Labor Day Weekend Events in Boston

Photo © Kate Wood/World Ocean School

There aren’t many other phrases that can make a Bostonian cringe more than “Labor Day Weekend.” After all, this is annually the most difficult stretch of days for getting around within city limits. U-Hauls, vans, and other moving trucks will clog the streets, as thousands of college students return to Boston for the school year in what is popularly known as the “Student Invasion.”

Try to navigate certain sections of Allston, Brighton, Newton, or Kenmore Square on these days, and you’re liable to be stuck in traffic for some time. The solution? Take public transportation and check out some these area Labor Day weekend events.

Gloucester Schooner Festival
The annual schooner festival takes place in America's oldest seaport. Close to 50 ships are expected to participate in two days of racing, celebration and events, including Sunday’s “Mayor’s Race.”

Deutsche Bank Championship
This annual stop on the PGA Tour takes place in Norton, home of the TPC Boston. Click here for ticket information. Since its inception, the tournament has raised more than $20 million for both the Tiger Woods Foundation and local, New England-based charities. The Norton course is considered one of the top golf destinations in the entire region. 

Boston Tattoo Convention
The annual festival takes place at the Boston Sheraton with a myriad of events, including a beer garden, tattoo of the day, illusionist performance, and black cat burlesque performance. Tickets are $20 per day, or a four-day weekend pass can be purchased for $45, as well as a few VIP options. Purchase here.

Berklee Jazz on Spectacle
Head to Spectacle Island and catch the soothing sounds of Berklee School of Music’s Lihi Haruvi. The concert is free, however the ferry to the island is not. ark ferries depart frequently from Long Wharf, Boston to Spectacle Island. Boston Harbor Islands suggest arriving 30 minutes to departure. Fares are $15 for adults, $9 children ages 3-11.

Transgressors and Transformers, 1919-6904
Boston by Foot presents this annual five-hour walking tour so that guests may receive a unique and in-depth look at Boston during the time period of 1919-69 and how it has evolved into the city we know today, Tickets are $20, $5 for Boston by Foot members.

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