Boston, a city rich in history and culture, offers a vibrant array of annual events that captivate locals and tourists alike.
From iconic marathons to festive parades, the city’s calendar is packed with activities that celebrate its unique heritage and community spirit.
Whether you’re a sports enthusiast, a history buff, or someone who loves a good party, Boston has something for everyone.
Dive into this guide to discover the top 10 best annual events in Boston and start planning your next visit to experience the city at its finest.
Top Top 10 Best Annual Events in Boston
Boston is known for its vibrant culture and rich history, which is reflected in its many annual events.
Here are ten of the best annual events you should consider experiencing:
1. Boston Blooms Block Party
Boston Blooms Block Party is a springtime festival in Downtown Boston that occurs every April. It gathers employees, residents, and visitors for a day filled with festivities.
Last year’s event was a hit, featuring food trucks, live music, art installations, and a pop-up beer garden.
Attendees can enjoy local cuisine from various food trucks and dance to live music performances.
Art lovers can explore interactive displays, and adults can unwind at the beer garden. Though the event’s 2024 date hasn’t been set, its past success suggests it will return this year.
2. Brookline Springfest
Brookline Springfest happens every May in Olmsted Park. This annual community gathering celebrates trees with the kickoff of the Town’s Urban Forest Climate Resiliency Master Plan. It includes family-friendly activities and an Arbor Day planting and proclamation.
Attendees can enjoy a variety of activities. Yard games, crafting stations, and scavenger hunts are popular among families. Food vendors offer a range of delicious options, ensuring no one leaves hungry.
Live music provides a festive atmosphere. Local bands and musicians add to the charm of the event, making it a memorable experience for all. The Brookline Springfest is a perfect blend of community spirit and environmental awareness.
3. Wake Up The Earth Festival
Held every May in Jamaica Plain, the “Wake Up The Earth” Festival is a celebration of community, diversity, and activism.
This annual event began in 1979, commemorating the successful grassroots movement that stopped the Highway (I-95) construction. The festival features local artists and performers, offering a vibrant mix of music and dance.
The festival kicks off with a colorful parade and takes place at the Southwest Corridor next to the Stony Brook T. Attendees can enjoy various performances, food vendors, and interactive activities.
It’s not only a celebration of spring but also an appreciation of the land preserved from highway construction, embodying community resilience and environmental activism.
4. Let’s Dance Boston! Rose Kennedy Greenway
Let’s Dance Boston is one of Boston’s largest free outdoor dance and music parties, lighting up the Rose Kennedy Greenway in May.
Spanning five consecutive nights, this event features diverse dance styles like salsa, swing, and ballroom. Free dance lessons, live music, and open dancing make it accessible to all ages and skill levels.
The festival fosters community spirit, welcoming warmer weather in a beautiful outdoor setting. Food trucks on-site ensure attendees can enjoy delicious bites while dancing the night away.
Get ready to move and groove, with each evening bringing a new, electrifying vibe to Boston’s iconic greenspace.
5. Lilac Festival Arnold Arboretum
The Lilac Festival at Arnold Arboretum is a beloved Boston tradition, held annually on the second Sunday in May. For 2024, it’s scheduled for May 14.
This event celebrates the blooming of over 380 lilac plants, offering a visual and aromatic feast for attendees.
Visitors can enjoy guided tours of the lilac collection, providing insights into the history and horticulture of this beautiful flower.
Families and friends gather to picnic, as it’s the only day picnicking is officially allowed in the Arboretum.
There’s also a variety of food and crafts vendors, children’s activities, and live music, making it a festive and educational outing. The Arnold Arboretum’s natural beauty enhances this day-long celebration of spring.
6. Duckling Day
Duckling Day is a cherished Boston tradition celebrated for over 30 years every May. Inspired by the beloved children’s book “Make Way for Ducklings”, this event features a delightful parade through Boston Common parks.
Children and their parents dress as their favorite characters and enjoy the picturesque surroundings.
