Explore Boston

Boston Family Fun For Labor Day Weekend

Five fun activities to celebrate the last long weekend of the summer.

Boston honors Labor Day by providing plenty of venues for residents and visitors. Many are annual programs that people keep coming back for every year. Others are first-time occurrences that visitors look forward to seeing. Whatever they are, it is a time when people all come together to celebrate another significant holiday weekend. 

Five Events in Boston During Labor Day Weekend

Red Sox Game

On Thursday before and during the Labor Day Weekend, September 1 to September 4, the Red Sox will once again be playing at Fenway Park. Bring your family and enjoy the games between the Hometown boys and the Texas Rangers. 

Fenway Park Boston | WHERE Traveler®
Fenway Park (©Lauren Thimmesch)

2022 King Richard’s Faire, the New England Renaissance Festival

In its 41st season, King Richard’s Faire, the New England Renaissance Festival takes place in a Renaissance village setting with entertainment such as acrobats, fire eaters, jugglers, comedy acts, fabulous food and more spread over an 80-acre wooded site. Visitors will enjoy the performance of talented and skilled entertainers all through the day. The event takes place every weekend from September 3 to October 23, 2022. It also includes Labor Day, September 5 and Columbus Day, October 10. 

Renaissance Festival | WHERE Traveler®
Renaissance Festival (©Gio Bartlett)

Brookfield Orchards

Brookfield Orchards is open for apple picking starting Labor Day Weekend. Wagon rides are available from 1:00 p.m. to 4:00 p.m. in the afternoon on Labor Day. There will also be live music from Wibble on Monday, September 5, from noon to 4:00 p.m. 

Apple Picking | WHERE Traveler®
Apple Picking (©Terra Slaybaugh)

Gloucester Schooner Festival

The Gloucester Schooner Festival takes place over the Labor Day Weekend from September 1 to 5 this summer. More than 20 schooners will be welcomed back to celebrate the annual festival. All sizes and conditioned schooners will visit Gloucester Harbor throughout the weekend. Visitors get to watch the special parade called Parade of Sail on Sunday morning. It is a spectacular sight that one shouldn’t miss. For more updated information, check online for everything you need to know about this special event. 

Sailing | WHERE Traveler®
Sailing (©Ian Keefe)

Marlborough Labor Day Parade

The Marlborough Labor Day Parade is one of the largest parades in New England and is only a short drive away from Boston. It is a fun-filled family event, and it’s recommended to get there early in order to obtain a good spot to watch the festivities starting at noon on Labor Day, September 5.