Our Favorite List of Activities in Boston for Fall

Fall is the time of year when the leaves embrace the ground and the skies turn orange as the cool breeze finally sets in. In Boston, there are plenty of activities you can enjoy during the fall season. As a tourist or as a member of the city Boston, you can see the sights and enroll in many of the events happening during this chilly season.


There are places you can go in the fall, to find yourself some ‘me’ time. Enjoy the sights and festivities of fall with your friends in some of the Boston destinations.


  • One of the stellar events hosted in Boston around the fall season is the Charles Regatta. This two-day rowing race is one that brings all of the best athletes together to compete. This year will mark the 54th anniversary of this competition. 


Of course, not everyone comes to compete, and if this is your case, then you can join the 300,000 spectators that come to watch this race every year. This event is held on the 3rd weekend of October.


  • Another pleasant activity for the fall season is bike riding. Don’t just grab your bike and stroll around, enlist in a tour group and see Boston with a fresh set of eyes. You don’t have to worry about booking a tour in time, there’s always a tour ready to go in Boston. Choose a time and day convenient for you and you’re good to go. Tours can be from $35 to $65 per person.


  • Want a great day out in the sun with your friends? Then look no further than the City Winery on the Greenway. Located at Dewey Square, you can visit it anytime on Mondays, Wednesdays, Fridays, Saturdays, and Sundays, in between the months of May and October.


  • This year, enjoy the delightful Downton Abbey; The Exhibition visits Boston in autumn. Taking place at The Castle at Park Plaza, 130 Columbus Ave, you can book your tickets now for an exclusive experience. Walk into post-Edwardian England through the shoes of your favorite characters from 10 am to 6 pm. It ends on September 29th, so move fast!



Outings with children can be tricky. Where to take them? What will they be interested in? Where can they learn and have fun?

Luckily, there are places in Boston where your kids can enjoy their own sights and games. Here are some of the events you can take your children to, to let some energy go. 


  • There are always the classics open all year round you can cherish with your kids, showing and teaching them all the fun things in life. One of such places is the New England Aquarium. With your Go Boston pass, you can enter for free. You can see penguins, snakes, seals, and much more. You can even get up close and touch sharks and rays in the touch tank.


  • Another treat to add to the list is the Boston Children’s Museum. Once again, with a Go Boston pass, you can enter for free and receive history from your local guide. There is hands-on fun for children; they can run through a giant maze, climb over walls, and create art for their own memories. There are new events and presentations taking place at this museum, so check the schedule before you plan your trip.


There are always times when you want the whole family to come together and enjoy the oncoming chilly season of autumn as one.


  • On October 18th, bring your family along to the Boston Common Frog Park where the 6th Annual Pumpkin Float will take place. It’s a wonderful event hosted by Boston Parks and Recreation, partnered with The Skating Club of Boston.


In this special event, you can enjoy free fun, refreshments, and entertainment targeted to appeal to your kids. You can bring your own carved pumpkin and watch it sail around the pond amongst hundreds of other participants.


  • The Boston Freedom Trail Walking Tour is a great family event you can book. You can even get free access to your tour with the Go Boston pass. Behind 18th Century practitioners, you can get the full experience and knowledge of Boston’s most historic sights, and memoirs from the American Revolution. The trail starts in Boston Common and ends in Charlestown.


  • For two days in Boston, there is the Boston Book Festival to look forward to. On October 19th, the book fair will be in Copley Square. On the 20th, it’ll move to Roxbury, and authors will be coming to the book fair during specific hours. 


  • Finally, there’s an all-round favorite activity, apple picking! At local and designated farms, you’re allowed to come in and pick your own apples! Bring your children and enjoy the cool weather yourself as you go through this year’s pickings. Farms such as Shelburne are open to the public.

Final Thoughts

There is so much to do in Boston in the fall season, and all year around. Take some time out of your schedule, and find fun times in everything Boston has to offer before the snow settles and the time is gone!