3. Watch the world’s largest regatta before checking out Harvard Square (Cambridge, MA)
You already know that you’re deep in the heart of Ivy League country, so why not check out an athletic event featuring the quintessentially prep-school sport of rowing?
The Head of the Charles regatta, which takes place every year during one of the last weekends in October, isn’t just the world’s largest two-day rowing event, it’s a great place to grab a few beers and enjoy the crisp fall weather. We recommend grabbing a spot on one of the river’s many bridges—not only will you have snagged one of the best seats in the house, there’s a good chance you’ll see more than a few boats collide on the notoriously difficult (and often crowded) race course.
After a few hours of spectating—or if you’re not in town on Head of the Charles weekend—take the short walk over to Harvard Square, where you can grab a bite at Beat Brasserie, Alden & Harlow, or the appropriately themed Boathouse pub on Mt. Auburn St.
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