Adam Epstein is on the road. At the moment he is in Boise, Idaho, tired and a bit burned out, but his traveling companion is David Sedaris.

“If you have to travel, he’s the one to do it with,” Mr. Epstein said.

Mr. Epstein and his wife Mandy run Innovation Arts Entertainment and produce over 300 shows a year all over North America. So although the company is based in Chicago, he is on the road most of the time. He began producing shows for Mr. Sedaris 16 years ago, after laughing so hard he almost choked while reading one of Mr. Sedaris’s books. And for the past two summers, Mr. Epstein has brought Mr. Sedaris to the Vineyard to perform shows at the Old Whaling Church and the Performing Arts Center.

The shows went so well, Mr. Epstein has decided to up the ante for summer 2016 by creating the Martha’s Vineyard Concert Series, in partnership with the Vineyard Gazette. This summer’s lineup includes eight different performers so far, including Alan Cumming, Erin Brockovich and Paula Poundstone.

Mr. Epstein and his wife bought a home in Katama two years ago, but he has been coming to the Island for decades. He first visited after his freshman year in college.

“I worked for a garbage man in Vineyard Haven,” he said, adding that he was hooked on the Island immediately. And when you get hooked while hauling garbage, well, that relationship is for real.

Going from one performer to a whole calendar of events all summer long is a big leap, Mr. Epstein acknowledges, and it comes with some risk.

“You have to guarantee the artist’s fee,” he said. “So if you sell out or just sell one ticket the expenses are the same.” Plus, the standard Vineyard barriers to entry are always looming — high transportation and housing costs.

But producing shows has been in Mr. Epstein’s blood for a long time, ever since he shifted from pursuing a Ph.D. in developmental psychology. On the side he tried his hand at producing one show, a Bob Dylan concert. It was so much fun he never looked back.

Mr. Epstein’s philosophy is to make the experience both great for the audience and the performer.

“If I get the artists to love it, the place and the experience, they will want to come back,” he said. And they will tell their friends, like Mr. Sedaris does.

“David loves it on the Vineyard. Each year he asks me if he can come back.”

Mr. Epstein is excited about this summer and is bringing his whole staff out in late May to get to know the Island. He also has a wish list of performers he wants to add to the roster. Chief among them is Jerry Seinfeld.

“He could come to workshop material on the Island,” Mr. Epstein said.

He is also still looking for a hotel to come on board as a sponsor to help with housing the performers.

“It’s all a means to an end,” Mr. Epstein said. “My goal in all this is to be able live on the Vineyard full time. It’s just too hard to leave.”

For more information and tickets visit The current list of performers is Paula Poundstone on July 1, Erin Brockovich on July 7, Preservation Hall Jazz Band on July 19, Alan Cumming on July 20, David Sedaris on July 26 and 27, Amy Goodman on July 30, The Moth on August 3, The Capitol Steps on August 21 and Celebrity Autobiography on August 23.