Fall Events in Boston: Make Your Travel Plans Now

Boston in the fall is truly something special. The city comes alive with crisp autumn air, stunning foliage, and a packed calendar of events that draw visitors from near and far. Whether you’re planning a weekend getaway or a longer stay, now is the perfect time to book your trip and experience Boston in its most colorful season.

Why Visit Boston in the Fall?

Autumn in Boston is more than just pumpkin spice and cozy sweaters. It’s Red Sox games at Fenway, foliage tours along the Charles River, and lively festivals scattered throughout the city. The weather is ideal for exploring—cool enough for comfort, but still perfect for walking the historic streets of Beacon Hill, strolling through Boston Common, or hopping between events.

Can’t-Miss Fall Events in Boston

Here are just a few highlights to look forward to this season:

• Head of the Charles Regatta (October) – The world’s largest two-day rowing event, drawing athletes and spectators from across the globe.
• Boston Book Festival (October) – A literary celebration with author talks, readings, and activities across Copley Square.
• Fall Foliage & Ghost Tours – Nothing says Boston in the fall like walking tours through historic streets and legendary haunts.
• Food & Drink Festivals – From beer fests to harvest celebrations, Boston’s food scene shines in the fall.

(You can always check the city’s event calendar to see what’s happening during your visit.)

Make Our Pub Part of Your Fall Plans

No Boston trip is complete without spending time in Beacon Hill—one of the city’s most charming and historic neighborhoods. After a day of exploring events, sightseeing, or catching a game, stop by Cheers for a pint, a hearty meal, and the kind of warm atmosphere that makes fall in Boston unforgettable.

We’re just steps from Boston Common and the State House, making us the perfect spot to gather with friends, catch live sports, or simply unwind after a full day of fall fun.

So start planning your autumn getaway now—Boston is waiting, and we can’t wait to welcome you.