Sign up for our Newsletter

HarborFest is an annual weekend-long festival that honors the maritime history of Sag Harbor. (Photo courtesy of Sag Harbor Chamber of Commerce)

As we’ve said before — more than once, but who’s counting — September is arguably the best month of the year here on the South Fork. Testament to that is the annual HarborFest that comes to Sag Harbor this weekend, giving locals and visitors a village-wide, end-of-summer celebration following the hustle and bustle surrounding Labor Day. The two-day long festival, scheduled for this Saturday, September 16, and Sunday, September 17, centers around the longstanding traditions of the old whaling village, with several nautical nods to its rich maritime history.

Kids can participate in tug-of-war contests, potato sack races, corn shucking contests and more throughout the weekend. (Photo courtesy of Sag Harbor Chamber of Commerce)

While Long Wharf and adjacent Windmill Beach serve as the main base for festivities, attendees can expect plenty of fun events scattered all around town, all weekend long. There’ll be tons of local favorites for food and drink, plus games, contests and activities for folks both young and old, as well as historical talks and tours, arts and craft fairs, live music, boat charters and the highly-anticipated signature event, the whaleboat races.

“Anyone wanting to get a good idea of what Sag Harbor is about should take a stroll down Long Wharf and see all the vendor booths,” says Ellen Dioguardi, president of the Sag Harbor Chamber of Commerce. “From the Sag Harbor Food Pantry and the Eastville Community Historical Society to the local Boy Scout Troop and dozens of other organizations, not for profits and local businesses, the community of Sag Harbor is fully represented at HarborFest.”

Kicking off at 9 a.m. on Saturday is an arts and crafts fair at Marine Park, situated on Bay Street. The fair will run from 9 a.m. to 5 p.m. both days. A few steps east is the weekly Sag Harbor Farmers Market from 9 a.m. to noon, offering some of the most highly coveted local produce and products from across the East End. Long Wharf will be bursting with activity, as it holds the Taste of Sag Harbor both Saturday and Sunday from 10 a.m. to 5 p.m., with over a dozen food tents and trucks offering both food and drink from some favorite Sag Harbor eateries and organizations.

“HarborFest is about community… it’s a very thick thread in what makes the fabric of Sag Harbor so unique and wonderful.”

Ellen Dioguardi, president, Sag Harbor Chamber of Commerce

Classic boats will be on display around the perimeter of the Wharf while a slew of live talks, exhibitions and tours are slated for Steinbeck Park, Old Whalers’ Church, Sag Harbor Cinema, the Whaling Museum, and the Eastville Historical Society Heritage House, among others. Attention Harbor shoppers! This is also a great opportunity to peruse the downtown shops, as most will have outdoor displays of their unique wares.

Professional fire juggler Keith Leaf is on tap to perform during the weekend’s festivities. (Photo courtesy of Sag Harbor Chamber of Commerce)

The Sag Harbor Community Band, Gene Casey and the Lonesharks, Alfredo Merat, the HooDoo Loungers, and Annie Trezza are among the musical talent slated to perform throughout the weekend, while boat cruises and charters on the American Beauty and Luna schooner will be available beginning at 10 a.m. and continuing into the evening. Both boats are scheduled to tour around the neighboring Barcelona Point, Cedar Point Lighthouse and Shelter Island’s Mashomack Preserve.

“When I say it takes a village to make this event all it is, I don’t just mean those of us who work on putting it together behind the scenes, although that is a loyal and hardworking group. It also includes the people who show up every year to cheer on the whaleboat teams, the parents watching their kids in their first tug-of-war challenge, the clam chowder tasters who vote for the best chowder,” Dioguardi says. “HarborFest is about community and for me as a 41-year resident of this area and president of the chamber, it’s a very thick thread in what makes the fabric of Sag Harbor so unique and wonderful.”

Sunday morning starts at the Sag Harbor Fire Department (1357 Brick Kiln Road) as they host a pancake breakfast starting at 8 a.m. while the annual whaleboat races culminate with the men’s and women’s championships off Windmill Beach at 3:30 p.m. on Sunday. Winners get the coveted Whalers Cup and ultimate bragging rights.

Men, women, and firefighters all compete for the coveted Whaler’s Cup, and ultimate bragging rights, in the annual whaleboat races at Windmill Beach. (Photo courtesy of Sag Harbor Chamber of Commerce)

For the kids, there’ll be a bouncy house set up along the Wharf, as well as several contests and races, plus a show from expert fire juggler Keith Leaf.

For the full schedule of events happening this weekend, click here.

New for this year will be a tribute to the late great American author and former Sag Harbor resident John Steinbeck, in honor of the newly completed park that bears his name located at the foot of the bridge. According to the chamber, Steinbeck was one of the founders of the Old Whalers Festival, a precursor to HarborFest that began in 1964 as an effort to drum up tourism during the shoulder season.

“To know that the hand of author John Steinbeck probably touched the first whaleboat oarlocks as he helped create the original Whalers Festival is something that never fails to make me proud Sag Harbor has continued this annual event, with all its updates and changes,” Dioguardi says. “At its heart, it is still about honoring the history of this village and coming together as a community.”