The Head of the Charles Regatta (#HOCR) is happening this weekend in Boston, and if you are anywhere near the Boston area, you have to go. The Head of the Charles was without a doubt my favorite fall weekend in Boston each year. During the three years I was at Harvard, the weather for each regatta was absolutely beautiful, and this year promises to be another gorgeous fall weekend! (Apparently last year it absolutely poured rain, so thank your lucky stars that there’s no rain in the forecast so far).
There’s something special and precious about this time of year in New England. It’s not too chilly yet, the sun is always shining, and the leaves are all nearing their peak color. There are only a few more weeks (if that) until it becomes dark and dreary and cold for the next five (…or six) months, so everyone wants to spend as much time outdoors as possible. The Head of the Charles comes at the perfect time, and everyone comes out to wander along the Charles, enjoy the sunshine, and watch the boats go by.
Plus, there are always lots of cute dogs at the Head of the Charles, which makes any event a 10 in my book.
I’m standing here on Weeks Bridge. You can see behind me the sea of tents selling food and Head of the Charles merchandise. Every year Brooks Brothers teams up with the regatta to offer the cutest Head of the Charles clothing. There are several main hubs of activities and vendors along the Charles River. You can check out the map here to see where everything will be located this year. This area behind me is directly down JFK from the Harvard T station and has tons of food stands and tents, so it’s a great place to start your HOCR day. If you cross the bridge behind me and keep walking for about 10 minutes, you’ll find an even bigger area near the finish line.
One of the great things about the Charles River is that you can literally walk right up to it, so you can find a nice spot of grass right at the water’s edge to watch the boats go by and enjoy a picnic.
The regatta includes college boats, but it also includes alumni boats, high school teams, and rowing clubs from across the country. One of the best parts of the weekend was always the chance to see friends who were in town for the regatta!
It’s always so fun to just wander up and down the river, people watching and taking everything in. The last year we were there we actually managed to stop in the Harvard Boathouse to watch a bit of the race! It was gorgeous and it looked like something straight out of the 1920s. Everyone was bustling around, excited for their races and cheering each other on. If only I wasn’t adverse to any activity that makes you wake up early and exercise in 30 degree weather… I would have never made it on the crew team!
Outside of the boathouse there was a little deck where people were hanging out to watch the races and cheer on the Crimson! 
The last few years the KJP team has teamed up with Brooks Brothers and hosted their own tent. I don’t think they’ll be here this year since Sarah is about to have her baby (!!), but you know it’s a good sign whenever an event is KJP and Vickers approved!
Their employees look like they’re in the middle of a photoshoot even when they’re just manning the shop… I mean, really, it’s not fair. I need to know their secrets!
I was lucky enough to run into Sarah Vickers a few years back at the Head of the Charles. She was so sweet to take a picture with me and it definitely made my day!
You’ll notice that in my photos there was one year when I was wearing my Barbour and boots, and another year when I was wearing shorts. It can still be really warm in Cambridge in October, so you need to check the weather before you let your fall outfit #goals run wild! This weekend it’s supposed to be in the mid- to- high 70s! Even though everyone (especially bloggers) loves to break out their fall scarves and boots and sweaters for HOCR, it’s usually not actually cold enough for all of that, so even if you look super cute, you’ll probably feel a little sweaty after walking up and down the Charles in the sun all day!
In addition to watching the boats go by, it’s also a beautiful weekend to just wander around Cambridge and Harvard Square.
Look at those leaves! And if you possibly needed any more reason to visit the Head of the Charles and Cambridge this weekend…
This is what Harvard Yard looks like in the fall.
If you’re going to be at the Head of the Charles this weekend there are a ton of places in Harvard Square to grab dinner and drinks afterwards (heads up- you should try to make reservations if you can because it’s packed during the Head of the Charles weekend). Some of my absolute favorite places are the rooftop deck at Daedalus, Park, Russel House Tavern, and John Harvard’s. And if you’re really looking for a good time you can always pretend you’re a college student again and visit the Kong-it’s your classic, crazy college bar, and it’s guaranteed to be a party on Saturday night!
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