Head of the Charles

Even if you aren’t very interested in watching the regatta, there are a wealth of family friendly activities and vendors along the river. Head of the Charles is an Olympic qualifier, so be on the look out for a Team USA section. 2015 featured a mini Olympic museum on wheels and meet and greets with current Team USA gymnasts and swimmers.

Fun to watch! Teams go pretty often, so there isn’t much of a dull moment. Also lots of people and dog watching to be had!
If you’re rooting for a specific team or person, I suggest having a bike and going with them – I saw a few people doing that and it seemed like a great idea!

This is quintessential New England at its finest.
In a former, much younger life, I was a participant in this regatta twice. Back in the day, for a woman this was the ultimate race (aside from representing your country at the Olympics). The Henley, across the pond, has since opened up to women however this regatta is near and dear to all rowers’ hearts. There’s something quite special watching singles, doubles, fours, and eights power up the Charles. It is a difficult course to navigate, so it also challenges the coaches and coxswain to map out an efficient route that keeps the boat in one piece (yes you can crash those paper thin boats rather easily with a wide turn).
Now as a former rower, I love coming down and watching the spirit of competition and sportsmanship on display. You are able to get a surprisingly close view of the boats in action from the banks of the Charles, perhaps affording yourself an opportunity to pick up a thing or two about the sport. I’d suggest taking the T to Harvard Square and walking down to the Charles from there. Plenty of sponsors have booths and samples in this area. Bring a thermos with a warm (perhaps adult) beverage, a folding chair, and warm clothes to thoroughly enjoy the day. Weather in mid-​October is hit-​or-​miss, but it’s worth the trip. It’s FREE and you get experience one of the highest levels of competition that the sport can offer. Additionally, you can see young and old navigating the challenging course.
If you live here and haven’t been, make it a point for next year. If you are lucky enough to be in town visiting, it is a great way to spend some time in Cambridge experiencing a unique part of our great area.

Head of the Charles Regatta is an annual rowing event on the Charles River (between Boston & Cambridge). It’s a full weekend of crew teams from all over the country coming to compete, and thousands of spectators watching from the sides of the river.
I love coming to Head of the Charles to get in a good walk, and people watch.
It’s very pretty (Brooks Brothers had a huge booth this year) but also family and dog friendly. Spectators spread out down the race route, so it never feels to crowded.
There are lots of vendors selling food, and you often find free samples mixed in the booths — near the reunion village area of the race course.
I recommend checking out Head of the Charles even if you’ve never seen someone row before. You’ll still have fun and will be glad you saw what all the fuss is about.