Enjoy the East End Al Fresco. 
From Riverhead to Orient to Montauk

The Eastern End of Long Island, New York City’s backyard beach getaway, offers a variety of fun activities for all ages and interests. From Riverhead to Greenport to Montauk, there are the Hamptons, North Fork farms and vineyards, breweries, scenic beaches, and stunning views. From tall ship festivals to music festivals to drag racing events, to the Long Island Aquarium, Splish Splash, and the Parrish Art Museum, there’s something for everyone.

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Week of Sept 14th

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Sag Harbor: Where Whaling History Sets Sail

Sag Harbor, nestled on the eastern end of Long Island, has a rich history of whaling that dates back to the late 17th century. Originally settled by European colonists in 1707, the town quickly became a center for the whaling industry due to its strategic location and deep harbor. In the 18th and 19th centuries, Sag Harbor thrived as a bustling whaling port, with numerous ships embarking on perilous journeys to hunt for whales in distant oceans. Today, the town's maritime heritage is preserved in its museums, historic buildings, and annual festivals, serving as a poignant reminder of its once-thriving whaling history.

Explore the rich history and natural beauty of the East End and plan your weekend in one of our towns (East Hampton, Montauk, Riverhead, Shelter Island, Southampton and Southold), visit eastendgetaway.com, your destination guide for all things on the East End Al Fresco.


HARBORFEST and Fall Arts & Crafts Fair

Sag Harbor.  |   Saturday,  September  16th. &  Sunday,  September 17th

The second of two Arts & Crafts events sponsored each year by the Sag Harbor Chamber of Commerce. The events take place in Marine Park against a backdrop of luxury yachts, one block from historic Main Street. Stroll along the waterfront to discover and purchase amazing works by a select group of artisans.


HarborFest 2023 will be held Saturday and Sunday September 16th and 17th, with the village’s rich maritime history on full display all weekend long. Long Wharf will be filled with live music, kids activities, great food, beer and wine and dozens of vendors representing Sag Harbor’s rich cultural and artistic history.

Visit Marine Park for the annual HarborFest Arts & Crafts Fair, with more than 50 vendors on hand to sell their handmade art, jewelry and other crafts. Don’t miss the famous HarborFest Clam Chowder Contest on Sunday at noon, and of course whaleboat racing all afternoon on both Saturday and Sunday off Windmill Beach.

Fun for Kids

New to HarborFest this year is an expanded Kids’ Zone in Steinbeck Park with Tony The Pony offering pony rides and a petting zoo for all children to enjoy. The South Fork Natural History Museum will be in Steinbeck Park with live native Eastern box turtles, and gray tree frogs, and John Jermain Memorial Library will have fun sea-themed crafts and tattoos. Don’t miss the fire juggling show by Keith Leaf at 3:45 pm on Saturday. Long Wharf will also be teeming with fun kids’ activities, with bounce castles, games, competitions, amusements and so much more. Just off the wharf on Windmill Beach will be tug-of-wars, hula hoop contests and the annual corn shucking contest, all presented by Epic Martial Arts.

Whaleboat Races

HarborFest’s signature event presented by The Sag Harbor Express off Windmill Beach, where annual bragging rights and the coveted Whalers Cups are on the line. The races had their origins in the Old Whalers Festival, which began in 1964 as an effort to drum up tourism during the shoulder season. Races begin at noon on Saturday and 11:30 am on Sunday and run throughout the afternoon. Men’s, Women’s, Junior’s and Firefighter divisions will compete.

Live Music on Long Wharf

This year’s festival will feature live music across town with musicians taking to Long Wharf, Steinbeck Park and the Sag Harbor Historical Museum throughout the day on both Saturday and Sunday. Old favorites like Jim Turner and the Sag Harbor Community Band, along with some new names like The Popsicles and Lynn Blue Band. Don’t miss Bruce Beyer & Friends at the Sag Harbor Historical Museum on Saturday at 2:00 pm. The festival wraps up on Saturday with a 5:00 pm performance by Gene Casey and The Lonesharks and a 7:00 pm show with the HooDoo Loungers, both in Steinbeck Park.

Clam Chowder Contest

The can’t-miss event of the festival is the famous HarborFest Clam Chowder Contest, which begins at noon on Sunday. Sample chowders from local restaurants and take home a commemorative HarborFest mug! The event is sponsored by Manna at the Lobster Inn, costs $20 to participate and will benefit the Sag Harbor Chamber of Commerce.

