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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Exploring Vineyards in Autumn Splendor

Enjoy Oktoberfest on the East End and all that autumn has to offer outdoors!

Visiting vineyards in the fall provides a unique opportunity for visitors and locals alike to appreciate the art of winemaking on a deeper level. As the vineyards' leaves turn to vibrant shades of red and gold, the process of winemaking comes alive in a symphony of colors and flavors. Strolling through picturesque vineyards, learning about the different grape varieties and the unique characteristics of the region, you can witness the culmination of an entire year's effort by the dedicated winemakers. Tours and tastings become a sensory journey, as you savor a diverse range of wines, each telling a story of the land and the hands that crafted it. Pair your winery excursion with an overnight stay in one of the many hotels, inns or bed and breakfasts the North and South Forks offer to compliment your weekend getaway.

Whether you're a seasoned wine connoisseur or a casual enthusiast, visiting one of the East End's vineyards is an immersive experience offering a deeper connection to the places and people behind the bottle, making it both enriching and unforgettable. For information on East End vineyards and where to stay 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.

*check with each vineyard prior to visiting for seasonal  hours
*photo courtesy of @longislandwinecountry, Mattebella Vineyards, Peconic


Wine by the Vines

Pellegrini Vineyards, Cutchogue   |   Thursday, October 19th   12p - 3p

Be a part of winemaking history and join Southold Historical Museum for “Wine by the Vines” at Pellegrini Vineyards. This popular event is back and promises an afternoon filled with fine wine, delectable food, and great company amidst the beautiful vines on the North Fork. For just $60, you will get to taste several Pellegrini wines, gourmet sandwiches, and sweets. In addition to this, there will be a special wine-themed Bingo included in the event. Celebrate fifty years of Long Island winemaking with Southold Historical Museum and Pellegrini Vineyards in Cutchogue!

Please RSVP in advance at SoutholdHistorical.org, under “Events.”

Haunted Tree House at the Long Island Aquarium


Fridays and Saturdays in October   7p - 9p

Celebrate the season family-style with our Haunted Tree House and its FIVE levels of kid-friendly Halloween fun! This activity is perfect for kids aged 3-11.

•Unlimited time on the Haunted Tree House
•Animal Interactio
•Candy Bags
•Pumpkin Decorating
•Halloween Sand Art
•Halloween Color-A-Button
•$2 Arcade Card

Hot cocoa and festive treats available for purchase at Scoops Ice Cream Shop!
$25pp (+ tax) – One parent free with a paid child.
Aquarium Members: $20pp (+ tax) – Members must purchase in person to get the discounted price.

Walk-ins Welcome!

Entrance to this activity will be at the back of the Aquarium, behind the Hyatt Place Hotel. You’ll enter at the Scoops Ice Cream Shop within the Treasure Cove Resort Marina. There is parking at the marina.

Please note, this is an outdoor activity which will be canceled in the event of significant rain. Check our website and social pages to check for any weather-related cancellations.
Children MUST be accompanied by an adult.

East End Seaport Museum’s 2023 Annual Maritime Festival in Greenport

Fall Festival

The Shoppes at East Wind, Wading River   |   Saturday, October 21st  &  Sunday, October 22nd   11a – 5p

Celebrate Fall at the The Shoppes at East Wind! Families can revel in a delightful mix of seasonal festivities, from face painting to visiting Beyond Crafting Boutique for Daily workshops to create your own Halloween Decorations. Enjoy shopping The Shoppes, local craft vendors and Live Music. Kids will love the grand carousel, the charming wooden train, and the bounce house. Don’t miss the iconic Shoppes Big Chair, and for you favorite Scarecrow Contest. A weekend destination that offers fun for all ages and a perfect way to welcome the fall season! Free Admission.

• Face Painting
• Craft Vendors
• Live Music – Featuring
◦ Grace & Paulie Saturday 1 – 4pm
◦ Sahara Band on Sunday 12 – 3pm Sponsored by Renewal by Anderson
• Bounce house
• Beer Garden at Ruggero’s


Enchanted Forest Trail

Quogue Wildlife Refuge   |   Saturday, October 21st  &  Sunday, October 22nd   12p - 2p

Follow your guide on the Enchanted Forest Trail to meet whimsical, fun, and educational characters. Wear your Halloween costume while learning about animals and nature! Activities, concessions, crafts, and games will be available in the main activity area for before and after your walk.

For children ages 2 to 7 with an adult. Reservations required; please call 631-653-4771 to reserve an arrival time between 12pm – 2pm on the date of your choice. Payment must be provided on the day of at check-in (cash preferred, card accepted as well).

$10 per person

This is a stroller friendly walk (takes approximately 40 – 45 minutes once on the trail).

Pick a day and join us in the Enchanted Forest!

Bridge Gardens Autumn Open House

Peconic Land Trust, Bridgehampton   |   Saturday, October 21st   12p - 3p

Explore Bridge Gardens with our garden wide scavenger hunt, enjoy light refreshments, and channel your inner creativity with a variety of craft activities for children and adults, including pumpkin painting, and create a seasonal front door decoration with Summerhill Landscapes!

Free! Donations appreciated, reservations requested. Rain or shine.

Halloween Fest in Downtown Riverhead

Saturday, October 21st

DTR is annually turned into a Halloween hometown during the month of October when streets are lined with goblins, ghouls, tricks and treats.
Dress the whole family in costume and join us downtown for the festivities!



Bug Light Cruise & Tour

East End Seaport Museum, Greenport   |   Saturday, October 21st   5p - 7p

Tour the inside of Bug Light, the only area lighthouse that allows visitor tours with plenty of time to explore.

Arrive at Museum 30 minutes early. Boat departs Museum at 5:00 PM. Coolers permitted.

Ghost Hunting at Rogers Mansion

Southampton History Museum   |   Saturday, October 21st   7:30p - 10p

Ever wanted to be a ghost hunter? Join the crew of the Long Island Paranormal Investigators as we spend the night exploring the 1843 Rogers Mansion and find out what it really takes to be a Paranormal Investigator. You will get a chance to participate in experiments to test various paranormal theories, learn about the paranormal, hear great spooky stories and maybe even leave with one of your own.

Tours will begin with an introduction to who the Long Island Paranormal Investigators are and a crash course in the theories and devices to interact with and document paranormal beings. Following this 15 minute introduction guests will then begin a 45 minute investigation of the Rogers Mansion to put some of their newly learned theories to the test.


Pumpkin Trail in Sag Harbor

Tuesday, October 31st   3p - 5p

The Sag Harbor Chamber of Commerce has held its annual Halloween Pumpkin Trail for more than 40 years. The first village to offer an opportunity for children to “trick-or-treat” at local businesses, Sag Harbor’s Pumpkin Trail idea soon spread to other villages and areas on the East End. The Pumpkin Trail has become a Sag Harbor tradition everyone looks forward to, with youngsters invited every Halloween to make Sag Harbor’s business district a stop on their trick-or-treat trail.

All children dressed in Halloween costumes can look for Chamber member businesses with a Sag Harbor Chamber Pumpkin Trail sign in their window — an invitation to stop by for some treats — no tricks required!

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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