Don't tell the other seasons, but Boston is most beautiful in the fall. When the cool air hits and the leaves start to turn, Boston's foliage puts on an unforgettable show that can be admired throughout the city. But, Boston's autumnal flair is attributed to far more than its breathtaking fall views. From cherished sporting events to spooky tours and everything in between, the Boston area has something for everyone this October. So, whether you're a local pretending to be a tourist in your own city or a visitor looking to experience an iconic New England fall, continue reading for a curated list of the top events in the Greater Boston area this October!

Top Events in October

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Boston's Wicked Haunt Fest Oct 07
  • 10 Stack St, Charlestown
  • Recurring daily

Boston, are you ready for spooky season?! Boston's Wicked Haunt Fest welcomes Halloween lovers of all ages to come experience the MAGIC of Halloween. The fest features a variety of themed areas and props, unique food items, themed bars, performance spaces, and…

Salem Haunted Happenings Oct 07

Welcome to Salem Haunted Happenings, the largest celebration of Halloween in the world! Salem is excited to welcome more than a half-million visitors to the parties, parades, vendor fairs, walking tours, museums, attractions, and special events. Plan ahead, put on your costume…

Fall Harvest Cruise Oct 19

Join us this fall to savor the tastes of fall on Cape Ann aboard our Harvest Cruises! Indulge in a flavorful buffet including Herb Crusted Prime Rib, Maple Mustard Herb Panko Crusted Chicken, Butternut Squash Ravioli, & more! Sip on your favorite seasonal cocktail, soak in…

Festival of Laughs Oct 11

The highly-anticipated FESTIVAL OF LAUGHS TOUR is coming to Boston featuring a diverse range of comedians, including Sommore (Netflix’s "Queen Chandelier"), Lavell Crawford (“Breaking Bad,” “Better Call Saul”), Tony Roberts (BET’s "Comic View") and Tony Rock (“Think Like A Man”)…

9th Curated Vintage Market at Bow Oct 13

Save the date for Bow’s fall Vintage Market! There will be 80+ vintage vendors from New England + beyond to bring the best & baddest vintage finds to the heart of Union Square, Somerville. Vendors will be on Somerville Ave & Bow Market. Come thirsty + come hungry + come…

Fall Crawl Oct 13

Join us on Sunday, October 13 for our Fall Crawl at Boston Landing! Think fall crafts, apple cider & timeless favorites like local craft beer, lawn games, and live music. Here’s what you need to know: 🍂 WHEN: Sunday, October 13th from 11a - 4p 🍂 WHERE: Athletes Park (92…

Titanic: The Artifact Exhibition Oct 17

Your Ticket Aboard Titanic Awaits. Experience the wonder and tragedy of the world’s most famous ocean-liner, RMS Titanic. Titanic: The Artifact Exhibition anchors in Boston this fall for a limited time at The Castle at Park Plaza. Viewed by more than 35 million people worldwide…

The Head Of The Charles Regatta Oct 18
  • Charles River, Cambridge
  • Recurring daily

Since 1965, rowers have come from near and far to take part in the world’s largest Regatta. But the fun isn’t limited to competitors. There are many ways for spectators to get involved in the weekend’s festivities. Whether you’re a first-timer or a seasoned veteran, the Regatta…

Revere Beach Pumpkin Dash Oct 19
  • Revere Beach, Across from Kelly's Roast Beef

The Revere Beach Partnership is pleased to present the Annual Great Pumpkin Dash 5K on October 19, 2024. The Revere Beach Pumpkin Dash is an exciting and festive community event that combines fitness, fun, and the spirit of the fall season. Participants of all ages come together…

Open Streets - Allston/Brighton Oct 20
  • Brighton Avenue and Harvard Avenue, Allston

Open Streets Boston is a free, family friendly event. During these events, the City will close major thoroughfares to motor traffic, opening them for pedestrian use including:​ walking, rolling, biking, and connecting with neighbors and local businesses. ​Open Streets Boston…

Boston Book Festival 2024 Oct 25
  • Copley Square

Celebrating the power of words to stimulate, agitate, unite, delight, and inspire, the Boston Book Festival presents year-round events culminating in an annual festival that promotes a culture of reading and ideas and enhances the vibrancy of our city. Find out more at…

Can't Miss Activities

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Plan Your Getaway

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