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The best things to do in Boston this weekend

Find the very best things to do in Boston this weekend—from live performances to cool cultural offerings

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Written by
Olivia Vanni
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Looking for the best things to do in Boston this weekend? We’re at your service. With so many events taking place across the city, we've sorted through all of your options and are sharing only our top recommendations for going out Friday, Saturday and Sunday. If nothing on our list here strikes your fancy, take a look at our guides to the best cheap things to do and best free things to do in Boston. Of course, it’s also autumn in New England, which means that you could always spend the weekend going apple picking, pumpkin picking or checking out the best fall foliage spots near Boston

RECOMMENDED: Full guide to the best things to do in Boston

Check out the action at Time Out Market Boston

  • Things to do
  • Events & Festivals

The leaves are changing, the air is crisping, and fall is officially upon us—and we folks at Time Out Market Boston will be celebrating the season in style with its Fall Festival in the Fenway this Saturday, Oct. 16 between noon and 10pm. We’re talking tastings with some of the best craft cideries in Massachusetts, seasonal donuts and food specials, and cocktails that taste just like autumn in a glass—all culminating in a nighttime screening of the cherished cult classic (and Salem-shot flick) Hocus Pocus.

  • Time Out Market
  • Fenway/Kenmore

Prepare to Play and Slay at Time Out Market Boston on Sunday, when we’ll be hosting an epic night of drag bingo. Plane Jane takes over the stage at 7pm! She’ll be gracing us with a short (but no doubt spectacular) number to kick off the hour-long bingo bonanza. Between rounds, you can expect “jaw-dropping, eye-popping, heart-throbbing and laughter-inducing entertainment” from Miss Jane, as well as appearances from fellow queens and prizes—we’re talking swag bags and Time Out Market Boston gift cards—between each round. The best part: It’s totally free to participate, so grab some food, some booze and a bingo card, and hunker down for a night of fabulousness and fun.

Things to do in Boston this weekend

  • Things to do

It basically isn't fall in New England until you're orchard-bound and apple picking. Each yearl this beloved regional tradition lets all of us celebrate the season to the fullest, allowing us to escape to nature, breathe in that crisp autumn air and load up on local fruit. Fortunately,you can visit these farms that are an easy drive away from Boston, all prime for our favorite fall activities like picking apples, sipping cider and eating fresh donuts, taking hayrides and petting adorable barnyard animals.

  • Things to do
  • Somerville

If you’ve ever screamed your way through a haunted house and thought, “But this could really use some beer,” then we’ve got the event for you. Aeronaut Brewing will be letting guests consume craft beverages and scare themselves silly by hosting some haunted brewery tours this weekend. Head to the Everett taproom and be guided your way through its creepified cannery, filled with “ghoulish ghosts of brewers past,” “monsters,” and “sinister spaces.” Tours will leave every 15 minutes, and tickets will be available for purchase at the top of every hour, giving folks ample opportunity to build up some liquid courage before they dare enter its spine-chilling spectacle. 

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  • Things to do
  • Seaport District

Make your way over the Fort Point Channel this weekend to shop til you drop at the Seaport x Black Owned Bos. Market, hosted by WS Development. More than 30 black-owned businesses from throughout Greater Boston and beyond will be popping up on Seaport Common (85 Northern Avenue) this Saturday and Sunday. A live DJ will be onsite to provide good vibes while you peruse these local entrepreneurs’ offerings, which span from skincare products and clothing to artwork and houseplants.

  • Things to do
  • Beacon Hill

Carrie Nation Cocktail Club wants you to drag yourself out of bed and into brunch this Sunday, when the downtown establishment will be hosting its beloved drag brunch. The fabulous festivities will be held between 2—4pm (perfect timing for folks who need a little extra sleep to recover from the night prior), when local favorites Destiny Boston and Dee Dee de Ray will get the crowd rowdy with the help of special guest performers. Pre-game the show with Carrie Nation’s brunch buffet spread, which will be up and running 12—2pm, and be sure to stay hydrated throughout the afternoon with its selection of specialty cocktails and full bar. You must purchase tickets in advance for this 21+ event, in addition to calling, texting or emailing the eatery to ensure your entire group can sit together at a table.

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  • Things to do
  • Events & Festivals

Oktoberfest—that glorious time of the year when you celebrate beer by downing stein after stein of this beautiful brewed libation. While the official festivities over in Munich, Germany, won’t be happening again this fall, there are plenty of places throughout Boston who are picking up the slack and throwing their own Bavarian-inspired bashes. Whether you’re looking to sip on seasonal craft beers or have a full-on German feast—here are the best local breweries and restaurants that will be hosting Oktoberfest events over the next month or so. 

  • Things to do
  • Somerville

Shakespearean plays can sometimes seem a bit stuffy—but not when there’s a super sloppy actor on stage. The Rockwell is bringing back its fan-favorite, Shit-faced Shakespeare, with its latest run of A Midsummer’s Night Dream. The production will be following The Bard’s classic comedy line by line, with just one exception: One of the players will be totally loaded the entire time. Come see the troupe and its designated drunk performer struggle their way through the play, which will include taking plenty of booze-fueled creative liberties, and get tipsy yourself at the Somerville theater’s inhouse bar.

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  • Things to do

Every October, floods of tourists fill the streets of Salem, MA, looking to get that fix of spooky fun right in time for Halloween. While the city is most known for being the site of the infamous Witch Trials, there's more to this Boston suburb than its dark history of hysteria and supposed sorcery. Here are the best things to do in Salem—ranging from the creepy and otherwise otherwordly, to the artsy and just plain normal.

More things to do around Boston

  • Things to do

After a long winter (and spring) enduring the cold—while occasionally enjoying the Boston’s best winter activities and best indoor activities—it’s time to get outside and soak up the sun. Whether it’s enjoying nature, taking in some historical sites, getting out on the water, attending an outdoor concert or having a picnic, there are plenty of top-notch summer activities in Boston. If you have little ones, check out our lists of the best things to do with kids in Boston and the best beaches in the Boston area

RECOMMENDED: Full guide to the best things to do in Boston

The 50 best things to do in Boston
  • Things to do

No matter where your interests lie, you can always find something to get excited about in the Hub. The best things to do in Boston run the gamut—from seriously fun to awesomely educational.

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