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Prudential Center's 29th annual PruBoo
rachel lehman

The best things to do in Boston this weekend

From pop-ups to performances, each week we round up our favorite things to do in Boston for a fun weekend in the city.

JQ Louise
Katie McAleer
Written by
JQ Louise
&
Katie McAleer
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Halloween weekend is here, so order all the pumpkin spice and soak up spooky season. Luckily, there are plenty of fun things going on to keep us all busy this weekend in the city and nearby. But if nothing on this list sounds about right, check out the best cheap things to do or the best free things to do in Boston for fun all month long. When all else fails, rally up all of your friends for a boozy night out at one of the best bars in Boston.

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

Time Out Market Boston

Boston drag queen extraordinaire Plane Jane returns to Time Out Market on October 22 for Scary Movie Drag Bingo. Look out for wicked banter and outlandish costumes, and performances from Jane and a gaggle of her fiercest drag friends—and be sure to wear something stunning of your own; you know there’s going to be a costume contest. It’s all about the big-top vibes on October 28, when the market transforms into the Time Out Fun House, a massively fun spectacle with live DJs, high-flying circus performers, tarot readers and a fun 360 Photo booth.

Things to do in Boston this weekend

  • Things to do

Visit the Franklin Park Zoo October 28-29 10am-3pm for thrills, chills, animals and more at the annual Zoo Howl! This popular, family-friendly events includes the opportunity to trick-or-treat amongst the animals. Wear your best attire and you might just win the costume contest. As you enjoy the haunted happenings, be sure to meet with our educators who can tell you more about all the curious critters who call the zoo home. Learn more and get ticket information here.

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Leave your fears at the door and hit up Harvard Square for a Halloween-themed dinner party this Saturday October 29 at Harvest. Executive Chef Nick Deutmeyer and his crew are celebrating the holiday and the finest seasonal ingredients with event-exclusive treats and tricks. Festivities kick off at 6:30pm, get your tickets here.

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  • Things to do

The PruBoo is back Sunday, October 29, from 11am-1pm. The 29th annual event is a must-visit for little ghosts and goblins seeking a FREE family-friendly thrill this weekend. With over 50 participating stores, PruBoo has conjured up a whopping 4,550lbs of candy to be given away throughout the day. Kids can also enjoy face painting, pumpkin decorating, mind-blowing magic shows and an unforgettable concert. Visitors are encouraged to purchase a $5 trick-or-treat bag with all proceeds directly donated to the event’s non-profit partner, FARE (Food Allergy Research & Education). Even more bewitching, trick or treaters who stop by View Boston in costume receive a free same-day ticket. Accompanying adults get $5 off to enjoy the hauntingly beautiful views of the city from 750 ft above. Get all the details here.

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Join the Museum of Science for a Halloween-themed weekend! Festivities will include a dance party and family-friendly costume contest with special guest DJ Ooch, drop-in activities, design challenges and live presentations. Grab a passbook when you arrive and visit two or more activity stations throughout the day to win a special prize. Get all the details and purchase tickets here.

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  • Things to do

Open now through the end of the year, the new Converse Seaport Pop-up is offering interactive in-store customization, the latest in-season styles, exclusive limited-edition collaborations, and more. Get all the details here.

More things to do around 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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People visit New England every fall to see the gorgeous, colorful display that lights the region up with rich colors. Even if you’ve lived in the area your whole life, there’s no reason not to embrace the season, so get out and enjoy the vibrancy of autumn as much as possible, before the sad gray season shows up to put a damper on the fall foliage. You’ll definitely want to book a weekend getaway from Boston to see the leaves in other areas of New England or, if you’re visiting, to try a stay in a cozy Airbnb cabin near Boston. And don’t forget to pair your foliage adventures with the best hot chocolate in Boston to really get in the awesome out of autumn.

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

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  • Things to do

One of the most charming joys of fall in New England is ditching the city to head for an orchard to pick your own bag full of crunchy apples. A regional tradition like no other, apple-picking is a celebration of the season that brings us cozy sweaters, cider donuts, and crisp autumn air. If you’re looking to embrace the season within a reasonable distance from Boston, there are plenty of farms that welcome guests to wander the rows of their orchards and come home with plenty of fruit in tow. From Cortlands to Macouns and everything in between, here’s some spots to hunt down your favorite apples this autumn near Boston. As we enter those cozier autumn months, be sure to also check out where to see the best fall foliage in Boston, where to go hiking near Boston, where to go pumpkin picking near Boston and where to get the best hot chocolate in Boston.

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

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Can you feel the crisp autumn breeze cascading through your hair as you toss your scarf over your shoulder? If so, that means it’s New England in the fall, when the foliage is fiery and the apple cider is hot. While there’s countless activities that will let you bask in the beauty of autumn, pumpkin picking is a must-do for all card-carrying New Englanders and visitors alike. Ditch the pre-picked varieties at the grocery store checkout counter and head to one of these local farms near Boston, where you can hitch a ride on a wagon and choose your own stylish squash. For more seasonal activities, check out where to see the best fall foliage in Boston, where to go apple picking near Boston, and where to get the best hot chocolate in Boston.

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

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