Head of the Charles weekend is one of the best weekends of the year in Boston. The leaves are starting to turn along the river, the bridges are lined with people in their college scarves and the whole city feels a little more alive. The regatta runs October 16–18, 2026, and if you are coming in from out of town, now is the time to lock in your room. The best Head of the Charles hotels fill up months ahead, and the rooms that are left go quickly in October.
Here is where I would stay, where to watch and where to eat and drink once the racing is done.
About the Regatta
The Head of the Charles has been held since 1965 and is one of the largest rowing events in the world, drawing thousands of athletes and crowds of spectators to both sides of the river. The course runs about three miles upstream, from Boston University’s DeWolfe Boathouse to just past the Eliot Bridge, passing under six bridges along the way. It is free to watch from the riverbanks.
The Best Head of the Charles Hotels in Cambridge
The Charles Hotel. If you want to be in the middle of it, this is the one. It is in Harvard Square, an easy walk to the river and to the stretch between the Weeks Footbridge and the Eliot Bridge, where the most dramatic turns on the course happen. It is also the hotel I would choose for anyone visiting a student at Harvard that weekend.
The Royal Sonesta Boston. Set right on the Cambridge side of the Charles, near the Museum of Science, this is a good option for river views and easy access to both Cambridge and downtown. It sits downstream of the course, so plan on a car or the T to reach the racing.
Head of the Charles Hotels in Boston
Hotel Commonwealth. In Kenmore Square, close to the BU Bridge near the start of the course. I have written about it as a hotel for a Red Sox weekend, and it works just as well for the regatta, since you can walk to the river.
Mandarin Oriental Boston. For a more polished stay in the Back Bay, the Mandarin Oriental Boston on Boylston Street is one of my picks. You are a short ride from the river and right in the middle of Newbury Street shopping and dinner.
Four Seasons Hotel One Dalton. A great choice if you want a sleek, high-floor room with a view over the city. It is also home to LPM, which I wrote about in my review of LPM Restaurant Boston at Four Seasons One Dalton, so dinner can be downstairs.
Where to Watch the Races
Pick one spot and settle in rather than trying to follow every boat.
- Weeks Footbridge. This pedestrian bridge near Harvard is, in my opinion, the best place to watch. The turn here is tight and crews have to get it right.
- Eliot Bridge. Another sharp turn near the finish, where collisions are most likely.
- Herter Park. On the Boston side near the finish, with more room to spread out.
- The BU Bridge and Magazine Beach. Near the start, where you can watch crews line up and take off.
Where to Eat and Drink
After a day on the river, you will want a proper dinner and a good drink.
Hawksmoor Boston. The London steakhouse opened in Fort Point on September 8, and it is one of the biggest restaurant openings of the fall. Book it for a big group dinner on Saturday night. The Direct Martinis are served ice-cold at minus two degrees Fahrenheit, and on Sunday there is a classic British roast.
Kaia. For something lighter, Kaia in the South End serves Greek food with a lovely patio. On a sunny October afternoon it is the perfect place to recover from a day of cheering.
Harvard Square. If you are staying in Cambridge, there are plenty of cafés, bars and restaurants within walking distance of the river, which saves you fighting race traffic for dinner.
My Booking Tips for Regatta Weekend
- Book now. Head of the Charles hotels often require minimum stays and prices rise as the weekend gets closer. If your preferred hotel is sold out, call directly and ask about cancellations.
- Stay near the part of the course you care about. If you are following a specific crew, look up their start time and stay at that end of the river.
- Skip the car. Parking is limited and parts of Memorial Drive close during race weekend. Take the Red Line to Harvard or the Green Line to BU.
- Make dinner reservations early. Restaurants near the river and in the Back Bay fill up with teams, alumni and families.
- Dress in layers. Mornings on the river can be cold, and by the afternoon you may be down to a sweater.
For me, this is Boston at its best: crisp air, the river full of boats and a great dinner at the end of the day. For more on where to eat and drink in the city, see Santé Magazine.
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