Fairfield Four, HillBenders Headline Sag Harbor American Music Festival

Selecting an opening night act for the Sag Harbor American Music Festival is something of a science, founder Kelly Connaughton Dodds explained.

The performers need to have a certain amount of clout. They need to fit into the nonprofit festival’s Americana roots. And they need the right sound that will take advantage of the Old Whalers’ Church’s stunning acoustics.

When Ms. Dodds heard The Fairfield Four was on tour, she said she had to have them.

The traditional, African-American, a cappella, gospel-style group, which is best known for its haunting performance in the film “O Brother, Where Art Thou?” will kick off the fifth annual music festival on Friday night, marking their first Long Island concert since the group was founded—in 1921.

“They’ve been around for almost 100 years—not these people, obviously, but in some form or another,” Ms. Dodds said of the four-man group, which now consists of Joe Thompson, Levert Allison, Larrice Byrd Sr. and Bobbye Sherrell. “They’ve influenced so many different kinds of music, especially the blues. To have them perform at the Old Whalers’ Church, it’s the perfect venue for them. It’s going to be a once-in-a-lifetime opportunity for many people.”

As it has been from the beginning, Saturday’s festivities are open and free to the public. More than 25 acts will descend upon Sag Harbor Village, starting with Escola de Samba BOOM at 11 a.m. Every half hour going forward, a new genre of music will hit Main Street and beyond, whether it’s rock, reggae, cabaret, jazz, folk, classical, singer/songwriter, Latin fusion, country, the blues and even hip-hop.

“The PitchBlak Brass Band is a hip-hop brass band. I’m sure people will be like, ‘What?’ But, really, people should come out and hear this,” Ms. Dodds said. “We’ve been trying to bring hip-hop into the festival since the beginning, and it hasn’t worked out until now. This is such a huge sound.”

Last year, the concerts drew approximately 2,000 music fans—though a precise headcount is nearly impossible, Ms. Dodds said. She said she expects this year to be even bigger.

“In the beginning, none of us had any idea how this was going to be received. And the community has been so supportive,” Ms. Dodds said. “It’s a dream. It’s better than we anticipated. This was our greatest hope. I’ve worked in nonprofits my whole career and for this to happen, at this level, in five years is not usual.”

What used to be the Saturday night after-party has morphed into a full-blown concert with The HillBenders of Springfield, Missouri, at Bay Street Theater. They will perform The Who’s “Tommy,” except as “A Bluegrass Opry,” which earned them national buzz after bringing it to South by Southwest. “It was this breakout performance,” Ms. Dodds said. “We read about it, we heard about it, and we immediately invited them.”

And, for the first time, the festival has expanded to include a Sunday gospel brunch at Harlow East, which will feature a performance by The Ron Crichlow Ensemble—a high-energy group of mostly childhood friends from Queens united by music. Adding a third day is ambitious, Ms. Dodds explained. But next year, it will resemble Saturday’s free concert series.

“At the end of the day, I do this because I love music. It’s a big part of my life, and this is my community. I wanted to give back, and I found a bunch of people who felt the same way,” Ms. Dodds said. “It’s a joy, and I hope someone will continue to carry this out beyond us. This is bigger than one person. The community has embraced it and I hope it will carry on for years to come.”

The fifth annual Sag Harbor American Music Festival will kick off with a performance by The Fairfield Four on Friday, September 25, at 8 p.m. at Old Whalers’ Church in Sag Harbor. Tickets are $25. A free, day-long concert series, featuring 28 acts, will be held on Saturday, September 26, from 11 a.m. to 9 p.m. at various locations in the village. In the event of rain, alternative locations will be available for all outdoor performances. That evening, The HillBenders will perform at 9 p.m. at Bay Street Theater in Sag Harbor. Tickets are $25. The festival will conclude with a gospel brunch, featuring a performance by The Ron Crichlow Ensemble, on Sunday, September 27, at Harlow East. Call (631) 725-5858 to make a reservation.

For more information about the weekend-long festival, visit sagharbormusic.org.