Top North Fork Events This Weekend: Greenport Maritime Festival, Broadway, Live Music and Fall Fun, Oct. 16-18

From a major waterfront celebration to Broadway performers, autumn festivals and a few unexpected outings, here’s where to go and what to do across the North Fork and Shelter Island this weekend.

The North Fork is making the most of October, with Greenport’s 36th annual Maritime Festival finally taking over the village after its September postponement. Beyond the waterfront, Broadway performers head to Mattituck, Riverhead Raceway gets into the Halloween spirit, and Shelter Island hosts its annual fall race for women’s cancer charities. Here’s what’s happening Friday, Oct. 16, through Sunday, Oct. 18.

EDITOR’S TOP 5

1. 36th Annual Greenport Maritime Festival
2. Broadway in the Vines at Rose Hill Vineyards
3. Halloween Havoc at Riverhead Raceway
4. Shelter Island Fall 5K Run/Walk
5. Three Sonatas for Violin and Piano at North Fork Arts Center

FESTIVALS & FAMILY FUN

36th Annual Greenport Maritime Festival
Saturday-Sunday, Oct. 17-18. Parade Saturday at 11 a.m. Free admission to main festivities.
Mitchell Park, 115 Front St., and throughout Greenport Village

Greenport’s signature waterfront festival returns after September’s postponement, with a maritime parade, community rowing, pie-eating contest, fishing derby, treasure hunt and hot sauce competition. Sunday’s highlights include a fish-filleting contest, the Cardboard Boat Regatta at 12:30 p.m. and the Work Boat Race at 1 p.m. It’s a full weekend celebrating the village’s working waterfront and maritime heritage.

Maritime Land & Sea Gala
Friday, Oct. 16, 6-9 p.m. $125.
Greenport American Legion, 102 Third St., Greenport

The Maritime Festival kicks off with an evening of food, drinks and dancing, featuring tastings from local restaurants. Originally planned for Mitchell Park, the gala has been moved indoors to the American Legion because of the weather forecast.

Halloween Havoc at Riverhead Raceway
Saturday, Oct. 17. Ticketed; check website for schedule.
Riverhead Raceway, 1797 Old Country Road, Riverhead

A Halloween-themed Day of Destruction featuring a school bus demolition derby, flagpole racing and a pit party where children can trick-or-treat and meet drivers. Costumes encouraged.
Website: https://riverheadraceway.com/events/view/741

34th Annual Aquebogue Fall Festival
Sunday, Oct. 18, 10 a.m.-4 p.m.
Aquebogue Elementary School, 499 Main Road, Aquebogue
The Aquebogue PTO hosts its annual community fall festival, bringing families together for seasonal activities and autumn fun.

Mattituck-Laurel Library Pumpkin Celebration
Friday, Oct. 16, 5-7 p.m.
Mattituck-Laurel Library, 13900 Main Road, Mattituck

An evening of pumpkin displays, games, crafts, face painting, balloon twisting and popcorn. The library’s singing pumpkins return, along with jack-o’-lanterns decorated by local families.
Website: https://www.mattitucklaurellibrary.org/

MUSIC & PERFORMANCES

Broadway in the Vines
Friday, Oct. 16, 6:30-8 p.m. $95.
Rose Hill Vineyards, 2000 Oregon Road, Mattituck

Broadway performers Kate Rockwell, Krystina Alabado and Ryann Redmond bring musical theater favorites to the vineyard for an intimate concert. Wine and light bites will be available for purchase. Rain or shine.

Three Sonatas for Violin and Piano
Saturday, Oct. 17, 7-9 p.m. $40; free for ages 25 and younger.
North Fork Arts Center, 211 Front St., Greenport
Violinist Robert Chausow and pianist Eleonor Bindman perform sonatas by Bach, Beethoven and Grieg at Greenport’s restored theater.

Uptown: A Celebration of Motown & Soul
Friday, Oct. 16, 8 p.m. Ticketed.
The Suffolk, 118 E. Main St., Riverhead

A lively celebration of Motown hits and soul classics at Riverhead’s restored Art Deco theater.
Website: https://www.thesuffolk.org/

The Perlman Music Program: Alumni Recital With Nathan Meltzer
Saturday, Oct. 17, 5 p.m.

The Perlman Music Program, 73 Shore Road, Shelter Island Heights
Violinist Nathan Meltzer returns to the Perlman Music Program for an alumni recital,

The Perlman Music Program: Alumni Works in Progress Concert
Sunday, Oct. 18, 2 p.m.

The Perlman Music Program, 73 Shore Road, Shelter Island Heights
Musicians from the program’s alumni community share works in progress in an informal concert setting.
Website: https://perlmanmusicprogram.org/

FOOD, ART & CULTURE

Peeko Oysters: Tasting, Talk & Tour
Saturday, Oct. 17, 2 p.m. Ticketed.
Peeko Oysters, 900 First St., New Suffolk

Go behind the scenes of North Fork oyster farming with a waterfront tour, a discussion about raising oysters in local waters and a tasting.
Website: https://www.peekooysters.com/

Concert at the Caboose: The Mudflats
Sunday, Oct. 18, 2 p.m. Free.
Railroad Museum of Long Island, 440 Fourth St., Greenport
The Mudflats perform a free concert at the historic railroad museum as part of Greenport Maritime Festival weekend.
Website: https://www.rmli.org/

BENEFITS & COMMUNITY

27th Annual Shelter Island Fall 5K Run/Walk
Saturday, Oct. 17, 11 a.m. $50 race-day registration.
35 Shore Road, Shelter Island

The scenic 3.1-mile race supports the North Fork Breast Health Coalition, the Coalition for Women’s Cancers and Lucia’s Angels, helping women affected by cancer on the East End. The event includes a post-race barbecue, with shuttles available from the ferry terminals.
Website: https://www.shelterislandfall5k.com/

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 .