October 17-19, 2025
Mid-October in Boston means crisp fall air, peak foliage, and one of the city’s most iconic events, the Head of the Charles Regatta. This year marks the 60th anniversary of the world’s largest three-day rowing competition, drawing over 11,750 athletes from nearly 900 clubs worldwide and 300,000+ spectators to the Charles River.
Whether you’re a rowing fan or just looking for a quintessential fall weekend in Boston, here’s everything you need to know.
What Is the Head of the Charles?
In 1965, members of the Cambridge Boat Club created a “processional” race modeled after England’s head races, thinking it might be a one-time thing. Six decades later, it’s Boston’s second-largest sporting event and a defining autumn tradition.
Athletes race single-file against the clock along a challenging 3-mile upstream course from Boston University’s DeWolfe Boathouse to Herter Park in Brighton. The course includes seven bridges and the legendary 90-degree turn at the Weeks Footbridge, one of the most technically demanding sections in competitive rowing.
When: Friday, Oct 17 (7:45am-11am) | Saturday & Sunday, Oct 18-19 (7:45am-late afternoon)
Best Viewing Spots
You can watch for free from almost anywhere along the course. Here’s where to go:
The Bridges – All six bridges offer elevated views. The BU Bridge shows the start line and smooth rowing. The Weeks Footbridge delivers the most dramatic action as crews navigate that challenging turn. The Anderson and Eliot Bridges showcase the approach to the finish. Arrive early, the bridges fill up fast.
Magazine Beach – Near the start line in Cambridge, this quieter spot offers space for families and a relaxed viewing experience.
The Weld Exhibition – Between Weeks Footbridge and Anderson Bridge (7-minute walk from Harvard Square), this is festival central with 30+ local food and beverage vendors. Perfect if you want the full event atmosphere.
The Riverbender – New this year on the Cambridge side, this area offers drinks, a DJ, lounge seating, and lawn games. Great for the social scene.
Herter Park – Watch crews cross the finish line and catch award ceremonies at Attager Row. The Expo features 40+ vendors with regatta merchandise, and the FALS Bar offers an outdoor beer garden viewing area.
Pro tip: Wear walking shoes and move along the course rather than staying in one spot. You’ll experience different race stages and atmospheres.
Getting There: Skip the Car
Memorial Drive from Cambridge Boat Club to Western Avenue closes Saturday and Sunday, 8am-7pm. Parking is extremely limited.
Best option: Take the T. Harvard and Central (Red Line) or BU Central (Green Line) are all within walking distance. Yes, it’ll be crowded, but you’ll avoid all traffic headaches.
Must drive? Reserve parking ahead through SpotHero. About 500 spots available at Harvard Stadium for $30/day, but they sell out.
Where to Eat: Local Favorites
Cambridge
- Monteverdi (Royal Sonesta) – Modern Italian with Charles River views
- Bar Enza (Charles Hotel) – Contemporary Italian in Harvard Square
- Geppetto (Cambridge Crossing) – Northern Italian from chef Will Gilson
- Row 34 (Kendall Square) – Outstanding oysters and lobster rolls
- Alden & Harlow (Brattle Street) – Thoughtful American cuisine in a cozy space
Boston
- 1928 Beacon Hill – Seasonal American with speakeasy vibes
- 75 Chestnut (Beacon Hill) – Regional American, neighborhood favorite for 20+ years
More to Do This Weekend
Fort Point Open Studios (Oct 17-19)
Boston’s original open studios event returns to historic Fort Point warehouses. Over 150 local and visiting artists open their doors with free workshops, live music, and performances. It’s the 45th anniversary this year.
When: Friday 4-7pm | Saturday & Sunday 12-6pm
Where: Fort Point, South Boston
Cost: Free
More info
The Yard’s Fall Festival (Oct 18-19)
Apple cider donuts, hayrides, live music, and seasonal activities at The Yard in Charlestown’s Hood Park. Family-friendly fall fun close to the city.
When: Saturday & Sunday, 11am-5pm
Where: Hood Park, 100 Hood Park Drive, Charlestown
Cost: $10 (kids under 12), $15 (adults)
Get tickets
Quick Tips
- Dress in layers – October weather in Boston is unpredictable
- Bring a camera – Peak foliage + river action = incredible photos
- Check the schedule – Visit hocr.org for race times and event details
- Stay for sunset – The fall light along the Charles is spectacular
Why It Matters
The Head of the Charles perfectly captures what makes Greater Boston special. The neighborhoods along the Charles, from Brighton and Allston through Cambridge to Beacon Hill, each bring their own character to the weekend. It’s world-class competition meets New England tradition, with vibrant local businesses and that quintessential fall beauty that reminds us why this area is so special.
Whether you’re a longtime resident or considering making the Boston area home, this weekend showcases the sense of community and seasonal celebrations that define life along the Charles River.
Looking to explore Boston and the Upper Cape? Follow The Mazur Team for local insights, market updates, and the inside scoop on what makes our communities special. Explore our resources.
