Families gather near "Reunion Village" on the Esplanade. Photo by 6SN7/CC BY 2.0

When to Go
Races run from 8am until 5pm on Saturday and Sunday. The most celebrated teams have their races at the end of each race day, which is undoubtedly an exciting experience. That said, if you have kids, you might want to consider going on Saturday morning, when there are fewer people and more room for running around.

The Weeks Footbridge is a popular spot to watch, but we share some less-crowded options. Photo by Scott Woolwine courtesy of Head Of The Charles®

Where to Sit
There is certainly no shortage of places from which to watch the shells race by, but some are better than others. My family likes to sit on the stretch of land between Mt. Auburn Hospital and the North Harvard St. bridge, where the crowds are few. If you feel the need for speed, check out the “Powerhouse Stretch” that leads into the River St. and Western Ave. bridges.

Watching from one of the many bridges gives you a bird’s eye view as the rowers pass beneath you. If you want to see crashes and clashes, try Elliot Bridge, which has seen plenty of confrontations in the Regatta’s history.

If you’re feeling adventurous, you could walk along the river and watch the races happen beside you. The course runs three miles upstream from the Boston University Boathouse to Christian Herter Park. It would take about an hour to walk, considering crowds and traffic, but allow yourself more time if you’re bringing your children.

If you’re not feeling adventurous, you can head to Reunion Village, which offers food and drinks under the safety of tents. The Village is halfway through the race on the Boston side, between the Weeks and Anderson bridges. In addition to having a great vantage point, there is a dining tent, seating, and a beer garden for the grownups. Passes are $10 per person, and free for kids under 12.

Pull up a seat—or a wagon, or stroller. Photo courtesy of Head Of The Charles®

What to Wear
I’m sure I don’t need to remind you, but late October in Boston could be 90 degrees or 40. Sadly, every time my family has gone to the Head of the Charles, it’s been closer to 40. So dress warmly. Bring the mittens and the hats, even if you don’t think you will need them. It gets windy by the river, and if there’s no sun and it’s already cold, you will thank me.

Check out the Head of Charles website before you go to recognize crews. Photo by Tom Stohlman/CC BY 2.0

How to Get There
Here is my most important tip: Please, for the love of all that is holy, do not drive to the river. Hundreds of thousands of other people will be in town for the Regatta, and it seems like each of them brought his own car. Parking is limited, and traffic gets tricky when Memorial Drive closes. Take this opportunity to walk, Uber, or take the T to get there, and you won’t regret it. Trust me.