Massachusetts' Ivy-Clad Campus Is A Wonderland Of Fall Festivals, Markets, And Autumn Flavors

Set alongside the scenic Charles River in Cambridge, Harvard University truly comes alive in the fall. There's something magical about the leaves changing, and student or not, it's one of the best times to visit. Whether wandering through the pristine campus and taking in the vibrant foliage, attending a themed festival, or heading off campus for apple picking, there's no shortage of things to see and do.

Before setting out on your autumn adventure, it helps to have a lay of the land. Harvard Square is home to one of Massachusetts' liveliest street scenes, with trendy shops and food options, making it a good starting point for exploring the area. The square sits just outside the campus gates and is a main hub within Cambridge. In and around the square, you'll find dozens of restaurants, bars, cafes, and boutiques, as well as nearby landmarks like Harvard Yard.

Mount Auburn Cemetery and the Charles River Esplanade are two other spots to take in the colorful fall leaves in Cambridge. For a unique vantage point, consider signing up for a sightseeing boat tour along the Charles River. It's a great way to learn more about Cambridge's history while enjoying the changing leaves. 

Taking place every October, the Harvard Square Oktoberfest is a free event that always draws a crowd. Kick off the day with the HONK! Parade, which starts around 1 p.m. and features more than 25 street bands from across the country. Then, head to the festival's main stage for live music, or grab a crisp pint at one of the beer gardens. It's fun for the whole family, and there's even a dog-friendly wine garden.

The Head of the Charles Regatta is another October highlight in Cambridge. At the time of publication, the next race is scheduled for October 17–19, 2025. Many consider this the biggest rowing event in the world, drawing more than 11,000 athletes and hundreds of thousands of spectators. This year marks the race's 60th anniversary, making it an extra special one to witness. Watching the boats glide past the changing leaves is pretty striking.

For something more low-key, visit one of Cambridge's local farmers' markets. There are several to choose from, including the Central Square Farmers Market on Mondays, the Harvard University Farmers Market on Tuesdays, and the Charles River Farmers Market at Morse School on Saturdays. It's a great chance to meet local farmers and sample fresh, in-season produce. If time permits, consider taking a short drive to another thriving, artsy, walkable, and diverse gem just outside of Boston.

To reach Cambridge, look for flights landing at Boston Logan International Airport (BOS). From there, it's about a 20-minute drive without traffic. Alternatively, take the "T" to South Station and switch to the Red Line towards Alewife and get off at Harvard Square. It takes 45 minutes, and the outbound journey is actually free. 

While Cambridge is a very walkable city, renting a car is recommended for exploring the nearby area. In about 30 minutes by car, you can be at Belkin Family Lookout Farm, which is one of the oldest and most beloved farms in the country. After picking some apples, enjoy classic fare at their outdoor restaurant, The Lookout. If you're not the one driving, definitely try their famous hard cider. Slightly further out, you'll reach Russell Orchards. There's something for every interest here, whether it's visiting their winery, apple picking, or seeing farm animals up close at their barnyard. Traveling with the whole family? Here are a few of the easiest tips and tricks for making traveling with your kids a more stress-free experience.

As for where to stay, there are plenty of options to choose from. The Charles Hotel in Harvard Square is a popular pick on Booking, with reviewers noting clean rooms, friendly staff, and good value for money. For something a bit more bare bones, book a room at the Irving House at Harvard. It's a simple bed and breakfast ideal for families or extended stays.