A Boston Event for Every Month of the Year

A trip to Boston would not be complete without experiencing a local festival or event. Whatever time of year you find yourself exploring this city, don’t forget to include one of these quirky, historic, and delicious festivals into your plans.

Polar Plunge – January

If Boston is part of your plan for the new year, start it off in a fun way with the Polar Plunge. Every New Year’s Day since 1904, brave participants plunge into the icy waters of Boston Harbor. See it as a total body re-invigoration!

Wine and Food Expo – February

Sample over 1800 wines from around the world at this massive expo. A ticket gets you free wine samples and food pairings, as well as food demonstrations and wine seminars. A great event for anyone who wants to enjoy a glass, or five, of wine.

A South Boston St. Patrick’s Day – March

St. Patrick's Day Celebration

The Irish Culture is very prevalent in Southie (South Boston), and the St. Patrick’s Day parade is the second largest in the country. Celebrate this Irish holiday the right way, at a bar in South Boston with one million other revelers!

Boston Marathon – April

The third Monday in April each year is Boston Marathon Day, and the biggest sporting event in New England. Join 500,000 spectators to cheer on runners.

Duckling Day Parade – May

Boston Public Gardens

Photo by Karen Cunningham via trover.com

Each Mother’s Day, families recreate the book, Make Way for Ducklings, with a parade through Boston Public Garden. A seriously adorable way to celebrate moms.

The Scooper Bowl – June

3 days. 20 tons of ice cream. 60,000 participants.

The Scooper Bowl, aka the largest all-you-can-eat-ice cream event in the country, marks the beginning of summer. It is also a no guilt zone, as all proceeds go to charity.


Harborfest- July

Celebrate our nation’s independence at the largest July 4th Festival in the country. Events include a Boston Pops performance, historical reenactments, and harbor cruises. The events culminate with an astounding fireworks display.

Dine Out – August

Food lovers rejoice, Dine Out is Boston’s version of restaurant week. Hundreds of participating restaurants have fixed lunch and dinner options at three price levels. Each restaurant varies on how many courses served; all are delicious.

What the Fluff – September

In 1917, a Somerville (suburb of Boston) resident invented everyone’s favorite marshmallow gooey spread, Fluff. Celebrate this addicting dip with games, music, and of course, the delicious stuff itself.

Halloween in Salem – October

Salem, Massachusetts Halloween


Leave the city and head to spooky Salem for Halloween. The celebrations go on all month with costumed partygoers crowding the streets. Explore haunted buildings, get a psychic reading, or just enjoy watching the celebrations.

Thanksgiving at Plymouth – November

Celebrate Thanksgiving where it all began! The town of Plymouth hosts a festival and parade the weekend before Thanksgiving each year with concerts, historic walks and, of course, food!

Boston Tea Party Reenactment – December 

Boston Tea Party December Celebration

Photo by The Curious Zephyr via trover.com

Every December 16th re-enactors meet at the Old South Meeting House and march to the wharf where they dump tea into the water and relive a historic day for our nation.

It is important to note that some of these events bring in large crowds, so be sure to book your Boston hotel early!

This post is part of the Hipmunk #Citylove Campaign