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Autumn in Boston: The Events you Can't Miss

By Mike Stapley

21 October 2026

If you’re visiting Boston it wouldn’t have escaped your notice that you’re in one of America’s most beautiful cities.  It’s a blend of the historical and the modern, with beautiful natural features and stunning hotels and restaurants.  It’s also helped by the fact that there’s plenty to do all year round.  Whether you live in ‘the walking city’ or are visiting as a tourist, possibly staying in a hotel, hostel or serviced apartment in Boston, autumn is a great time to be here.

The fall brings the famous foliage to Boston and the rest of New England, but what other events are taking place at this time of year?

Boston Columbus Day Parade

The Columbus Day Parade in the city sets out to celebrate on a number of fronts.  It of course marks Christopher Columbus’s exhibitions to the Americas but it also celebrates the Italian heritage to be found in Boston as well as thanking military personnel and their contribution to US freedom.

The parade itself is an eclectic mix of celebrations and that is reflected by what’s on show. Marching bands, different units from the military, organisations from the Italian-American community, floats of all shapes and sizes, entertainment, vintage cars and much more.

You might even catch some politicians and bagpipes too, if either of those are your thing?

Be aware the parade starts at different points depending on the year.  In odd numbered years it starts at the City Hall Plaza, in even numbered years it commences at Suffolk Downs parking lot.

Fort Point Open Studios

If art is more your thing then this event is certainly not to be missed.  Start off by visiting the Fort Point Art Community Gallery which is situated at 300 Congress Street.  Here you’ll be given a map which will detail the location of 150 art studios in the local area which are opening ip their doors or putting on special events.

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Local artists will be available to chat to and art will of course be available to buy.

Most are located in 14 known local art venues but other things to see will be featured at pop up stands and stages.  All of this takes place over three days every October and is absolutely free.

Boston Halloween Pumpkin Float

Nowhere in the world is Halloween celebrated quite like it is in the US and Boston is no exception.  However, Boston does put its own spin on proceedings with this unusual event.

pumpkin

It takes place at the Frog Pond on Boston Common and you’ll find all sorts of family activities available, as well as food and drink, refreshments and plenty of music and entertainment.

All you’re asked to do is to dress up in a Halloween costume and bring a small pumpkin with you (no bigger than 8 inches). It will then be lit and set afloat on the frog pond to complete a fantastic display.

Just remember to hollow out your pumpkin, it won’t float otherwise!

FAQs

What are the best things to do in Boston in the fall?

The best things to do in Boston in the fall include seeing the foliage in Boston Common and the Public Garden, walking Beacon Hill, exploring the Charles River Esplanade, attending seasonal events and taking a day trip to Salem.

When is the best time to see fall foliage in Boston?

The best time to see fall foliage in Boston is generally mid to late October, although the exact peak varies each year. September can offer early colour, while some areas may retain foliage into early November.

What are the best fall events in Boston?

Popular fall events in Boston include the Head of the Charles Regatta, Boston Book Festival, Oktoberfest celebrations, Halloween events and seasonal foliage activities. Event dates vary each year, so check the latest schedules before visiting.

Is October a good time to visit Boston?

Yes. October is one of the best months to visit Boston, with autumn foliage, cooler weather and major seasonal events including the Head of the Charles Regatta. It is also one of the busiest and more expensive periods to visit.

What is Boston like in November?

Boston in November is cooler and quieter than October, with fewer foliage events but plenty of museums, historic attractions, restaurants and late-autumn activities. Some outdoor seasonal attractions may have already ended.

Is Salem worth visiting from Boston in the fall?

Yes. Salem is one of the most popular fall day trips from Boston, particularly in October during Haunted Happenings. The journey takes about 30 minutes by MBTA Commuter Rail from North Station, although October weekends can be extremely busy.


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