Live music in Nantucket, MA

An outdoor celebration at Christ the King Parish brings Italian food, drinks, and music to Mashpee, transforming the town into Little Italy for a single festive evening. The gathering features a five-course Italian feast for 400 guests catered by Pink Door Catering, paired with live performances. Italian tenor Aaron Caruso serenades diners, and young performers from Steeple Street Music Academy share the stage. All proceeds support the Mashpee Chamber Scholarship Fund and the #ShopMashpee campaigns.

Enjoy live Irish music at an open session hosted by Rose Clancy and her band of musicians, with dinner, drinks, and plenty of sing along fun.

Summer Concert Night at the Bandstand features a live set from Entrain at the Mashpee Commons Bandstand. The eclectic six piece from Martha’s Vineyard has been performing and recording since its first show in March 1993, celebrating more than three decades together. The concert is free and open to the public, and attendees are encouraged to bring a lawn chair or blanket. Naukabout Beer Garden will offer snacks and brews, and Smith Family Popcorn will provide complimentary lightly salted popcorn with additional flavors available for purchase. Outside alcoholic beverages are not permitted at Bandstand shows. If weather becomes a concern, the event will move indoors and day-of updates will be shared on social media.

The first Friday of the month features a singing-focused gathering hosted by Stephanie Viva. This monthly party is all about music and a great time.

Freebird Patio Sessions is a new live music residency at Freebird Motor Lodge presented by Cape Symphony Presents as part of the Summer Sessions on 28 series. Shaped by the lodge’s retro, rock and roll spirit, the programming offers carefully curated performances that bring together locals, travelers, artists, and the wider Cape Cod creative community. All shows are free, creating an easygoing setting for poolside relaxation, cocktails, outdoor social time, and discovery at a distinctive boutique destination. Drawing on vintage Americana style and an independent edge, the series blends singer-songwriters, indie acts, DJs, soul-leaning performers, and eclectic regional talent into a focused yet laid-back listening experience. Developed in collaboration with Reverie Brands and aligned with sister efforts like The Uncommoner Hotel and Gypsy Sol Sessions, it champions destination-driven arts programming that strengthens connections between visitors and residents across the Cape.

A relaxed party on the beach with an easygoing, friendly vibe.

Lakeside at Naukabout on Cape Cod, the 2026 Saturday Sunset Series features Red Neck Castaway celebrating the songs of Kenny Chesney. This outdoor summer concert pairs tribute performances with a relaxed waterfront setting, craft beverages, and plenty of food. The show goes on in any weather and is open to all ages. Children who are ready to dance will need their own ticket, and dogs are not permitted during concerts. Look for a range of refreshments such as craft beer, cocktails, mocktails, burgers, pizza, salads, and more, and settle in by the lake for live music.

Elvis Costello takes the stage at the Old Whaling Church in Martha's Vineyard for a special benefit concert, presenting his blend of rock, new wave, and singer songwriter storytelling in an intimate setting. The evening includes an opening performance by Will Dailey.

A lively singalong with a dueling pianos show invites crowd song requests, paired with an evening of dinner and drinks. Expect high-energy piano back-and-forth and plenty of audience participation. There is no cover charge.

Enjoy a country-themed brunch with mimosas, breakfast sandwiches, bloody marys, and tatter kegs, with the complete food and drink menu available. Live country music from Carly Tefft, Rick Lockwood, and other artists sets an upbeat tone for a relaxed meal.

Set along the lake at Naukabout, Never Miss A Sunday Show is a weekly outdoor concert series showcasing nationally touring artists alongside regional favorites in roots rock, funk, and Americana. This edition features Kung Fu and requires tickets. Enjoy live music in a relaxed setting with craft beer, cocktails, mocktails, and a menu that includes burgers, pizza, salads, and more. The series takes place rain or shine and welcomes all ages. For ticketed performances, children who are ready to dance need their own ticket. Dogs are not permitted during concerts, and the atmosphere centers on community and great summer music on Cape Cod.

