enjoy.

When: Saturday, May 20, 2023, 12 p.m. – 4 p.m.
Where: Franklin Park Playstead, Pierpont Rd, Boston, MA 02119
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!!!

Things to do in Boston this Weekend of May 19, 2023 – Sunday

Polish Fest Boston

Polish Fest Boston

Image credit: Polish Fest Boston

Celebrate the rich culture, traditions, and contributions of the Polish-American community in Boston with a day of food, lively music, cultural experiences, and the warmth and hospitality of the Polish-American community. 

This year, the event will raise funds for the Polish American Heritage and Community Foundation for its mission to support the community and raise money for cultural and community initiatives projects, events, and scholarships.

When: Sunday, May 21, 2023, 12 p.m. – 6 p.m.
Where: Polish American Citizens Club, 82 Boston St, Boston, MA 02125
How Much: Free

Elderbration & Walk To End Elder Isolation

Support the elders in the community and help end elder isolation with this walk!

The walk will start and end at Rogerson House. It will first begin with a program then after the walk, there will be snacks, ice cream, a photo booth, dancing, prizes, multicultural music, and so much more. You can also bring your furry friends for the walk.

When: Sunday, May 21, 2023, 9 a.m. – 12:30 p.m.
Where: Rogerson House, 434 Jamaicaway, Boston, MA 02130
How Much: Free

2023 New England VegFest

2023 New England VegFest

Image credit: New England Veg Fest

Whether you’re a vegan or not, you’re invited to celebrate vegetarianism at the New England VegFest. Get to sample and buy delicious vegan food and other plant-based products. You can also learn more about vegetarianism from acclaimed speakers and a variety of free workshops. 

When: Sunday, May 21, 2023, 12 p.m. – 5 p.m.
Where: Worcester State University – Wellness Center, 486 Chandler St, Worcester, MA 01602
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.

Latest posts by Liezel L. (see all)