Things to Do North of Boston this May

Things to Do North of Boston this May

May 1, 2024

May means all of the things we love the most. Our flowers are blooming, our birds are chirping and our outdoor patios, farms, and seasonal businesses are welcoming visitors for a whole new season! Our local charters, cruises, and whale watches return to the waters and passengers are jumping aboard to experience the beauty of the North Shore from sea. Mother’s Day is just two short weeks away and Memorial Day is right around the corner too! Before long summer will be in full swing and we just want it to slow down a bit so we can savor it all! Excitement awaits you everywhere North of Boston this month. May you get out and enjoy it!


Through May 19: UP AND COMING, Young Artists with Promise, Rocky Neck Art Colony

Now on display at the Cultural Center at Rocky Neck is an exhibit by many talented local artists. Browse the works Friday through Sunday from noon to 5 pm through May 19th.


May 3–5: Comedian Bob Marley, Blue Ocean Music Hall

Celebrating 15 years as a stand up comic, Bob Marley is one of the hottest and most sought-after comedians in the country. He has been featured in his own special on Comedy Central, and is one of the few comics to do the complete late night television circuit, Late Show with David Letterman, The Tonight Show with Jay Leno, Late Night with Conan O’Brien, The Late Late Show with Craig Ferguson, and The Late Late Show with Craig Kilborn.


May 3: Back to the 80’s Prom Fundraiser, Lynn Museum

Grab your dyed satin heels, cummerbund with matching bow tie, and join Lynn Museum/Lynn Arts for their Back to the 80s Prom! The evening will begin at 5:30 pm with a reception at the Museum featuring live music by The Dudes, elevated appetizers by Every Little Breeze Catering, a cash bar, and a unique opportunity to view prom-related objects from the Lynn Museum collection. At 7 pm, go back to the 80s at The Vault in LynnArts and party in true 80s fashion with DJ Dana, cash bar, snacks, and punch.



May 4–5 & May 11–12: Tulip Fest, Cider Hill Farm

A gorgeous, fan-favorite variety of 100k tulips are scheduled to bloom in early May. Welcome spring with this multi-weekend festival featuring free live music, self-guided blooming orchard walks, outdoor hard cider bars, food trucks, fitness n’ family activities and pick-your-tulips. General entrance is free but online tickets for tulip picking is required. Walk-in tickets will not be sold upon arrival on the farm.


May 4 & 5: Cape Ann Blossoms in the Galleries

Join Cape Ann Museum for a weekend of creativity, where artistic masterpieces are brought to life through the eyes of talented floral artists. Floral viewing enjoyment is included with General Admission or free for Cape Ann Museum Members on Saturday, May 4, and Sunday, May 5 from 10 am to 5 pm.


May 6, 13, 20 & 28: A Series on Art & Community Through the Ages, Hammond Castle Museum

Step into a world of creativity and exploration with Hammond’s thought-provoking series: Image, Invention, and Imagination: A Series on Art & Community Through the Ages. Join them on a captivating journey through history as we explore the profound connections between art, innovation, and the human imagination.


May 7–19: Jersey Boys, North Shore Music Theatre

They were just four guys from Jersey, until they sang their very first note. They had a sound nobody had ever heard … and the radio just couldn’t get enough of. But while their harmonies were perfect on stage, off stage it was a very different story – a story that has made them an international sensation all over again.






May 9: Margaret Glaspy: Unplugged, Rockport Music

For the first time, indie singer/songwriter Margaret Glaspy is presenting a solo acoustic show filled with songs from her past and present. Freshly off the heels of her third full-length album, Echo The Diamond, the music emerged from a deliberate stripping-away of artifice to reveal life for all its harsh truths and ineffable beauty. With Opening Act: Ryan Lerman (of Scary Pockets).



May 10–27: The Net Works, Maritime Gloucester

The Net Works is a multi-sensory installation built upon the narrative of Gloucester’s fishing community. The net serves as a literal and metaphorical symbol in an immersive exhibit that includes scents, sounds, and tactile experiences, where visitors, like fish, move through a passage of netting. It evolved during the pandemic and artist Erika Senft Miller’s consequent virtual residency with the Manship Artists Residency in 2020.



