You can enjoy live outdoor music virtually every night of the week this summer. 

Shanties & Sails on Tuesdays in June 2026 from 5:30–6:30pm at Connecticut River Museum, Essex: Talented shanty and sea-song musicians perform free one-hour shows on the North Deck, with optional ticketed sailing aboard the historic vessel Onrust. Dates: 6/2, 6/9, 6/16, 6/23, 6/30.

Connecticut Early Music Festival on select weekends, 6/6–6/21 at various venues, New London area: An annual festival presenting European music written before 1800, featuring six concerts over three weekends in June.

Tunes on the Dunes on Mondays & Wednesdays, 6/6–8/12, 6–8pm at Westerly Old Town Beach, Westerly, RI: Monday Night Jams and Wednesday Blues on the Beach. 2026 lineup includes Sugar, Room Full of Blues Duke Robillard and more. 

Old Saybrook Summer Concert Series Old Saybrook Summer Concert Series, 6/10-8/21. Wednesdays at Harvey’s Beach starting at 6:30 and Fridays at Old Saybrook Town Green starting at 7pm. Family-friendly, bring a blanket and chairs.

Connecticut Sea Music Festival on 6/12–6/15 at multiple venues, Essex: A traditional maritime folk festival beginning with the Symposium on the Music of the Sea on Friday, followed by evening concerts and music throughout the town. Daytime events FREE; ticketed evening concerts.

Esker Point Beach Concert Series on Thursdays, 6/18–8/6 from 6–8pm at Esker Point Beach, Groton: Don’t miss Summer Sound Waves, eight weeks of community beach concerts presented by Groton Parks & Recreation. Family-friendly, alcohol-free. Food trucks on-site.

Make Music Day on 6/21/26 at various outdoor locations, Southeastern CT: Ring in the summer solstice with a worldwide day of free outdoor music celebrations at numerous locations. Anyone can perform; anyone can attend.

McCook’s Beach & Bandshell Concert Series McCook Point Park, Niantic on Wednesdays & Fridays from 6/19–8/28 from 6-8pm. Free concerts overlooking Niantic Bay, Wednesday evenings on the beach and Fridays in the bandshell. Bring lawn chairs, blankets, and a picnic. No alcohol permitted.

Branford Jazz on the Green on Thursdays, 6/25–8/20 at 6:30pm. Celebrating jazz since 2009, this weekly series presents world-class performers every Thursday behind Town Hall. 2026 lineup includes Rob Zinn, Greg Abate Quartet, Lindsey Webster, Phil Denny, and more.

Stonington Vineyards Summer Music Series on Fridays, 6/26–8/28 from 6–9pm: A seasonal tradition of music, food, and wine. Bring lawn chairs and blankets; picnic dinners welcome. Food trucks on-site. 20% of ticket proceeds benefit a local charity each week.

Watch Hill Sunset Concerts Watch Hill Village Green on select Tuesdays, 6/30–8/25 from 6–8pm. Free outdoor concerts on the Green on Bay Street every other Tuesday. 2026 dates: 6/30, 7/14, 7/21, 8/11, 8/25.

Grassy Strip Music Series on Thursdays from late June through the end of August at The Wharf at Madison Beach Hotel, Madison: Enjoy live outdoor shows on the iconic Grassy Strip overlooking the Long Island Sound. Food and beverages available for sale.

Chestnut Hill Concerts on Fridays, 8/7–8/28 at 7:30pm at The Kate, Old Saybrook: World-class chamber music on four consecutive Friday evenings in August, celebrating the series’ 57th season. Works by Mozart, Kodály, Schumann, Saint-Saëns, Debussy, Brahms, Schubert, Beethoven, and Prokofiev. Tickets on sale at The Kate’s Box Office.

Music on the River at the Goodspeed on Mondays, 7/13–8/17 from 6:30–8:30pm, East Haddam: A free concert series on the stunning lawn of the Goodspeed Opera House along the Connecticut River. Food and drink at the Gelston House or bring a picnic, lawn chair or blanket.

Guilford Craft Expo on 7/17–7/19 at Guilford Town Green, Guilford: Offered for over 60 years, this is one of the longest-running juried craft shows in America. Over 170 artists and makers, live music, a family art tent, gourmet food vendors, and a silent auction. Fri–Sat 10am–6pm, Sun 11am–5pm. $11 adults / $10 seniors / under 16 FREE

Celebrate East Lyme on 7/18 from 1–10pm at Niantic Main Street and McCook Point Park, Niantic: East Lyme’s biggest celebration transforms Niantic’s Main Street into a spectacular seaside festival with 200+ vendors, multiple live music stages, kids’ activities, and the beloved St. John’s Carnival. The day ends with a spectacular fireworks display over Niantic Bay at 9pm. FREE

Midsummer Festival Concert on 7/24 from  7–9pm at Florence Griswold Museum lawn, Old Lyme: The beloved kickoff concert on the riverfront lawn of the Flo Gris launches Old Lyme’s Midsummer Festival weekend featuring Mass-Conn-Fusion. FREE

Rhythm & Roots Festival on 9/4–9/6  at Ninigret Park, Charlestown, RI: Labor Day weekend roots music festival with Cajun, zydeco, blues, country, bluegrass, and Americana on three stages. 2026 headliners: The Devil Makes Three, St. Paul and The Broken Bones, Margo Price, Preservation Hall Jazz Band, and Yonder Mountain String Band. From $135 (day)/weekend passes available

Summer Concerts on the Green in Madison on Sundays in the summer from 6–8pm at Madison Town Green: 7/12-8/30, 6-8pm. Bring lawn chairs and a picnic. No alcohol permitted. 

Maugle Sierra Vineyards on Saturdays & Sundays, 3–6pm throughout summer at Maugle Sierra Vineyards, Ledyard: Live music every weekend afternoon. Check social media for lineup. FREE

Surfridge Brewery on Thursdays, 6pm throughout summer.  Live music every Thursday evening at this shoreline brewery.

Saltwater Farm Vineyards Music Series in Stonington on select Sundays, Thursdays and special events throughout summer. Sunday Funday afternoons with live music and food trucks. Check website for schedule.

The Juke on Fridays & Saturdays, 8–11pm at The Juke. Deep River’s destination for original live music every Friday and Saturday night.

Music at the Mansion on Wednesdays in July, 7/1–7/22 from 5:30 – 8:30 at Wadsworth Mansion, Middletown: Live entertainment every Wednesday night in July on the mansion’s magnificent back lawn. Food trucks and picnics welcome.