Boston’s Biggest Annual Events

By Viator, July 2014

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For those who enjoy planning their trips around annual events, Boston is full of them. Whether you’re interested in wine, history, culture, food, film or something else, Boston has a festival for you. To help you plan a jubilant trip, here are some of Boston’s biggest annual events.

Boston Wine Festival

Said to be “America’s Longest Running Wine Festival,” the Boston Wine Festival begins the last week in January each year and continues for three-and-a-half months. During the event -- which takes place at the Boston Harbor Hotel -- regional wineries exhibit their products during tasting dinners prepared by local Chef Daniel Bruce, crafted specifically to compliment the wines. Interestingly, menus are never repeated. The festival also includes receptions, seminars and brunches. To continue exploring the city’s culinary and drinks scene, opt for one of the many great Boston food, wine and nightlife tours.


A week-long celebration of Boston’s maritime and colonial history Harborfest takes places during the first week in July and encompasses an array of smaller events, with the highlight being fireworks on July 4th at the Charles River Esplanade. During Harborfest another major highlight is Chowderfest, more commonly known as Chowdahfest -- where local restaurants compete to see who makes the best clam chowder. You’ll walk around to different booths sampling the various chowders before casting your vote. Other events during Boston’s Harborfest include a Rum and Revolution evening cruise; historical walking tours; live music; heritage-related exhibits; historical re-enactments; Boston Tea Party-themed scavenger hunts; colonial games; Freedom Trail walks; and more.

Phantom Gourmet Food Festival

For 10 years the Phantom Gourmet Food Festival has brought food, music, beer and entertainment to the people of Boston. The event, which happens in September and attracts about 10,000 people, features over 100 different dishes and samples are included in your ticket price ($40 in advance, $50 at the door). As the event is 21+, attendees can walk around the streets of the festival space freely with their wine and beer, hopping from venue to venue to see what special events are going on in honor of Phantom Gourmet.

Boston Film Festival

Taking place in September, the Boston Film Festival has been taking place for 29 years. Film categories include feature, documentary, animated and short, with the event showcasing talent from both up-and-coming and celebrated filmmakers. Some notable films that premiered at the festival include The Last Kiss, Kiss Kiss Bang Bang, North Country, Deliver Us From Evil, Jesus Camp and Renaissance. Along with seeing innovative films, attendees can go to panel discussions and Q&A sessions with producers, directors and actors. The Boston Film Festival is not to be confused with the Boston International Film Festival, which is also a worthwhile annual Boston event.  

The Boston Arts Festival

For those looking to discover Boston’s art and culture, the end of summer Boston Arts Festival started as a small one-day event back in 2006 and has grown into a three-day affair featuring both visual and performing arts and attracting about 50,000 people. An artist’s village is constructed especially for the festival -- which takes place in Christopher Columbus Park on Boston’s waterfront -- while about 20 performances are held. This makes it easy to spend your entire weekend immersed in art in a beautiful space. Tip: To further explore Boston art scene, check out the Boston Museum of Fine Arts which showcases impressive collections and artifacts from all over the world.

The Boston Marathon

Held on the third Monday in April every year, the 26-mile (42-kilometer) Boston Marathon is the oldest annual marathon in the world, taking place since 1897. While its beginnings saw only a handful of runners, today the event draws in 20,000 runners and half a million spectators. Despite 2013’s tragic bombing at the race, the Boston Marathon will continue its tradition into 2014. In fact, the Boston Athletic Association is inviting runners who couldn’t finish the 2013 race because of the bombings to run in 2014.

St. Patrick’s Day

Celebrating St. Patrick’s Day in Boston should be on everyone’s bucket list. The highlight of the event is the parade, which attracts 60,000 people each year, making it the second largest St. Patrick’s Day parade in the country (New York is the largest). Along with the parade, those attending St. Patrick’s Day in Boston can enjoy parties, pub crawls, the wild Paddy Fest, a traditional celebration at the Irish Cultural Centre of New England, Irish cooking classes at Le Cordon Bleu College of Culinary Art, and more.

Fourth of July

For those lucky enough to be in Boston for the Fourth of July, you’ll have plenty of options for things to do to celebrate. First of all, there is a fireworks display over the Charles River, which gives the already mesmerizing lights show a romantic touch. Onlookers can enjoy also live musical entertainment from the Boston Pops. Another option is to take a dinner cruise on Boston Harbor which allows you to indulge with delicious food and drinks while taking in the fireworks from the best seat in the house. The above-mentioned Harborfest is also going on during this time, so make sure to check out the events calendar to see what’s happening July 4th, as well as the days before and after.

Tours & Tickets

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Boston in One Day Sightseeing Tour, Boston, null

Boston in One Day Sightseeing Tour

4.5 star rating: Recommended 575 Reviews

Experience the very best of Boston in one day on this fully narrated sightseeing tour of the area's major sights. First, journey through the historic towns of ...  Read more

Location: Boston, Massachusetts
Duration: 7 hours (approx.)

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Boston TV and Movie Sites Walking Tour, Boston, Full-day Tours

Boston TV and Movie Sites Walking Tour

4.5 star rating: Recommended 3 Reviews

Tour the Boston Common and Beacon Hill areas and visit more than 30 movie locations on this captivating movie and TV walking tour! This tour is a must for film ...  Read more

Location: Boston, Massachusetts
Duration: 90 minutes (approx.)

From USD $25.00
Boston Ghosts and Gravestones Tour, Boston, Movie & TV Tours

Boston Ghosts and Gravestones Tour

4.5 star rating: Recommended 88 Reviews

Join other adventure seekers and become an apprentice grave digger on an entertaining tour through the darker side of Boston. A scary, fun and informative ...  Read more

Location: Boston, Massachusetts
Duration: 2 hours (approx.)

From USD $39.90

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