Sag Harbor’s 2021 HarborFest Promises to Be Best Yet

Team Whalers going after the white whale in the 2015 HarborFest Whalers Cup
Team Whalers going after the white whale in the 2015 HarborFest Whalers Cup
Barbara Lassen

Somewhere in the Dan’s Papers archive there’s a collection of photos taken in March 2020 that showcases the friendly, smiling faces of Sag Harbor’s charming community; unfortunately, those images were never used, as it suddenly became taboo to show anyone smiling without a mask. With that paradigm shift, came the sad cancelation of HarborFest in September 2020 and HarborFrost in February 2021, the two biggest annual events on Sag Harbor’s calendar. But now, finally, the vaccinated among us can show off our smiles once more, and there’s certainly a reason to smile, because HarborFest 2021 is a go this weekend!

The Sag Harbor Chamber of Commerce, which recently underwent a change in leadership and introduced new board members, is welcoming visitors and locals to three days of fun in the usually serene village.

“A transition like that can be challenging, but we really worked together and really planned a terrific festival for this year,” says Gavin Menu, chamber president and publisher of the Express News Group, emphasizing the vital role that chamber treasurer and HarborFest committee chairman John J. Leonard played in organizing the event. “Since it is a new group of leadership, we’re hoping to add our own mark on it — some new events, new surprises — and really carry the tradition into the new organization.”

The festivities begin with a bit of a pre-party on Friday, September 10, with the annual Moby Dick Marathon, usually a separate summer event, now kicking off HarborFest. That night, Bay Street Theater’s Title Wave: New Works Series begins, featuring readings of new plays in development, providing playwrights with invaluable insight into the audience’s response. Then, on Saturday and Sunday, the core festival officially begins when Marine Park and Long Wharf come alive with activities for kids and adults, foodies and music-lovers, shopaholics and adrenaline junkies.

Long Wharf will be teeming with cool kids’ activities all weekend long, including bounce castles, games, competitions, amusements and much more. A new attraction this year is the Barnyard Buddies petting zoo, where children can meet farm friends such as bunnies, sheep, ponies and more. A few yards away at Windmill Beach, there will be contests aplenty — tug-of-wars, hula hoops and corn shucking, too.

The HarborFest Clam Chowder Contest returns with new chowders to sample, each made by a local restaurant, bursting with flavor and designed to win its restaurant the $500 prize. It costs $18 to participate on Sunday at noon, and the cost includes a commemorative HarborFest mug. Proceeds benefit the Sag Harbor Chamber of Commerce.

The famous HarborFest Clam Chowder Contest will return to Long Wharf on Sunday, September 12, starting at noon. Michael Heller
The famous HarborFest Clam Chowder Contest will return to Long Wharf on Sunday, September 12, starting at noon.Michael Heller

The East End has a number of beloved musicians and bands, and on HarborFest weekend you’ll find many of them playing the Sag Harbor scene. Jim Turner and the Sag Harbor Community Band return to the Long Wharf stage, while The Popsicles and The Steven Tekulsky Band get set for their debut HarborFest shows. On Saturday night, the village will be treated to the folk rock heart of Gene Casey & the Lone Sharks and the New Orleans soul of the HooDoo Loungers — two of the most popular acts in the area.

Fans of the 2021 Father’s Day Weekend Arts & Crafts Fair will be happy to learn that the fall fair has returned, as well. Located among the yachts in Marine Park, the HarborFest Arts & Crafts Fair offers jewelry, clothing, artwork, photography and other luxurious goods from about 50 local vendors. The Long Wharf will feature even more vendors — these ranging from nonprofits to boat clubs to the Boy Scouts.

While the annual HarborFest attracts attendees for myriad reasons, for many, it means one thing above all else: a chance to compete in the Whaleboat Races and claim the coveted Whalers Cup and all the bragging rights that come with it. Dating back to the Old Whalers Festival that began in 1964 to boost fall tourism, the Whaleboat Races have evolved to include divisions for men, women, juniors and firefighters. Races begin at noon on Saturday and 11:30 a.m. on Sunday, and run throughout the afternoon, leading to the adrenaline-fueled championship races at 3:30 p.m. on Sunday.

This year’s race is already shaping up to be a heated competition, with some longtime champions ready to take on new challengers and others ready to share the spotlight. To many fans’ surprise, 19-time Whalers Cup champion Team Whalers will be sitting out the 2021 race, which means the men’s division could be anybody’s game. Though several East End fire department teams have vied for victory in the firefighters’ division, the Sag Harbor Dive Team has, according to Menu, “won it every year for as long as I can remember.” Maybe this is the year the streak is broken. Anyone interested in entering a team in any of the four divisions must attend the captains’ meeting at noon on Saturday and submit payment of $50 and a completed registration form either at the meeting or via email to Menu at [email protected].

For those more comfortable racing on land, the Parks and Recreation Association of Sag Harbor is launching a new annual 5K run/walk to help raise money for Mashashimuet Park improvements. This year’s race, “A Grand-run for the Grandstand,” is raising money for the refurbishment of the park’s grandstand, which was built in 1908. The epic run (or leisurely walk) begins at 8:30 a.m. on Saturday, and anyone interested should register at

“I’m really proud of the business community of Sag Harbor in general and the way that they’ve come together, supported each other and persevered over the last 18 months,” Menu says, adding that HarborFest is a great way to support this incredible, steadfast community. “It’s just going to provide a really great boost of joy and excitement during what has otherwise been a difficult time.”

For am up-to-the-minute schedule of events, see page 91 or visit

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