The Harvard Marching Band leads the parade, creating a festive atmosphere. Families are encouraged to decorate their wagons or strollers, adding a personal touch to the celebration.
The event culminates in a delightful gathering where families can share a picnic, meet others, and revel in the joy of spring.
Duckling Day is a quintessential way to experience Boston’s vibrant community spirit, making it a must-visit event for families.
7. Glow in the Park Rose Kennedy Greenway
Glow in the Park lights up the Rose Kennedy Greenway every June, kicking off summer in Boston.
This dazzling festival features vibrant live music, stunning light installations, and interactive lawn games. Boston’s best food and drink vendors offer delicious options to satisfy every palate.
Attendees can dive into the glow-in-the-dark experience with glow sticks and glowing hair and make-up, courtesy of Glamsquad.
It’s the perfect night to dance under the stars with friends, backed by energetic music. Tickets are required, and donations support the Greenway Conservancy, emphasizing community participation and support.
Join this luminous event for an unforgettable night that blends art, music, and community spirit.
8. Boston Dragon Boat Festival
The Boston Dragon Boat Festival, one of North America’s oldest, happens every June. 50 teams paddle vividly colored dragon boats down the Charles River, making it a spectacular event.
Memorial Drive in Cambridge becomes a hub of activity, offering cultural performances, food, and crafts, all for free. Spectators flock to witness the thrilling dragon boat races and to indulge in the cultural festivities.
This family-friendly event is perfect for experiencing Boston’s unique cultural blend while enjoying a day by the river. The Boston Marathon, held every April, is another must-see event.
It attracts runners and spectators from around the globe, showcasing endurance and community spirit. With its historic route and enthusiastic crowd support, this race is more than just a sporting event; it’s a celebration of resilience and determination.
The marathon brings together people from all walks of life, embodying the relentless spirit of Boston in every stride.
9. Save The Harbor Beach Bash – Constitution Beach, Piers Park
Save The Harbor Beach Bash is a highlight of Eastie Week in July, celebrated at Constitution Beach, Piers Park. This event draws the community together with live music, food, and family-friendly entertainment.
Beach activities include crabbing, fishing, and swimming, providing fun for all ages. Hosted by Save The Harbor, the Beach Bash also serves as a fundraiser to raise awareness about preserving Boston Harbor.
Families and friends gather to enjoy the vibrant atmosphere, making it a must-visit event in Boston’s summer calendar.
Don’t miss this engaging celebration that underscores the importance of protecting natural resources.
10. Puerto Rican Festival – Franklin Park
The Puerto Rican Festival in Franklin Park, Boston, happens every July, celebrating Puerto Rican culture and community.
This event, organized by the Franklin Park Coalition, highlights vibrant live music and dance performances, creating an infectious energy.
Visitors can savor delicious Puerto Rican food, explore arts and crafts vendors, and enjoy numerous activities for children.
The festival also features one of Boston’s largest parades, complete with marching twirlers, colorful dance troupes, bands, and musical floats.
This engaging parade draws participants and spectators from across the city, offering a festive and educational experience.
A must-attend for anyone looking to immerse themselves in Puerto Rican culture, the Puerto Rican Festival is a lively addition to Boston’s summer events.
Things to Consider for Enjoying Annual Events in Boston
Attending annual events in Boston can be a fantastic experience, but to make the most of it, there are a few things to consider.
Here’s a guide to help you enjoy these events to the fullest:
Plan Ahead
Popular events can sell out quickly or have limited capacity. Check event websites for dates, ticket availability, and any early-bird specials. Book accommodations and transportation well in advance, especially during peak seasons.
Arrive Early
Arriving early can help you secure a good spot and avoid long lines. For large events like the Boston Marathon or fireworks display, plan to get there a few hours before the start to find parking, settle in, and soak up the atmosphere.