The George Gritzbach Band delivers an evening of original roots and blues that moves from tender, soulful ballads to high energy, rhythm-driven tunes. Expect story-centered writing grounded in the blues tradition, highlighted by notable slide guitar that keeps the sound unvarnished, vibrant, and full of life. The Washington Post has recognized George Gritzbach for standout songwriting and memorable slide work, and his résumé includes opening slots for B.B. King, Bonnie Raitt, and Dr. John, plus appearances at The Melody Tent, The Music Circus, Cotuit Center for the Arts, The Music Room, and festivals across the United States and Canada. Drawing on influences like Rev. Gary Davis, Robert Johnson, B.B. King, and Elmore James, this performance channels classic blues spirit through fresh original songs from a veteran touring artist. Tickets are $30, with a $25 member rate.

Presented by the Yarmouth Chamber of Commerce, the Yarmouth Summer Concert Series turns Parker's River Beach into a lively seaside stage with free, family friendly music. This date features SummerTown, a Cape Cod band blending classic rock, Americana, and contemporary favorites for an energetic set that encourages singing along and dancing in the sand. Attendees can bring a blanket or beach chair, settle in by the water, and enjoy the ocean breeze, upbeat tunes, and a welcoming community vibe. The series is supported by Cape & Coast Bank, The Steamship Authority, Skipper Chowder House, Signarama, Cape Cod 5, and Cape Cod Gourmet.

Pitchfork presents a free concert at Brooks Park Harwich as part of a concert series.

Donavon Frankenreiter, with Iris And The Shade, is performing at The Chicken Box. The show starts at 8:00 PM.

Part of the 2026 Summer Concert Series at Mashpee Community Park, this performance spotlights Bourbon Sunset Trio. The weekly series brings live music on Tuesdays and showcases a rotating lineup that also includes Paradise Rock, Kim Moberg and Heather Swanson, Jody Moore Band, Monica Rizzio and the Round Up Band, Hotstreak, Heyday, and Cape Coda.

A no-cost concert for families presented by the Cape Cod Chamber Music Festival takes place at the First Congregational Church of Chatham. Festival Artistic Director Jon Manasse on clarinet leads the program with his son, Jordan, at the piano, and his new daughter-in-law, violist Alyssa Yuge. The music is tailored for children ages four to eight, while all ages are welcome. No tickets are required and casual clothing is encouraged, offering an easy way for young listeners to explore chamber music.

Renée Levesque takes the stage at the Mashpee Commons Bandstand as part of the MVYRADIO Summer Concert Series, a season of free, live performances. Enjoy snacks and beer from Naukabout Beer Garden, plus complimentary lightly salted popcorn from Smith Family Popcorn, with additional flavors available to purchase. Outside alcoholic beverages are not allowed at Bandstand shows. If weather intervenes, the concert will move indoors and day-of updates will be shared on social media.

Enjoy a weekly summer Music Bingo session that puts music knowledge to the test. An MC hosts rounds built around a mix of sounds, from today’s hits to classic rock, hair metal, hip hop, pop, and more, turning each card into a fun guessing game. No registration is needed, though spots can fill quickly.

Grace Kelly returns to the Cape Cod Jazz Festival at Wequassett, known worldwide as a saxophonist, singer, and composer. A fixture on this stage since she was 18, she brings her “Gracified” sound, a seamless blend of high-level jazz, soulful vocals, and vibrant, cross-genre energy. With 15-plus albums and over 1,500 shows across the globe, she connects with fans of jazz, funk, and pop. Expect a dynamic performance that pairs technical brilliance with inviting stage presence, a seasonal standout on Pleasant Bay. Jazz Dinner reservations are available, and the performance is free and open to the public.

RIPÉ brings rock and punk energy to The Chicken Box in Nantucket. The show starts at 9:00 PM, with tickets available through Spotify’s ticket partners.

The Faux Paws craft a sound that slips past easy labels. Instead of settling into a single genre, they pull from bluegrass, old time, Celtic influences, folk, Americana, jazz, and singer songwriter traditions, blending those threads to fit each musical idea. The energy is bold, heartfelt, cheeky, and full of left turns, all anchored by a steady groove that keeps everything alive. On stage, expect dazzling playing on fiddle, mandolin, guitar, and saxophone alongside personal lyrics, tight three part brother harmonies, lively onstage chemistry, carefully shaped arrangements, and improvisations that take flight. Building on momentum in recent years, the group expanded to include a fourth “Paw” on upright bass, most often Felix Sartori, adding depth to the sound and giving every member more room to explore. Listeners in the acoustic world have embraced the band’s one of a kind approach, and a live set moves through shifting moods and influences while keeping the pulse front and center.