HarborFest Expands to Sag Harbor's Steinbeck Park

HarborFest, Sag Harbor’s most anticipated event of the year, is back once again September 10–11, 9 a.m.–5 p.m., with fresh faces, an expanded event space and exciting new activities for all ages.

Filling in for 2022 HarborFest Chairman Rory McEvoy after an injury, Sag Harbor Chamber of Commerce President Ellen Dioguardi stepped in to lead this year’s event planning. She was key in organizing the 2022 HarborFrost in February, but HarborFest, she notes, is a much bigger event.

“For me, the entire thing has been a learning experience,” she says. “It’s an event that has a lot of history in Sag Harbor, so there’s always this cautious aspect to it of keeping everything the way it’s been that everybody loves but also trying to improve it, to move forward with new aspects to it, such as the fact that this year we’re going to be using Steinbeck Park as one of the spaces.”

With the recent Long Wharf redesign — adding an outer pedestrian walking path at the cost of the driving area’s width — came necessary changes to the layout of the annual HarborFest. The Southampton Town Showmobile used for the big Saturday night concert would be incompatible with the tighter space, and thus had to be relocated to John Steinbeck Waterfront Park. This switch led to more HarborFest attractions moving to Steinbeck Park, such as the Kids’ Zone petting zoo.

“We all agreed that it’s a nicer setting to have (the petting zoo) in a park where there’s actually dirt and grass instead of asphalt with straw on it,” Dioguardi says. “So we’re going to have that, which also enabled us to bring in the pony rides, which were too problematic to do on the Long Wharf.”

HarborFest 2022 Activities

The Kids Zone features Tony the Pony and his Barnyard Buddies, plus additional fun and games from John Jermain Memorial Library and the South Fork Natural History Museum.

HarborFest’s kickoff is on Friday night, September 9, with a concert featuring The Complete Unknowns at Bay Street Theater. Then the festival begins in earnest on Saturday and Sunday with two full days of activities planned by the Sag Harbor Chamber of Commerce and other Sag Harbor businesses and organizations. While there are certainly things to do throughout the village, the main festival events will take place along Main Street, in Marine Park and Steinbeck Park, and on the Long Wharf and Windmill Beach.

“It’s a community effort,” Dioguardi says. “Like they say, ‘It takes a village,’ and HarborFest is definitely one of those things that it takes a village to make happen and to have it be the event that everybody looks forward to.”

Some of the chamber event highlights are outdoor concerts showcasing Alfredo Merat, Gene Casey and the Lone Sharks and the HooDoo Loungers; the annual clam chowder contest; a tour of the Old Whalers Church; a Taste of Sag Harbor; the annual Arts and Crafts Fair that’s expected to comprise a record number of vendors; and fire juggling by Keith Leaf.

Affiliated events include a celebration of Sag Harbor women at Sag Harbor Whaling & Historical Museum; a new Eastville Historical Society exhibition, as well as a book launch and signing with Dr. Patricia Turner; American Beauty cruises and charters; Historical Harbor Tours benefitting Fighting Chance cancer counseling; dramatic readings of John Steinbeck’s work by Harris Yulin, Paul McIsaac and others; and a celebration of Ma’s House as they receive Preservation Long Island’s Preservation Award for Organizational Excellence.

“It’s always been a goal of the chamber — at least as long as I’ve been involved with it — to infuse some of Sag Harbor’s history into this event,” Dioguardi notes, clarifying later that “the Whaleboat races are, in my opinion, truly the heart of this event in a lot of ways.”

HarborFest Whaleboat Races

For many longtime HarborFest attendees and Sag Harbor locals, the most exciting element of the annual event is the fierce competition of the Whaleboat races. Each year, teams of four — split into the Junior, Women’s, Men’s and Firefighters’ Cup divisions — row out into the harbor to harpoon the great white whale. Since the Whaleboat races’ start in the 1960s, it’s become something of a tradition, which can be a blessing but also a challenge.

“It’s just a hard thing to do because the tradition of Whaleboat racing is really passed down — like Ray Pettigrew had his daughter doing it,” Dioguardi says. “It gets passed down from family member to family member, in a way, and as people aren’t here — as the younger generations aren’t living here anymore, to all the different things that affects — we’re seeing it affect the Whaleboat races, because we don’t have a lot of those families that have traditionally always done it.”

Some past competitors have also passed on since their racing days. Joe Early died in May 2022, making this many locals’ first-ever race without his physical presence. He will be there in spirit, however, as his family is arranging a memorial as part of the event. “It’s sort of a testament to what that particular part of HarborFest means to people who have lived here a long time,” Dioguardi says.

With many past competitors and champions unfortunately unable to race this year, it leaves the door open for new faces, young and old up-and-comers ready to take on this time-honored tradition. What some may not realize is that the event isn’t even restricted to Sag Harbor residents.

Just about anyone can form a team of four and register to compete by emailing Gavin Menu at gmenu@expressnewsgroup.com or calling 631-725-1700 before the event starts on Saturday. And businesses are welcome to assemble more than one team — like The Corner Bar in Sag Harbor, which is expected to confirm four teams by race day.

While practice isn’t mandatory, it is certainly advised. “I don’t even think I fully got in the boat ever,” Dioguardi says of her only time competing, when she was drafted as a last-minute replacement. “I think I basically did the entire Whaleboat race hanging on to the side of the boat. So that would point to me that some practice is a good thing.”

After registering, a team can visit The Corner Bar to inquire about borrowing oars and a boat. Practicing with the HarborFest equipment is permitted in the days leading up to Saturday, September 10.

There’s much to look forward to at this year’s HarborFest, and it’s all happening in the temperate month of September. Dioguardi adds, “September really is the most beautiful month out here, so it gives everybody a chance to enjoy it in Sag Harbor.”

To learn more about HarborFest in Sag Harbor, visit sagharborchamber.com.