Plan your vacation around these 5 must-see Boston events!
Boston is a city that celebrates in a big way, turning its historic streets and scenic waterways into massive annual stages. For first-time visitors, thereâs no better way to experience the cityâs heart than by planning your trip around one of Bostonâs signature events. From the electric cheers of the Boston Marathon on Patriotsâ Day and the massive St. Patrickâs Day Parade, to the neighborhood charm of Somerville PorchFest and the international spectacle of the Head of the Charles Regatta, these celebrations donât just draw crowds - they stop traffic. Each one offers a front-row seat to Bostonâs culture, community, and timeless energy. Whether you love history, sports, music, or neighborhood charm, these events showcase the city at its liveliest.
St. Patrick's Day
Bostonâs St. Patrickâs Day is one of the biggest celebrations in the country, and for good reason- the city has one of the largest Irish-American populations! Since 1901, South Boston has transformed into a sea of green for this legendary parade. Held on the Sunday closest to March 17 and lasting for 2 - 4 hours, the procession starts near Broadway Station in Cambridge, heads to West Broadway, loops around historic Dorchester Heights, and finishes near Andrew Station in South Boston. Expect enormous crowds, bagpipers, floats, and marching bands that fill the streets. Bars spill over with laughter and live music, families wave from sidewalks, and locals - Irish or not - proudly wear green (or their Celtics jersey). Itâs chaotic, it's heartfelt, and it's distinctly Boston.
Pro-tip: Take the MBTA Red Line, as the neighborhood is difficult to navigate by car.
Patriot's Day
On the third Monday of April each year, MA pauses to honor its revolutionary roots. Patriotsâ Day commemorates the first battles of the American Revolution at Lexington and Concord. The most famous reenactment occurs on Lexington Green around 5:30 am, when costumed actors recreate the dramatic âshot heard âround the world,â complete with musket fire, marching drums, and colonial uniforms that bring 1775 vividly to life. Following the action in Lexington, the focus shifts to Concord, where a second large-scale reenactment of the fight at the Old North Bridge takes place around 9:30 am. Crowds often gather hours before (some as early as 3:00 am!) to secure a good viewing spot along the greens and bridges. As the morning unfolds, towns across MA host parades, historical demonstrations, and community events that carry the revolutionary spirit through the day. Itâs a family-friendly, immersive experience that gives first-time visitors a rare chance to step into the past while feeling the pulse of a state that treasures its history.
Pro-tip: Head to Lexington Green for the dawn reenactment, then make your way back toward Boston to catch the Boston Marathon, which starts later that morning. Itâs one of the few days that you can literally experience both history and history in the making!
Boston Marathon
Also held on Patriotsâ Day, the Boston Marathon is the oldest annual marathon in the world and a bucket-list event for runners and spectators alike. Its significance goes far beyond its age: it is one of the six World Marathon Majors, attracting global superstar runners and offering an elite prize purse of more than $1.13 million, with the top Boston Marathon finishers in the menâs and womenâs divisions each receiving $150,000, making it a serious event for professional competitors. The first runners, including the elite wheelchair division, usually start just after 9:00 am, with professional runners and subsequent waves following shortly after, creating a full morning of staggered starts. The course is challenging- it starts from the Greater Boston suburb of Hopkinton, through the famed Heartbreak Hill in Newton, to downtown Boston, finishing on Boylston Street. Thereâd be thousands of cheering spectators that line the streets with waving signs, cowbells, and create a festival-like atmosphere that altogether electrifies the city.
Street closures and citywide celebrations make Marathon Monday a truly immersive experience. Locals and visitors alike join in the excitement, whether theyâre cheering for the elite runners or joining the sea of high-fives, community spirit, and marathon tradition.
Pro-tip: While spectators line the entire route, the best places to watch are crowd favorites where the energy is highest and the course offers crucial moments of action. Kenmore Square is known for its massive crowds, noise, and the final stretch excitement. Coolidge Corner marks the runners' arrival back into Boston, and the finish line area at Copley Square is the emotional epicenter of the day. If you don't want to hang out on the course, many local bars and restaurants near the route (especially in the Back Bay) host informal watch parties with televised coverage and special deals.
Somerville PorchFest
If you love music and community festivals, Somerville PorchFest is the perfect local outing. Held every May, usually around the 2nd weekend, this free neighborhood music festival transforms the porches, front yards, and small community spaces of Somerville homes into cozy performance stages. Spread across multiple streets and porches, the festival turns the entire neighborhood into a lively, walkable music stage, with performances happening simultaneously. Dozens of local musicians, from regular people who jam occasionally to those who have professional experience, perform for hundreds of visitors who wander from porch to porch, discovering everything from folk and indie to jazz and rock. The atmosphere is friendly, eclectic, and full of local charm, offering a one-of-a-kind way to experience Somervilleâs creative spirit and joie de vivre.
Pro-tip: Do not drive!
Head of the Charles Regatta
The Head of the Charles Regatta is the worldâs largest two-day rowing event, held every October, usually the third weekend, on the Charles River. Since its debut in 1965, the regatta has drawn more than 11,000 athletes from across the US and around the world, representing universities, clubs, and national teams. The three-mile course runs from Boston Universityâs DeWolfe Boathouse to Herter Park in Brighton. Along the riverbanks, spectators gather on blankets and folding chairs, soaking in the sound of oars slicing the water, coxswains shouting commands, and cheering crowds. With the crisp fall air and vibrant foliage overhead, itâs an immersive, festival-like experience that makes the regatta as exciting for first-time visitors as it is for seasoned rowing fans.
Pro-tip: The banks between Weeks Bridge and Eliot Bridge are popular vantage points.
