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21 Annual Events In Boston To Mark Your Calendars

Of course, there are significant annual events that all Bostonians (and newbies) know, like the Boston Marathon, The Pops on the 4th of July, and great yearly events happening all over Boston, including Cambridge, Brookline, and Somerville.

Whether planning a trip to Boston or having lived here for decades, these are some of the best annual events to explore the city’s culture, have fun, and meet community members.

1. Boston Blooms Block Party

Happens In: April

With its annual event launching last year, the Boston Blooms Block Party is a springtime block party that welcomes employees, residents, and visitors to Downtown Boston. This festival is an all-day event consisting of food trucks, live music, art installations, a pop-up beer garden, and more. It’s a great springtime festival you won’t want to miss!

Scheduled For: TBD

2. Brookline Springfest

Happens In: May

The Brookline Spring Festival celebrates trees, including a kickoff of the Town’s recently completed Urban Forest Climate Resiliency Master Plan and an Arbor Day planting and proclamation. This community gathering includes fun family-friendly activities, including yard games, crafting stations, a scavenger hunt, food, and live music.

Scheduled For: TBD

3. Wake Up The Earth Festival

Happens In: May

The “Wake Up The Earth” Festival served as a long-standing annual event that is a celebration of community, diversity and activism. Held in Jamaica Plain, the festival occurs after the parade, taking place at the Southwest Corridor, next to the Stony Brook T. The festival aims to promote community engagement and activism, and often features local artists and performers.

Scheduled For: May 6th, 2023

4. Let’s Dance Boston! Rose Kennedy Greenway

Happens In: May

Let’s Dance Boston, one of the largest free outdoor dance and music parties in Boston. It is open to people of all ages and skill levels. 

Located at the Rose Kennedy Greenway, the Let’s Dance Boston features five consecutive nights of electrifying music and dance during weekday evenings. Each day of the festival features a different dance style, such as salsa, swing, and ballroom. You get free lessons, open dancing, live music, and food trucks on site. This is a great opportunity for people to come together, welcome the warmer weather in Boston, and enjoy dancing in a beautiful outdoor setting.

5. Lilac Festival Arnold Arboretum

Happens In: May

The Lilac Festival held at Arnold Arboretum is a beloved tradition in Boston that celebrates the blooming lilacs in the springtime. The event typically takes the second Sunday in May and features a variety of activities such as guided tours of the lilac collection, food and crafts vendors, and children’s activities. The Lilac Festival is a great opportunity to enjoy the beauty of the lilacs and natural surroundings with friends and family. The Lilac Festival is the only day the Arboretum “officially” allows Picnicking.

Scheduled For: May 14, 2023

6. Glow in the Park Rose Kennedy Greenway

Happens In: June

The Glow in the Park festival lights up the Rose Kennedy Greenway every June and is a great way to kick off summer in Boston. The event features awesome live music, light installations, lawn games, Boston’s best food and drink vendors. And, of course, no Glow in the Park event would be complete without glow sticks and glowing hair and make-up by Glamsquad. Be sure to buy a ticket and dance the night away to live music, with donations going to the Greenway Conservancy.

Scheduled For: June 9, 2023

7. Save The Harbor Beach Bash – Constitution Beach, Piers Park

Happens In: July

eastietimes.com

Eastie Week is a celebration of the rich, vibrant, and resilient community of East Boston – its people, history, culture, music, and art. This week-long neighborhood festival has a packed schedule of FREE and low-cost, family-friendly activities hosted by East Boston organizations and partners.

The best family-friendly event of Eastie Week is the annual Save the Harbor Beach bash at Constitution Beach in East Boston. This event features live music, food and drinks, family-friendly entertainment, and beach activities like crabbing, fishing, and swimming. The event serves as a fundraiser for the organization and aims to raise awareness about the importance of protecting and preserving the environment of Boston Harbor.

Scheduled For: TBD

8. Puerto Rican Festival – Franklin Park

Happens In: July

The Puerto Rican Festival is an annual event that takes place in Franklin Park, in Boston. The festival is organized by the Franklin Park Coalition, and celebrates the Puerto Rican culture and community. The festival features live music and dance performances, delicious food, arts and crafts vendors, and many activities for children. It is also features one of Boston’s largest parades, including marching twirlers, colorful dance troupes, bands, and musical floats. Spend the day learning and celebrating Puerto Rican culture and enjoy the music, food, and activities.

Scheduled For: July 28th-30th, 2023

9. Charles River Jazz Fest – Herter Park

Happens In: July

A new event founded in 2021, The Charles River Jazz Festival is an all-day music and art experience located on the banks of the Charles River at Herter Park in Allston. The event showcases the many sides of Jazz music in the Boston area. Attendees can watch phenomenal performances at the Herter Park Amphitheater to support local musicians and artists who embody the heart and soul of jazz. 

Scheduled For: TBD

10. Cambridge Jazz Festival @ Danehy Park

Happens In: July

Cambridge Jazz Festival is an annual festival held at Danehy Park, that is free and open to the public rain or shine. The festival features exciting performances from world-class jazz artists. There will be food trucks, a kids area, a jazz museum and more. Don’t forget to bring a lawn chair or comfortable blanket!

Scheduled For: TBD

11. Shakespeare on the Common

Happens In: July and August

Enjoy a magical night watching Shakespeare under the stars on a summer evening on the Boston Common. Commonwealth Shakespeare Company’s “Free Shakespeare On The Common” is one of Greater Boston’s most beloved traditions and magical events. A new Shakespeare play is performed each year, taking place several nights in late July and early August. The plays are performed on a stage near the Parkman Bandstand on the Boston Common. Make sure you bring a blanket or comfortable folding chair to sit on. While this is a free event, donations are encouraged. 

