Summer Soundtrack: Top 2025 Concert Series in Fairfield County

above: Lainey Wilson performed at the Hartford Healthcare Amphitheater in June 2024.

 

HARTFORD HEALTHCARE AMPHITHEATER
Located in Bridgeport on the bank of the Long Island Sound, the 5,700-seat Hartford Healthcare Amphitheater, winner of the Best of Connecticut Music Venue,  is excited to launch its fifth season this summer with an extensive lineup of more than 40 shows featuring performance artists of all kinds, with some big names such as comedian Jerry Seinfeld, country singer Bailey Zimmerman (this one is sold out!), James Taylor, Barenaked Ladies, Counting Crows, Chicago, Toto and even Ringo Starr and His All Starr Band, because, as Alyse Goodman, the venue’s director of marketing and PR says, “Everyone should see one of the Beatles at least once in their life!” (I wholeheartedly agree.)

In addition to a wide range of performers, the venue also features other events, like the Connecticut Pizza & Brew Fest with Brown Roofing which the venue says is the ultimate pizza tasting in the state; this festival offers samples of some of the best pizza and craft beers Connecticut has to offer, as well as panel discussions, live music and pizza contests.

Beyond the performances, the food and concessions here are worth mentioning, as the amphitheater offers what Goodman says are “hyperlocal” options, ranging from local food trucks, sushi, pizza and more from local establishments like Garden Catering (hello, best chicken nuggets around), Nordic Fish, Bona Bona Ice Cream, Walter’s Hot Dogs, Layla’s Falafel, Donut Crazy, Hoodoo Brown, and more.

The season will run May to October, and tickets are available on hartfordhealthcareamp.com.

The outside of the amphitheater features upcoming artists.

LEVITT PAVILION
Westport’s beloved Levitt Pavilion, with support of sponsors like Yale New Haven Health, is looking forward to the upcoming 2025 season, which will run from May into October, and will, as always, feature both paid-ticket shows and its signature “50 free shows” under the stars.  The Levitt Pavilion, an independent and unique non-profit arts presenter, continues to produce one of the longest-running outdoor arts festivals in the nation in its iconic outdoor home along the banks of the Saugatuck River.

The soaring skies above the iconic amphitheater are mirrored by the constellation of artists — from the acclaimed and award-winning to rising stars ­— who light up the Epstein Stage all season long. Some highlights from the upcoming Stars on Tour Series will include sizzling jam band Pigeons Playing Ping Pong and pyrotechnic bluegrass outfit the Infamous Stardusters joining forces with NYC indie-funk band Melt in June. July promises to be a big month at the venue as well, with the electric improv-rock band Umphrey’s McGee returning as a stop on their Cruising Altitude Tour; the ever-popular, Michael Franti, promising a “high energy show bursting with positivity and music that spans hip hop, funk, reggae, jazz, folk and rock,” according to Levitt Pavilion VP, Executive Producer Carleigh Welsh; female folk trio I’m with Her comprising award-winning and acclaimed singer/songwriters Sarah Jarosz, Aoife O’Donovan and Sara Watkins come together again for a long-awaited tour and in support of their newest album Wild and Clear and Blue, along with Ken Pomeroy — a Cherokee songsmith hailing from Moore, Oklahoma who bends and braids stories of home, heritage and heartache and whose pen spills raw truth, turning trauma into anthems that whisper, “You’re not alone.” Fun fact: Pomeroy’s mamaw gave her a Cherokee name that means “Little Wolf with Yellow Hair,” and her song “Coyote” prowls with the same wild grace. There are plenty more events through August and into September as well.

Some of the noteworthy free shows at the Levitt will be Dogs In A Pile on June 20, and Low Cut Connie performing on August 2. Additionally, the popular free children’s series will return this summer as well, with fun music and dancing for all ages. Grab a pizza, a blanket, and bring the kids for a fun night out of music and dancing along the Saugatuck.

The Wood Brothers with The Bygones performed at the Levitt Pavilion in June 2024.

LACHAT FARM, MUSIC IN THE MEADOW CONCERT SERIES
Weston’s Lachat Farm has been hosting lively outdoor music acts on their beautiful 40-acre property for 10 years now, and this summer will be no different. Their once monthly Music in the Meadow Series hosts national touring acts across genres including folk, reggae, bluegrass, indie, pop, soul and funk. Their annual performance by the Stella Blue’s Band, the region’s premier Grateful Dead tribute act and the house band at Garcia’s at the Capitol Theatre (named after erstwhile Grateful Dead leader Jerry Garcia), has become a must-attend event and is a near instant sell-out every year.  This year Stella Blue’s Band visits the farm on September 13, and the other acts slated to perform on June 14, July 12 and August 23 will be announced soon.  All shows take place from 6-9 p.m., and food trucks and their Barn Bar will be open and available.  Ticket sales begin on April 4 and are available at lachattownfarm.org.

Drew Angus and his band perform at Lachat Farm.

THE WESTPORT FARMERS’ MARKET
On Thursdays from 10 a.m. to 2 p.m., the Westport Farmers’ Market offers some outdoor music options this summer when it opens in its spring/summer location at 50 Imperial Ave., in May. Through its partnership with Park City Music Hall, which WFM Executive Director Lori Cochran-Dougall says, “showcases the value of local organizations working together to strengthen our missions and community,” some of the featured artists include: John Torres & Ian Tait of Wild & Company; Previn & Kiran Edwards of Residual Groove; Benny Mikula of Alpaca Gnomes; Fuzz Sangiovanni of Deep Banana Blackout and Caravan of Thieves; and Dan Carlucci of Hitch & the Giddyup.

Additionally, WFM partner Park City Music Hall in Bridgeport, has a solid lineup of their own slated for May and June, including Sister Sparrow & the Dirty Birds on May 9, Amish Outlaws on May 10, The Moonrise Cartel on May 22, and a Dave Matthews Tribute Band on June 7.

Local DJ, Doey Joey aka Joe Milazzo at The Westport Farmers’ Market.

Photographs: Amphitheater by Katie Settel; Lachat farm by Bruce Plotkin Photography; Levitt pavilion by John Shyloski

 

 

 

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