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- Visit Michelangelo’s Sistine Chapel: The Exhibition. Admire the timeless works of Michelangelo magnified 60x! The global exhibition will finally make its way to Boston this October after successful runs in London, Toronto, Shanghai, and NYC!
- Take a spooktacular mystery picnic with friends. What is a distinguishes a foodie from a mere mortal? Adventure! Enjoy the ultimate foodie adventure as your taste buds, and mind get to experience the thrill of a mystery picnic.
- Light up the mood with a candlelight concert. Imagine sitting in the warm glow of a thousand candles, with a live orchestra softly strumming classic tunes in an ornate historic building.
- Go apple picking at a tranquil orchard. Apple picking is the quintessential fall activity in New England. What’s better than exploring picturesque apple orchards, picking your own, and taking a bag home to enjoy in a homemade apple pie or just by themselves?
- The Public Gardens. If there’s one place to see fall foliage in Boston, it’s the Public Gardens. You’ll be able to enjoy colorful trees backdropped by the city skyline, take perfect fall photos on the pedestrian bridge, and see foliage at pretty much every turn in the park.
- Boston Common. Right next to the Public Gardens is Boston Common, which is another wonderful park in the city that’s a great spot to enjoy fall foliage colors.
- The Esplanade. One of my favorite walks in Boston year-round is the Esplanade, and it’s definitely the best in the fall season. A paved walkway along the Charles River, the Esplanade is packed with foliage color in the fall, and is such a lovely place to enjoy a crisp, autumn walk.
- Ghosts & Gravestones Trolley Tour. The Ghosts & Gravestones Trolley Tour is one of the most popular in the entire city, and for good reason! You’ll hop aboard a trolley at night to cruise around Boston with a costumed guide, and learn all about the spookiest hauntings around the city.
- Walk The Freedom Trail
- Get A Taste of Boston on A Food Tour
- Watch A Sports Game
- Explore The Boston Public Garden
- Explore Beacon Hill
- Grab A Beer at Oktoberfest
- Watch The Head of The Charles Regatta
- Head to A Pumpkin Patch
- Go on A Haunted Ghost Tour
- Take A Spooky Day Trip to Salem
Whether your trip to Boston is planned in the fall, winter, spring, or summer—you can’t miss the chance to take a guided walking tour of the Freedom Trail in Boston! It’s one of the best free things to do in Boston. The Freedom Trail is a 2.5-mile trail that leads you past notable sites from the American Revolution, like the Boston Common, Old Sout...
When you think of Boston, you might think of baked beans, clam chowder, and lobster rolls. Well, there’s a good reason why. Boston is well-known for its food, and one of the best ways to get a taste of the city’s best dishes is to go on a guided food tour. There are tons of food tours in Boston—from an Underground Donut Tour to the Bites of Boston ...
Bostonians love sports. If you’re a sports fan too, October is one of the best months to watch NFL, NHL, and MLB teams in action. If you have a car, you can make the drive to Gillette Stadium to watch the New England Patriots face off against another NFL team. However, you don’t have to leave town to watch professional sports games. The Boston Brui...
The Boston Public Garden is a gorgeous location for an autumn stroll when visiting Boston in October. There are tons of sites to see here, such as the “Make Way for Ducklings” Statue, Swan Boats, George Washington Statue, and more. In October, depending on the time of the month you’re visiting, you may be able to see the trees in the Boston Public ...
Walking around Beacon Hill is one of the best things to do in Bostonregardless of the season, but it’s especially charming in the fall. Beacon Hill is a beautiful, historic neighborhood that overlooks the Boston Common and Boston Public Garden. It’s always stunning in every season, however, in autumn, the colorful tree-lined streets, fall flowers, ...
Oktoberfest is celebrated during the first few weeks of October in several locations across Boston, MA—but the two most popular celebrations are in Harvard Square and at Harpoon Brewery. Oktoberfest in Harvard Square includes crafts, food, music, vintage goods, parades, and five beer gardens. Harpoon Brewery’s version of Oktoberfest includes dancin...
The Head of the Charles Regatta (HOCR) is the largest three-day regatta in the world—and it takes place on the Charles River in Boston, MA, every October. The HOCR includes over 10,000 athletes and nearly 2,00 boats participating in over 60 events! You can enjoy the events from several locations across the city, like the Boston University Bridge or...
There are tons of pumpkin patches in the suburbs of Boston, MA, where you can go pumpkin picking in October. Shelburne Farm, Boston Hill Farm, and Hanson’s Farm are a few of the most popular. While it might not be a good idea to pick a giant pumpkin if you need to fly home from Boston, if you’re driving home from the city, you can bring your pumpki...
If you’d like to discover the spooky side of Boston, consider going on the Ghosts and Gravestones Tour. This 1.5-hour nighttime tour will take you to graveyards across Boston, including Copp’s Hill Burying Ground and Granary Burying Ground. You can see the gravesites of John Hancock, Paul Revere, and Samuel Adams. Of course, the tour wouldn’t be co...
If the Ghosts and Gravestones Tour isn’t spooky enough, take a day trip to Salem, Massachusetts! Salem—the site of the infamous Salem Witch Trials in 1620—is just a 30-minute drive from Boston, making it the perfect place to visit in October and one of the best day trips from Boston. While in Salem, don’t miss the chance to visit the Salem Witch Mu...
- Brittany Sawyer
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- Oktoberfest. Oktoberfest is celebrated at various locations in Boston. Majorly expanded over the first couple of weeks, various locations have various activities in place, with music, food, dance, and of course- beer.
- Columbus Day Parade. Columbus Day Parade is one of the biggest celebrations in Boston. It celebrates Boston’s Italian history, the adventures of Christopher Columbus to America, and the commitment of Massachusetts military units to American freedom.
- Head of the Charles Regatta. The Head of the Charles Regatta (known as the HOCR), is the largest 2-day regatta in the world with over 11000 athletes, 1900 boats, and 61 events.
- Fall Foliage Cruise. Boston in October brings vibrant colors of fall to the scenery of the city. You can either take a walking tour or better yet, take a brunch or lunch cruise aboard the Northern Lights.
- Enjoy a spine-chilling Candlelight Concert. Get goosebumps from the spine-chilling serenade of a Candlelight Concert. Listen to your favorite cozy season tunes in the warm glow of thousands of candles.
- Explore Michelangelo’s Sistine Chapel: The Exhibition. Admire the masterpiece that is Michelangelo’s Sistine Chapel with vivid detail! Guest will have the opportunity to explore his work up close and personal with a life-size version of his work.
- Wander through vibrant sunflower fields. The best way to say goodbye to summer and hello to autumn is to stop by a sunflower field in full bloom. These flowers will look their best in early to mid September, so it’s the perfect seasonal activity to drive outside the city and have some fun in the gorgeous sunflowers!
- Enjoy a delicious apple cider donut from a local bakery. It’s that time of year when local orchards and bakeries start serving those steaming hot, cinnamon-dusted delicacies we call apple cider donuts.
Sep 26, 2023 · 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 things to do in the Greater Boston area this October!
Sep 29, 2023 · Oct. 1: Enjoy a day at the fair at The Big E. The first day of October is the final day of The Big E, officially called the Eastern States Exposition. Enjoy carnival rides, a circus spectacular,...