Scheduled For: TBD

12. Boston Greenfest – Rose Kennedy Greenway

Happens In: August

Boston Greenfest is an annual event that focuses on environmental sustainability and features various activities related to conservation, green living, innovation, and renewable energy. The event takes place at Rose Kennedy Greenway, and typically includes educational exhibits, workshops, live music, and food trucks. This unique festival is an opportunity for people to learn more about environmental sustainability while experiencing the Rose Kennedy Greenway in a new way.

Scheduled For: TBD

13. Art in the Park @ City Square Park

Happens In: September

Art in the Park is an annual event that takes place at the historic City Square Park in Charlestown, steps away form the Freedom Trail. The event features artists and artisans displaying and selling their work, including paintings, drawings, photography, sculpture art, jewelry, and handmade crafts. The event is typically held in the summer and is a great opportunity for people to discover new artists and purchase original artwork. The event is sponsored by local businesses and the Artists Group of Charlestown (AGC), a volunteer-driven organization.

Scheduled For: TBD

14. Boston Arts Festival @ Christopher Columbus Park

Happens In: September

The Boston Arts Festival takes place on the second weekend in September in the afternoon at Christopher Columbus Waterfront Park. This festival is designed to showcase the visual and performing arts in Boston. Each year thousands of attendees come to see local visual artists, craftspeople, local musicians. Vendors sell a wide variety of high-end art and craftwork, including painting, photography, ceramics, jewelry sculptures, and more. There’s no better way to to experience the city’s vibrant arts scene!

Scheduled For: TBD

15. FensFest at Fenway Victory Gardens

Happens In: September

FensFest is an annual event that takes place at the Fenway Victory Gardens in Boston’s Fenway neighborhood.

Hosted by Fenway Garden Society, this neighborhood event is free and open to the public. The afternoon is full of food and desserts, welcoming guests to bring side dishes and desserts to share. There are lawn games and games for kids, including a pinata and a raffle drawing. Fenway neighbors for a fun afternoon in the park and great live music. The event is held in the summer and is a great opportunity for people to enjoy the beauty of the Fenway Victory Gardens, and learn more about gardening!

Scheduled For: TBD

16. Riverfest @ Baxter Park

Happens In: September

Riverfest is a festival that takes place in Somerville’s Assembly Row at Baxter Park, located along the banks of the Mystic River. This annual event includes live, local music performances, family-friendly activities, and spectacular fireworks over The Mystic River. Come for family-friendly events like chalk art, face painting, stilt walkers, and an artisan market. Hours of live music during the afternoon, leading into the fireworks over the Mystic at night to end the event.

Scheduled For: TBD

17. Lantern Parade @ Jamaica Pond

Happens In: October

A longstanding ritual in the Jamaica Plain neighborhood is the Jamaica Pond Lantern Parade, a festive family-friendly Halloween annual tradition. Community members host lantern-making workshops where attendees create beautiful handmade lanterns that can either be carried during the parade, or hung up. The lanterns are made from recycled soda bottles and decorated with colorful tissue paper. Children and adults dress up in Halloween costumes for the parade around the pond.

Scheduled For: TBD

18. Food Truck Festival Rose Kennedy Greenway

Happens In: October & May

The Greenway Food Truck Festival is an event that takes place at the Rose Kennedy Greenway, and features Boston’s best food trucks. The festival features a variety of food trucks from local vendors, offering a diverse range of cuisines and dishes. This annual event is a great opportunity for people to enjoy delicious, mouth-watering food, while also experiencing the beauty of the Greenway.

Scheduled For: TBD

19. Holiday Trellis Lighting @ Christopher Columbus Park

Happens In: November

The 260-foot Trellis at Christopher Columbus is one of Boston’s most romantic spots, especially during the holiday season. The Friends of Christopher Columbus Park hosts the holiday trellis lighting at Christopher Columbus Park every year. The trellis is decorated with holiday lights and decorations, creating a festive and colorful display. The annual lighting often includes cookies, hot chocolate and and other holiday treats. Kids may even get an early visit from Santa Claus.

Scheduled For: TBD

20. Tree Lighting @ Boston Common

Happens In: December

The Tree Lighting at Boston Common marking the beginning of the holiday season in Boston. Every year, a large Christmas Tree is given to the people of Boston by the people of Nova Scotia, and place in the center of the park. This joyous ceremony draws a large crowd that features entertainment, appearances by Santa, fun activities for kids, and perhaps refreshments. Be ready to sing traditional holiday songs to celebrate the season.

Scheduled For: TBD

21. Waterfront Ice Sculptures

Happens In: December

Waterfront Ice Sculptures is an annual event that takes place along the Boston waterfront. The event features creatively designed ice sculptures created by professional ice sculptors, which are illuminated at night to create a magical display. Last year, thirty ice sculptures were displayed at sites like South Boston Maritime Park, Martin’s Park, Rose Kennedy Greenway, Christopher Columbus Park and Piers Park. The Waterfront Ice Sculptures are a wonderful way to spend new years eve while enjoying the beautiful Waterfront District.

Find Festivals in Boston Using Urbnparks

There’s so much going on in the city! As the weather gets warmer, you can use Urbnparks to find festivals and neighborhood gatherings of all types. Get started exploring festivals and gatherings here.

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