Check the Weather
Boston weather can be unpredictable, especially in transitional seasons. Look up the forecast before you head out and dress accordingly. For outdoor events, consider bringing layers, rain gear, and sun protection.
Transportation and Parking
Traffic and parking can be challenging during big events. Use public transportation when possible, as it’s often more convenient and cost-effective.
Check for any event-specific transportation services or road closures. If driving, arrive early to find parking or consider using a ride-sharing service.
Stay Hydrated and Nourished
Events, especially outdoor ones, can be physically demanding. Bring a refillable water bottle and snacks. Many events have food vendors, but lines can be long, so having some essentials on hand can be helpful.
Know the Event Details
Understanding the schedule and layout can enhance your experience. Review the event itinerary and map before you go. Knowing where the stages, restrooms, and first aid stations are can save you time and hassle.
Dress Comfortably
You may be on your feet for long periods or exposed to various weather conditions. Wear comfortable shoes and dress in layers. If attending an event like a film festival or a gala, check the dress code and dress accordingly.
Respect Local Guidelines and Regulations
Boston events often have specific rules and guidelines for safety and enjoyment. Familiarize yourself with any event-specific rules regarding items you can bring, such as large bags or umbrellas. Follow any health and safety protocols in place.
Engage with the Community
Events are a great opportunity to meet people and experience local culture. Participate in activities, visit local booths, and interact with other attendees. Engaging with the event’s community aspect can enhance your overall experience.
Capture the Moment
Annual events can offer memorable experiences. Bring a camera or use your smartphone to capture special moments. Remember to be considerate of others when taking photos, and respect any event restrictions on photography.
Be Prepared for Crowds
Many of Boston’s annual events draw large crowds. Be patient and flexible. Arrive early to avoid the heaviest crowds, and plan for possible delays or longer wait times.
Check for Accessibility Options
Some events may have specific needs for accessibility. If you have mobility issues or other special requirements, check the event’s accessibility options and contact organizers if needed.
Frequently Asked Questions
When is the Boston Blooms Block Party held?
The Boston Blooms Block Party is held every April in Downtown Boston. Although the date for the 2024 event has not been announced, it is expected to take place due to its past success.
What activities can I enjoy at the Brookline Springfest?
At Brookline Springfest, you can enjoy family-friendly activities, food options from local vendors, live music from local bands, and community celebrations centered around trees and urban forest climate resiliency.
What is Wake Up The Earth Festival about?
Wake Up The Earth Festival, held every May in Jamaica Plain, celebrates community, diversity, and activism with local artists, a colorful parade, and various performances and food vendors.
What is special about the Lilac Festival at Arnold Arboretum?
The Lilac Festival at Arnold Arboretum, held annually on the second Sunday in May, celebrates the blooming of over 380 lilac plants with guided tours, picnicking, and children’s activities.
What can families do at Duckling Day?
During Duckling Day, families can participate in a parade inspired by the children’s book “Make Way for Ducklings,” dressing as characters and enjoying a festive atmosphere with various activities.
What is Glow in the Park?
Glow in the Park, held in June, features live music, light installations, interactive games, and food from local vendors, creating a lively event to kick off the summer in Boston.
Conclusion
Boston’s annual events showcase the city’s rich culture, community spirit, and history. From vibrant festivals like the Puerto Rican Festival to unique gatherings like Duckling Day, there’s something for everyone.
Explore the Boston Blooms Block Party for a taste of spring or join the excitement of the Boston Dragon Boat Festival in June.
Each event offers a distinct experience, enriching Boston’s lively atmosphere. So, whether you’re a local or a visitor, these top 10 annual events provide a fantastic way to immerse yourself in the heart of Boston.
Keep an eye on specific dates and plan your visit to enjoy the best the city has to offer. Don’t miss the iconic Boston Marathon in April, which attracts runners and spectators from around the globe.
The Head of the Charles Regatta in October is another must-see, providing thrilling rowing races along the Charles River.
Laura Chassaigne