Take a look at the Boston Event Calendar for May to discover exciting ways to enjoy the spring season. As the city comes alive with blossoms and sunshine, it’s the perfect time to get outside and explore.

Highlights this month include the three-day Boston Calling Festival, the kickoff of whale watching cruises, art walks, Mother’s Day celebrations, Memorial Day Weekend happenings, and a variety of concerts!

 

 

Other major May highlights include Lilac Sunday, the Garden of Flags display on Boston Common, the whimsical Duckling Day Parade, scenic Harbor cruises, the Hidden Gardens tour of Beacon Hill, and a full lineup of shows in the Theatre District.

Make the most of the warm spring weather with a Boston Duck Tour, catch a Red Sox game at iconic Fenway Park, join a Historic Pub Crawl along the Freedom Trail for a unique way to see the city, or simply unwind with some outdoor patio dining at one of Boston’s fantastic restaurants.

 

 

Boston Calling 2025

 

The Boston Calling Music Festival, a beloved three-day celebration of indie, pop, country, and rock, returns to the Harvard Athletic Complex in Allston over Memorial Day Weekend—bigger and better than ever.

This year’s headliners include Luke Combs, Sheryl Crow, Megan Moroney, and T-Pain on May 23; Fall Out Boy, Avril Lavigne, and The Black Crowes on May 24; and Dave Matthews Band and Vampire Weekend on May 25.

The stacked lineup also features standout performances from Sublime, Kyle Dion, TLC, Public Enemy, Spin Doctors, Sam Austins, Sofia Isella, Battlemode, and many more.

Get ready for an action-packed weekend with three music stages, a dedicated comedy stage, and performances from over 50 artists—more music than ever before! You’ll also find 30+ food vendors, a diverse selection of beer and wine, sponsor exhibits, and plenty of surprise attractions throughout the festival grounds.

Tickets tend to sell quickly and prices increase as the event approaches. In addition to single-day passes, you’ll find 3-day passes and a tiered range of VIP ticket options—the higher tiers usually sell out first, so it’s smart to grab yours early.

 

 

Whale Watching Season Begins!

Boston’s whale watching cruises are set to begin on May 15 (date to be confirmed), starting a bit later than usual this year. That means the season will be shorter—so if you’re planning to go, don’t wait to book your tickets!

These thrilling 3.5 to 4-hour trips take you through Boston Harbor and out to Stellwagen Bank, a federally protected marine sanctuary located about 25 miles offshore.

Expert marine biologists or naturalists are on board to guide the experience and help you spot incredible sea life.

What might you see? On a typical outing, you could encounter a variety of large whales, dolphins, seabirds, and other fascinating marine animals.

And don’t forget your camera—you’ll want to capture every breathtaking moment!

 

 

Boston Concerts & Shows

Top concerts in Boston in May 2025 include AC/DC, Shakira, Warren Zeiders, the 3-day Boston Calling Music Festival over Memorial Day Weekend, Jason Aldean, and Candlelight Concerts – plus more:

• Warren Zeiders – MGM Music Hall – May 3
• AC/DC – Gillette Stadium – May 4
• Kendrick Lamar & SZA – Gillette Stadium – May 12
• Boston Calling Music Festival – 3-Day Pass – 3-day pass- Harvard Athletic Field – May 23 – 25
• Boston Calling May 23 tickets – Luke Combs, Sheryl Crow, Megan Moroney, and T-Pain
• Boston Calling May 24 tickets – Fall Out Boy, Avril Lavigne, Cage the Elephant, The Black Crows
• Boston Calling May 25 tickets – Dave Matthews Band, Vampire Weekend, Sublime, Public Enemy
• Shakira – Fenway Park – May 29
• Jason Aldean & Brooks and Dunn – Fenway Park- May 30
• Pierce The Veil, Sleeping with Sirens – Xfinity Center – May 30
• Post Malone & Jelly Roll – Gillette Stadium – May 31
• Candlelight Concerts – Multiple dates in May at various locations

 

 

Memorial Day Weekend Events in Boston 2025

When: Monday, May 26 – Memorial Day 2025

While many locals head to the Cape or the mountains for the long weekend, visitors to Boston get the best of both worlds—plenty of exciting events to enjoy, lighter crowds, and potentially easier access to tickets and reservations.

Memorial Day Weekend in Boston offers a wide range of activities. Pay tribute during moving remembrance ceremonies, including the iconic Garden of Flags on Boston Common, or soak up the start of summer with festive options like the Boston Calling Music Festival (don’t wait to grab your tickets!), scenic waterfront attractions, and a classic Red Sox series at Fenway Park as they take on the Brewers on May 23, 24, and 25.

 

 

Boston Harbor Sightseeing Cruises

Explore the city from the water with these unforgettable Boston Harbor cruises aboard the Yacht Northern Lights and Schooner Adirondack III & IV. Whether you’re in the mood for sightseeing, a relaxing sunset sail, or live entertainment, there’s something for everyone.

 

Popular Cruises

• Northern Lights Sunset Cruise – Sip a drink from the onboard bar and relax as you cruise through the harbor. Catch the magical moment the USS Constitution fires its evening cannon just as the sun dips below the horizon.
• Northern Lights Brunch Cruise – Indulge in a delicious three-course brunch while enjoying a scenic ride around Boston Harbor—perfect for a weekend treat!
• Northern Lights Sightseeing Cruise – Soak in Boston’s iconic landmarks and rich history on this comfy harbor cruise. A great outing for friends and family. Food and drinks available for purchase onboard.

 

Sailing Cruises on the Adirondack III & IV (Starting May 1)

• Adirondack Day Sail – Feel the breeze and sunshine as you glide through Boston Harbor and past the Inner Harbor Islands on this laid-back afternoon sail.
• Adirondack Sunset Sail – Unwind with a peaceful evening cruise as the sky lights up with sunset hues over the water.

 

Special Cruise: Mother’s Day

• Mother’s Day Brunch Cruise with Live Jazz – Treat Mom to a relaxing cruise on May 11, complete with a gourmet brunch and live jazz. This one sells out every year—book early!

 

Plan Ahead: July 4th Cruises (Book early—they fill fast!)

July 2

• Northern Lights – Harborfest Fireworks Cruise (1920s-style yacht)
• Adirondack – Harborfest Fireworks Cruise (80-foot schooner)

July 4

• Adirondack – USS Constitution Turnaround Cruise with Continental Breakfast
• Northern Lights – USS Constitution Turnaround Cruise with 3-Course Brunch
• Northern Lights – July 4th Fireworks Cruise (3 hours, Winthrop Fireworks)
• Adirondack – July 4th Fireworks Cruise (3 to 3.5 hours, Winthrop Fireworks)

 

Labor Day Weekend

• Northern Lights Labor Day Fireworks Cruise – Avoid the crowds and enjoy the spectacular fireworks over Boston Harbor from the comfort of this classic commuter yacht—an unforgettable way to close out summer.