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5 Spots for a Labor Day Getaway in Massachusetts

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Posted by Massachusetts Office of Travel and Tourism

The changing of the seasons officially takes place on September 23, although with school and work ramping back up as soon as the new month begins, it can sure feel like summer is on its way out as August ends.

But fret not! Before life gets busier again, Labor Day weekend will come and go, giving us all a chance to take in a few more days that embody summer’s true spirit.

For those still putting their long weekend plans together, here are five excellent places to spend it in Massachusetts.

Boston, MA

Boston typically needs little introduction as a travel destination, but Labor Day presents an especially suitable time for a trip. Not only is it a good chance to swing by before the chillier weather arrives, but there’s also plenty to see and do while in the area.

In Christopher Columbus Park, located right next to the Rose Kennedy Greenway, the appropriately named ähts: The Boston Arts Festival will take place on Saturday, August 30 and Sunday, August 31. On site will be all sorts of entertainment, ranging from musical performances to interactive activities to live art, as well as 45+ local craftsmen and women selling their work.


Photo: Rose Kennedy Greenway by Kindra Clineff

Labor Day weekend also happens to be the last few days that visitors can see the Magna Carta at the Museum of Fine Arts Boston, something that’s definitely worth a trip. When visiting the area, the Intercontinental Boston and Fairmont Battery Wharf are both good spots for an overnight.

Barnstable, MA

It’s always good to grab a bit more relaxation on Cape Cod before resuming the usual day-to-day, and this weekend will be a fun one in Barnstable. Throughout the summer, the Cape town has been celebrating its 375th anniversary with a number of commemorative events; on Saturday, August 30, visitors can explore two different special exhibits, and then settle in for some tunes, followed by a fireworks display at 8 p.m.

Beyond the 375 festivities, Sandy Neck Lighthouse is always cool to check out, and the eponymous beach park is a delightful place to spend the day. Those traveling to the area might consider a stay at the Beechwood Inn or Lamb and Lion Inn, which particularly attractive for travelers bringing furry friends.

Sandy Neck

Photo: Sandy Neck Lighthouse in Barnstable, MA by William DeSousa-Mauk

Gloucester, MA

Cool ocean air makes Gloucester an enviable place to be throughout the summer. For a special experience in this historic port city, Labor Day weekend is high time to visit. This coming weekend will welcome the annual Gloucester Schooner Festival, a celebration of maritime history and the unique role that the schooner has played throughout it.


Photo: Schooner Fame in Gloucester, MA

The festival runs from August 29 – 31, featuring concerts, fireworks, parades, a lobster bake, a walking tour and lots of sailing, of course. The annual Heritage Day celebration, which falls on Saturday, August 30, is definitely an event to circle, if your time is limited. To put your feet up in between the festivities, both the Harborview Inn and Gloucester Inn by the Sea are welcoming and right by the water.

Sturbridge, MA

Thanks to Old Sturbridge Village, this central Massachusetts town is a favorite destination for family-friendly fun, and the upcoming long weekend will have lots of it. First off, entry is free for kids aged 17 and under who are accompanied by an adult. After getting in, visitors will be treated to Family Fun Days through the whole weekend.


Photo: Toy fire-balloon flight at Old Sturbridge Village

During Family Fun Days, kids have a whole lot to choose from, including playing baseball with old-school rules, putting together a craft, joining in on tug-of-war and trying out some marbling paper. There will also be a puppet show, a toy fire-balloon taking flight and the chance to meet oxen in training. To make entry quick, it’s best to purchase tickets online, and multiple-day stays are made easy with lodgings on site.

Northampton, MA

Further west, the Three County Fair will get underway in Northampton right around the same time. The Three County Fair is one of several Massachusetts shindigs that began as a primarily agricultural gathering and has evolved through the years to become a whole lot more. Here’s a quick look at some of the highlights from last year’s festivities:

This year, the gates will open on August 29 and for four days of amusement rides, music, fleet-footed racing pigs, demolition derbies and more. There’ll be high-flying Frisbee dogs, too, of course. Directions to the fair are available online, and for anyone making a trip into the area, there’s no shortage of accommodations nearby, including the Historic College Inn, which is a ten-minute walk from the grounds.

For a look at more Labor Day fun all across the Commonwealth, just click here. You can also peruse Massachusetts events that take place throughout the entire year here.

Where do you like to spend Labor Day in Massachusetts? Let us know in the comments!

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