May in Boston, Massachusetts, is a month packed with live concerts, theater performances, sports events, and cultural shows. From major league baseball games at Fenway Park to world-class concerts at TD Garden and performances at iconic theaters, Boston offers something for every taste.
This guide covers all the top Boston events in May 2026, helping locals and visitors plan their schedules, find the best tickets, and enjoy the city’s vibrant entertainment scene. Whether you’re a music lover, theater fan, sports enthusiast, or just looking for something fun to do, this guide has you covered.
Houston Astros at Boston Red Sox – May 3, 1:35 PM, Fenway Park
Baseball fans won’t want to miss the Houston Astros visiting the Boston Red Sox at the legendary Fenway Park. This game promises intense action, a festive atmosphere, and the perfect spring day for sports lovers. Make sure to secure your tickets early, as home opener games and high-profile matchups often sell out quickly.
Philadelphia Union at New England Revolution – May 9, 7:30 PM, Gillette Stadium
Soccer enthusiasts can catch the MLS matchup between Philadelphia Union and New England Revolution at Gillette Stadium. Enjoy a thrilling match in a modern venue with excellent seating and fan amenities.
Top Concerts in Boston – May 2026
Boston hosts a variety of live music performances in May, ranging from classical to pop, rock, and Latin music:
Luka Sulic: Life Tour – May 5, 7:30 PM, Emerson Colonial Theatre
Experience the incredible cello talent of Luka Sulic as he tours for his Life Tour. This intimate performance combines classical mastery with modern musical arrangements for an unforgettable evening.
The Hold Steady – May 2, 8:00 PM, The Sinclair
Fans of indie rock can enjoy The Hold Steady at The Sinclair, one of Boston’s premier music venues. Known for its vibrant atmosphere and excellent acoustics, The Sinclair is perfect for an energetic live show.
Carlos Vives – May 10, 7:00 PM, Agganis Arena
Latin music superstar Carlos Vives brings his hits and infectious rhythms to Boston at Agganis Arena. Expect a high-energy performance filled with dancing and celebration.
Hatsune Miku – May 10, 8:00 PM, Boch Center Wang Theatre
Experience the groundbreaking virtual pop star Hatsune Miku live. The performance combines holographic visuals, electronic music, and interactive fan experiences.
Jon Batiste – May 13, 7:30 PM, Boston Symphony Hall
Jazz and soul fans will love Jon Batiste at Boston Symphony Hall, offering an evening of vibrant music and memorable performances in one of the city’s most prestigious venues.
Khalid – May 29, 7:30 PM, MGM Music Hall at Fenway Park
R&B sensation Khalid brings his soulful hits to Boston, performing at the MGM Music Hall at Fenway Park. Expect a night full of energy, fan favorites, and new material.
Don Toliver – May 30, 7:30 PM, TD Garden
Hip-hop fans can catch Don Toliver at TD Garden, performing his chart-topping songs in one of Boston’s largest indoor venues.
Comedy Shows – May 2026
Boston’s comedy scene is thriving with top comedians performing live:
Shane Gillis – May 7, 8:00 PM, TD Garden
Enjoy a night of laughter with Shane Gillis, whose witty observations and high-energy delivery make for an unforgettable evening.
Alex Edelman – May 30, 7:00 PM, Emerson Colonial Theatre
Comedy fans can see Alex Edelman perform live at Emerson Colonial Theatre, offering sharp humor and hilarious storytelling.
Zarna Garg: Million Dollar Excuses – May 16, 7:00 PM, Chevalier Theater
Zarna Garg delivers a unique stand-up performance combining cultural commentary and personal anecdotes that resonate with audiences of all backgrounds.
Theater & Dance Performances – May 2026
Beauty and the Beast – May 2, 2:00 PM & 8:00 PM, Boston Opera House
Families and theater enthusiasts can enjoy Disney’s Beauty and the Beast at Boston Opera House, offering a magical musical experience with stunning costumes and timeless songs.
Alvin Ailey American Dance Theater – May 2, 2:00 PM, Boch Center Wang Theatre
Experience world-class contemporary dance with Alvin Ailey American Dance Theater, known for its dynamic performances and breathtaking choreography.
Ashley Kutcher – April 25, 8:00 PM, The Sinclair
While technically in late April, this show offers a crossover experience for those planning into May. Enjoy a modern theatrical performance blending music and storytelling.
Calum Scott – April 25, 8:00 PM, Orpheum Theatre Boston
Another late April performance that leads into May events, Calum Scott brings emotional ballads and incredible vocal performances in a historic venue.
Tips for Attending Boston Events in May 2026
Ticketing: Book early to secure the best seating. Popular shows like Don Toliver and Carlos Vives can sell out fast. Consider VIP packages for exclusive experiences.
Transportation: Boston’s MBTA subway and bus system offer convenient access to venues. Fenway Park and TD Garden are easily reachable by public transit.
Parking: If driving, reserve spots near venues in advance. TD Garden, Fenway Park, and Agganis Arena have limited on-site parking.
Dining & Entertainment: Plan pre- or post-show meals at nearby restaurants. Boston’s theater district and downtown areas are filled with dining options.
Accommodation: May is a busy month in Boston. Book hotels early near TD Garden, Fenway Park, or the theater district for convenience.
Family-Friendly Events
Boston in May has plenty for families:
Beauty and the Beast at Boston Opera House
Alvin Ailey American Dance Theater
Hatsune Miku performance for older kids and teens
Boston sports events like the Red Sox games at Fenway Park
Families can combine entertainment with Boston sightseeing, including the Freedom Trail, Boston Common, and the Public Garden.
FAQ – Boston Events May 2026
Q: How can I buy tickets for Boston events in May 2026? A: Purchase online through official vendors. Venues offer general admission, reserved seating, and VIP packages. Early booking ensures the best seats.
Q: What are the top venues for music and theater in Boston in May? A: TD Garden, Fenway Park, Boston Symphony Hall, Boston Opera House, Boch Center Wang Theatre, and Emerson Colonial Theatre.
Q: Are there family-friendly events in May? A: Yes. Shows like Beauty and the Beast and Alvin Ailey Dance Theater are perfect for families. Sports games at Fenway Park also make for fun outings.
Q: What should I know about parking and public transportation? A: Boston has great public transit. MBTA subway and buses are convenient. If driving, reserve parking near TD Garden, Fenway Park, or Agganis Arena.
Q: Can I attend multiple events in one day? A: Yes, but check start times. Some concerts, theater shows, and sports events may overlap. Plan your schedule to maximize your experience.
Explore More Boston Concerts & Venues
Looking for more live music events in Boston? Fenway Park is just one of the city’s premier venues hosting top concerts all year round. Discover upcoming shows, ticket options, and venue details to plan your perfect night out.
Check out all Boston concert venues to find your favorite artists and live music events across the city.
Explore Fenway Park events to see upcoming concerts, ticket availability, and exclusive VIP packages at this iconic venue.
Whether you’re searching for country, rock, pop, or jazz, Boston has a vibrant music scene, and you can find tickets for every concert, including Zac Brown Band and other top artists, right here.
Boston in May 2026 offers a dynamic calendar of concerts, comedy shows, theater, dance, and sports events. Whether you’re cheering at a Red Sox game, enjoying Carlos Vives live, or experiencing Alvin Ailey’s breathtaking dance, the city has something for everyone. Plan ahead, secure your tickets, and enjoy Boston’s vibrant entertainment scene this May.