Sail into the End of Summer with Harborfest in the Hamptons

A classic Sag Harbor Tradition since the 1960's, Harborfest is a two-day event that brings together the East End for whaleboat races, live music, chowder sampling, arts & crafts, and more. It is easily one of the most anticipated community events in The Hamptons—just ask BHS Hamptons Agent and former whaleboat racing champion, Jane Holden!

Jane Holden and her BHS Whaleboat Teammates in 2017

"Harborfest first began in the 1960s as the 'Old Whalers' Festival.' It included the whaleboat races we still hold to this day, as well as a parade featuring the Sag Harbor Community Band. As part of the parade, two very large, wooden whales would be pulled down Main Street to the delight of adults and children alike."— Jane Holden

The Whalers' Festival became such a popular community event that the local chamber of commerce decided to rebrand and utilize it to draw visitors to the area. Thus, Harborfest was born. It has since blossomed into a beloved community tradition that showcases all the East End has to offer residents and visitors alike.

Taking place this year on September 10th and 11th, today's Harborfest mimics many of the qualities of the Whalers Festival. The Community Band now plays along the Long Wharf, rather than marching down Main Street, along with several local bands and singers. The festival also features a presentation from the U.S. Coast Guard and the 'Taste of Sag Harbor' series, which showcases the best of the area's dining.

In exchange for a charitable donation to the local food pantry, attendees also have the chance to sample clam chowder from several nearby restaurants and vote for their favorites.

Easily the centerpiece of Harborfest, the whaleboat races are marked by one of the Whalers' Festival's original wooden whales, which floats in the harbor throughout the event. Open to public participation—juniors and adults—the races are as fun as they are competitive. Holden was proud to take home the crown alongside her BHS team members in 2017!

To register for the race, call the Sag Harbor Express at 631-725-1700. Boats are available for practice on the Monday before the event, and the teams who win on Saturday compete in the finals on Sunday. — Jane Holden

Another Harborfest event worth considering is the Arts & Crafts Fair, which is bound to be fun for the whole family. Children and adults alike can gaze in awe at jaw-dropping exhibitions and even make their own creations to take home.

Other highlights include sunset cruises in the harbor, a children's beach hula-hooping session, and a Sunday pancake breakfast.

See the full Harborfest 2022 schedule. Connect with Jane E. Holden and view her current listings here.