Labor Day Boston area

Boston’s Best Labor Day Getaways

Labor Day offers plenty of opportunities for fun, whether you’re looking for a place to escape the hoard of students that is about to descend upon the Boston metro area or you’re just looking for ways to have a great time during the long weekend. If you don’t have any backyard barbecues planned and don’t mind a bit of a drive then explore any of these fun festivals, tours, or getaway locations to make it a Labor Day you won’t be forgetting anytime soon.

Take a Lighthouse Brunch Cruise

Lighthouse Boston1 Long Wharf, Boston. Boarding begins at 11:30 AM.

If you’d like to treat yourself to a quiet, elegant day you can hardly go wrong with the Lighthouse Brunch Cruise. Sip on a Bloody Mary or enjoy the gourmet brunch bar as you sail lazily around the Boston Harbor. The cruise visits several historic lighthouses, including the Graves Light, the Deer Island Light, the Boston Light and the Long Island Light.


Party Hearty at the Pier Pressure White Yacht Party Cruise

200 Seaport Blvd, Boston. Check-in at 9:30 PM.

If you love the idea of getting out on the water but are something of a night owl you might prefer this raucous party cruise. Just remember that everyone has to wear white! Dance the night away with some of Boston’s hottest DJs and enjoy plenty of beautiful views of the Harbor at night, all within the lap of luxury.

Indulge Your Need for Speed at the Indy Car RaceBoston grand prix

Boston’s Seaport District

Watch some of the finest race cards whip around a 2.25 temporary street course which winds around the Convention and Exhibition Center. Get there early to choose the best spot along the track.

Enjoy Fun and Games at The Spencer Fair

48 Smithville Rd., Spencer, MA

There’s something for everyone at this traditional fair: animal shows, tractor pulls, live bands, contests, and more. If you’d like some good old fashioned, down home fun, this is the place to be.


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Enjoy the Performing Arts at the Boston Arts Festival

Christopher Columbus Park  

This annual festival features performances from over 60 solo artists and performance arts groups. That means live music in addition to dance and other performing arts. You can also buy art pieces from various vendors or even take a class on different techniques such as ceramics, or painting. The fun starts at 11 AM.

Get Out of Town

Maybe you just can’t stand the idea of the crowds and are hoping for a quiet weekend. If so, there are dozens of destinations within driving distance that will afford you a peaceful, beautiful weekend. This Vacation Idea article will give you a list of 21 inns and resorts to visit. You should also check out this list of 52 Weekend Trips and Getaways from Boston Magazine (they helpfully listed out all of the driving times to help you plan).

Whatever you choose to do, make the most of it…we’ll all be back at work soon enough.