May 10 & 11: Deadwick’s Ethereal Faire, Castle Hill

A brand new experience awaits you at Deadwick’s Ethereal Faire, as the casino complex at Castle Hill becomes a magical market featuring over 50 vendors of arts and crafts to fascinate and transform you; food by Portsmouth’s Fezziwig to fill you; tarot readers, costumed characters, face painting, antique tin-type photography, and more to make your visit unforgettable. And if that’s not enough, there will also be shows (for an additional fee) featuring magicians, circus performers and more!


May 11: Spring Celebration, Marblehead

Discover Marblehead and the Marblehead Chamber of Commerce are teaming up with the Marblehead Arts Association, Marblehead Merchants, Marblehead Museum, local shops, restaurants, artists and organizations for the annual Marblehead Spring Celebration. This Collaboration is working to provide a festive showcase for local businesses, restaurants, makers and artists after what has been a tough year for everyone!


May 11: Big Night Out with Jay Leno, The Cabot

Join The Cabot for a fun night of music, comedy, and celebration in support of their biggest fundraiser of the year! You can keep the arts alive on the North Shore and ensure that our beautiful historic theater can continue to educate, inspire and entertain for generations to come. Join The Cabot along with acclaimed TV late night show host, admired stand-up comedian, best-selling children’s book author, much-in-demand corporate speaker, TV and movie voice-over artist, pioneering car builder and mechanic, and philanthropist…Jay Leno!

May 17: Grown-Ups Gala, Black Box Theater

Join the North Shore Children’s Museum for their first official Grown-Ups Gala on Friday, May 17th at the Black Box Theater in Peabody. This special evening is the signature fundraising event for our newly created 501c3, Friends of North Shore Children’s Museum, which provides critical funding for the museum’s income-based admission prices, educational exhibits, and robust and accessible program offerings.


May 18: Motif No. 1 Day, Rockport

The Greater Cape Ann Chamber of Commerce is excited to bring back this beloved community event, long cherished by residents and visitors as a celebration of Rockport’s iconic fishing shack. Join them on Saturday, May 18 (rain date May 19) for this all-day, family-friendly event including a 5K Road Race and Fun Run, EMS Day on T Wharf, vendors in Harvey Park, Cape Ann Plein Air, children’s activities, music, performing arts, gallery exhibitions, food trucks, and a beer tent.


May 18: Taylor Swift Brunch, Beauport Cruiselines

Calling all Swifties! What better way to celebrate the release of Taylor Swift’s new album, The Tortured Poets Department, than aboard Beauport Cruiselines? Gather your friends, enjoy a delicious brunch buffet, soak in the sweeping harbor views, sip on Taylor-themed cocktails, all while jamming out to Taylor’s hits with Live DJ Entertainment.


May 19: Pig Roast Luau, Tap Brewing

ALOHA! Join Tap Brewing in Haverhill on Sunday, May 19th for their Pig Roast Luau! Whole roasted hog and all the fixins, served picnic style on their back deck, and outdoor cash bar. Hipa hipa! Tickets available to purchase at their bar.






May 24: Friday Night Live ft. Back to the 80’s Band, Surf Side

The seacoast’s best live music dance party every Friday night on the beach is back! There’s no better place to see your favorite regional bands and rock the night away than on SurfSide’s giant oceanfront deck! Back to the 80’s plays the ultimate dance hits from artists such as Def Leppard, Journey, Michael Jackson, Heart, Whitesnake, Madonna, Poison & Pat Benatar!


May 31: The Last DJ with Cape Ann Pride, The Cut

Come out to a very special Last DJ and help Cape Ann Pride celebrate their first pride with a dance party and music by Coleslaw! No advance ticket purchase necessary. Dance your way into history at this kick-off to the first full #CapeAnnPride weekend! 21+ doors open at 8 pm, music at 8:30 pm.


Check out our event calendar for even more things to do North of Boston!