Three Unique Fall Events in Boston

Boston is a great destination that offers great food, history and plenty of great events for visitors. The absolute best time to go to the New England region is in the fall, warm days, crisp and cool nights, beautiful fall leaves glowing in reds and yellows, caramel apples, and cider donuts.

I’m sure I’ve mentioned this before, but by far it’s my favorite time of the year. Granted, I could do without the leaf peepers clogging up the local highways, but since I am getting increasingly into photography, I might end up being a highway clogger myself this fall.

If you are thinking about taking a vacation to Boston, now is the time to do it! To help figure out just some of the great things to see in Boston, I’m giving you a mini guide here of three interesting and unique fall events that are happening in the next month.

Unique Fall Events

Head of the Charles Regatta

Head of the Charles

Held in late October every year, Head of the Charles is one of the biggest two day rowing events held in the world. Featuring athletes from high school to master seniors, this international competition attracts spectators who visit exhibitions, sample food and win free prizes. Boston swells by as much as an additional 300,000 visitors during this weekend. Even if you are not a fan of rowing or crew, it’s still a great atmosphere and a fun event to swing by and watch.

Boston Vegetarian Food Festival

Boston Vegetarian Food Festival

Running 24 years strong, this annual event held the last weekend in October offers cooking demonstrations, tastings, cookbook authors and national speakers all in one place advocating the benefits of a vegetarian diet. Boston has been a big player in the local slow food and veggie food movement and I don’t know about you, but I’ll go to pretty much any event that has food tastings and cooking demonstrations.

Pumpkin Chunkin

Is there a better way to celebrate the fall than catapulting pumpkins? Umm, no, obviously, the Pumpkin Chucking Festival is an annual fundraiser. On a side note, if you have not seen that show, check it out on YouTube or something, it’s pretty awesome these people spend all year long building these monster catapults that literally launch pumpkins hundreds of feet. I actually have attending the ‘official’ fest in Delaware on my own bucket list, and I recommend you putting it on yours as well, could there be a potential car pool in the future… Beyond the pumpkin tossing, this fest features food, and auction prizes for things like Patriots tickets.


So there you have it, of course there are other fun things going on in October in New England, like Oktoberfest (and I highly recommend you attend your local fest), but do a bit of searching and find some unique and fun things to hit up over the best time of year in New England.

If any of you guys have a fun and unique event that happens in your area, or you’ve been to a few interesting fests let me know, and we’ll make a list at some point.

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