Tour the Old Whalers’ Church
Built in 1844, the Old Whalers’ Church is a National Historic Landmark at 44 Union Street in Sag Harbor. Starting at 9:00 am on Sunday, there will be an architectural highlights tour by Randy Croxton and members of the church’s historical committee. Listen to the sound of the oldest working pipe organ on Long Island, demonstrated by the church’s highly regarded organist and music director, Walter Klauss. Attend a church service at 10:00 am based on the words and music of the time period when this beautiful church was constructed and attended by whalers from around the world. Finish your visit with coffee hour and a historic tour of the Old Burying Ground, final resting place of patriots and Revolutionary War veterans.

Sunflower Festival

Harbes Family Farm, Jamesport   |   Saturday, September 16th  &  Sunday, September 17th   9a - 6p

Don’t miss two fun-filled days of fall fun and SUNFLOWERS! Get lost in a breathtaking sea of golden-yellow as you wander through the sunflowers. Don’t forget to grab those sunflower selfies!

Come make it the perfect Fall day! Our Jamesport Honeycrisp Apple Orchard has loads of delicious apples to pick. Our innovative trellis system allows us to grow apples that are even within reach of the smallest of hands! Don’t worry about having to walk far because our Apple Express will chauffeur you to the ripest rows of apples. While you’re here you can’t miss our Robin Hood Trivia Challenge Corn Maze! Our maze has a fun & challenging touchless trivia game. As an extra bonus game, you can help Robin Hood on a very special interactive video mission.

There’ll be FREE LIVE MUSIC in our courtyard both days from 1-5 pm. Saturday, the talented Saturday, the talented Nick Kerzner is scheduled to perform. Nick will be playing original music and covers from the ’60s to today in rock, alternative, and popular genres in an acoustic style. Sunday, popular Long Island singer/songwriter Bryan Gallo takes the stage. Whenever Bryan sets up his guitar and harmonica he’s sure to entertain!

To round out the day there will be pumpkin picking in our 9-acre on-the-vine “u-pick” pumpkin patch, hayrides, great foods to enjoy, Harbes Vineyard’s award-winning wines to sip, vendors, and additional children’s activities.

NOTE: Sunflowers, Robin Hood Corn Maze, Apple Picking & Hayride require admission.

Craft Fair Weekend at The Shoppes

The Shoppes at East Winds, Wading River   |   Saturday, September 16th  &  Sunday, September 17th   11a - 5p

It’s Apple Season on the North Fork and while you’re heading out east visit the Shoppes for shopping, enjoy a bite to eat, and the carousel.

This Weekend, you can also enjoy local craft vendors as well as all The Shoppes have to offer.  Bounce house, Carousel and Face Painting for kids.  Shop Small, Shop Local.

Not Your Early Bird Market & Open Mic

Riverhead Moose Lodge   |   Sunday,  September 17th   12p - 5p

Sleep late and enjoy a leisurely Sunday afternoon. This pop-up market takes place on the scenic Peconic Riverfront in Riverhead, New York. You can shop for handcrafted goods, books and food. Grab a beverage from the River’s Edge Bar & Grill.

  • In addition to the market, there will also be an open mic for musicians, vocalists, comedians, poets, and spoken word artists from 2p – 5p (15-30 minute slots are available). The open mic is open to all levels of performers, so whether you’re a seasoned pro or just starting out, this is a great opportunity to share your talents.
  • Admission is free, so come relax, shop, and sip on the scenic Peconic Riverfront.
  • All genres and ages welcome.PA system, soundboard, and microphone provided. No vulgar language. Covers welcome!
  • To reserve a time slot, please visit riverheadmooselodge.com or text 631-494-2978
  • Drop ins Welcome if slots are available! 
Year Round Your Next Amazing Getaway Could Be On The Beautiful East End of Long Island! We're Not Just Your Weekend Destination Anymore. No Matter the Season, There is a Reason to...End Up Here!

East End Tourism Board of Directors 2023:

Bryan DeLuca - President

Paul Monte - Vice President

Steve Bate - Secretary

Michael Ciaramella
Jennifer Fowkes
Jessica Insalaco
Connie Losandro
Kristen Reyes
Lisa Sannino

Support provided by Market NY through I LOVE NY/ New York State’s Division of Tourism as a part of the Regional Economic Development Council awards, through partnerships with East End Tourism Alliance (EETA) and Discover Long Island.

Copyright © 2023 East End Getaway, All rights reserved.


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