Sag Harbor HarborFest 2026: Whaleboat Races, Live Music, Schooner Sails and More

The annual waterfront festival returns Sept. 19-20 with whaleboat races, the fall arts and crafts fair, clam-shucking and chowder contests, live music, food, family activities and Sag Harbor maritime traditions

Sag Harbor goes full maritime for HarborFest 2026, returning Saturday and Sunday, Sept. 19-20, with two days of events stretching from Long Wharf and Windmill Beach to Marine Park, Steinbeck Park and Main Street.

The annual fall weekend celebrates the village’s whaling and maritime history while bringing plenty of present-day Sag Harbor fun to the waterfront — whaleboat races, schooner sails, live music, local food, beer and wine, an arts and crafts fair, classic boats and some seriously competitive clam shucking and chowder tasting.

Here are some of the highlights worth catching.

The Whaleboat Races

One of HarborFest’s signature traditions returns to the waters off Long Wharf and Windmill Beach.

Elimination rounds begin Saturday at noon and continue at 3 p.m. On Sunday, the Firefighters’ Cup Whaleboat Race begins at 11:30 a.m., followed by the semifinals at noon and the men’s and women’s championship races at 3:30 p.m.

Fall Arts and Crafts Fair

The Sag Harbor Chamber of Commerce’s Fall Arts and Crafts Fair takes over Marine Park from 9 a.m. to 5 p.m. Saturday and Sunday, with artists and artisans selling paintings, pottery, photography, jewelry and other handmade work against the waterfront backdrop.

Sail Sag Harbor

Want to experience HarborFest from the water? The 74-foot schooner Luna, part of the SailHamptons fleet, will offer sails from Long Wharf throughout the weekend.

Saturday departures include 90-minute sails at 1 and 3 p.m., plus a 5:30 p.m. sunset sail. Sunday sails depart at 1 and 3 p.m. Tickets range from $80 to $100 per person.

Clams, Chowder and a Taste of Sag Harbor

Come hungry.

A Taste of Sag Harbor runs from 10 a.m. to 5 p.m. both days on Long Wharf.

Saturday brings the HarborFest Clam Shucking Contest at 2 p.m., while Sunday’s Clam Chowder Contest begins at noon. A $25 ticket for the chowder competition includes a commemorative 2026 HarborFest mug and benefits the Sag Harbor Chamber of Commerce and Sag Harbor Cinema.

Live Music All Weekend

There’s music throughout the village, with performances at Steinbeck Park, Bay Street Theater’s courtyard and Long Wharf.

Saturday’s lineup includes the Sag Harbor Community Band, Julia King, Bonac Strings, Bryan Gallo, M Takes the Mic, Gene Casey and The Lone Sharks, and The HooDoo Loungers.

Sunday brings Brad Penuel, George Howard & The Moderators, Alfredo Merat, Mighty Ramon & The Phantoms of Soul, ECC & The Constituency and The Scofflaws.

Saturday night, Nancy Atlas, her band and special guests take over Bay Street Theater for The Howl, a one-night concert benefiting music programs at Pierson Middle-High School through Atlas for the Arts. The show begins at 8 p.m.; tickets are $65.

Sag Harbor History Comes Alive

HarborFest isn’t only about what’s happening on the waterfront.

The Sag Harbor Whaling and Historical Museum hosts its annual “725” Art Show & Sale throughout the weekend, featuring artists who live within Sag Harbor’s old 725 telephone exchange.

On Sunday, the Old Whalers’ Church offers a tour at 9 a.m., followed by a special living history service at 10 a.m. At 11:30 a.m., historian Zach Studenroth leads a tour of the historic Old Burying Ground next door.

The Eastville Historical Society Heritage House and historic St. David AME Zion Church will also be open during the weekend, with exhibitions exploring local history.

For the Kids

HarborFest remains very much a family affair, with children’s amusements and games at Long Wharf and Windmill Beach both days.

Look for tug-of-war, corn shucking, potato sack races, hula hoop activities and a Sunday afternoon fire and juggling show with Keith Leaf. The Wharf Shop will also offer its annual rocking dory photo opportunity for little captains.

Start the Weekend Friday Night

HarborFest officially gets underway early with a Friday evening cocktail party at the historic Hannibal French House, an Italianate Main Street home and one of Sag Harbor’s architectural standouts.

The Sept. 18 party runs from 5 to 7 p.m. and benefits the Sag Harbor Historical Museum. Tickets are $200.

IF YOU GO

Sag Harbor HarborFest 2026
Saturday and Sunday, Sept. 19-20
Events throughout Sag Harbor, including Long Wharf, Windmill Beach, Marine Park, Steinbeck Park and Main Street

For the complete HarborFest schedule and updates, visit the Sag Harbor Chamber of Commerce at sagharborchamber.com.

Schooner Luna tickets and information: sailhamptons.com

The Howl tickets: baystreet.org

Sag Harbor Historical Museum: sagharborhistoricalmuseum.org

Angela LaGreca

Editor, Co-Founder/Publisher

Angela LaGreca, Editor-in-chief and co-Founder/Publisher of Spark Hamptons, is a four-time Emmy Award-winning journalist, producer, writer and comedian/host. Her TV credits include NBC’s “Today,” ABC’s “The View,” and, most recently, the primetime cable news program “Cuomo” on NewsNation. On the East End, she was the Creative Director at LTV, VP Features/Events/Photo Editor at Dan’s Papers, and has performed at Guild Hall, Bay Street Theater and the WHBPAC. Her publishing career began at Modern Photography, where she was managing editor. LaGreca lives in Manhattan and East Hampton and can be reached at angelatvmedia@gmail.com and angela@sparkhamptons.com .