Holidays on the East End
Spending the holidays on the East End of Long Island is a festive immersion into the heartwarming traditions and community spirit that define the season.
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The Magic of Holiday Traditions on the East End 
Spending the holidays on the East End of Long Island is a festive immersion into the heartwarming traditions and community spirit that define the season. Santa visits add a sprinkle of magic as children eagerly share their wishes with the jolly old man in red. The streets come alive with enchantment during parades, where vibrant light displays and joyful tunes captivate audiences of all ages. Holiday markets offer a treasure trove of unique gifts and local delights, creating a merry atmosphere for shoppers. The illumination of towering trees during tree lightings turns villages into winter wonderlands, fostering a sense of togetherness and joy. Amidst the picturesque landscapes, the East End becomes a haven for families and friends to embrace the holiday cheer, forging memories that echo the warmth of community and the festive spirit that defines this special time of year.

Explore our town-by-town guide to the holiday festivities happening across the North and South Forks this weekend. With strategic planning, you might even catch a glimpse of Santa more than once!

For additional information on where to dine and stay during your weekend and holidays, visit, your destination guide for all things on the East End Al Fresco!

*photo courtesy of Diane Tucci 

Lighting the Big Duck in Flanders

1012 NY-24, Flanders, NY   |   Wednesday, November 29th   7p - 9p

Apart of the National Register of Historic Places, the Big Duck is a sight to see and the annual lighting is a community event to not be missed! The event features a visit from Quackerjack, the Long Island Ducks baseball team mascot, carols led by students from the Riverhead Middle School Show Choir, refreshments and the ever-anticipated arrival of Santa Claus by fire truck.

*photo courtesy of Riverhead Local



27320 Route 25 Cutchogue, NY 11935   |   Saturday, December 2nd   11a - 3:30p

This one-day event was created to promote Cutchogue & North Fork businesses during the long winter months of the off-season. Six stops on the tour will showcase two Inns festively decorated for the holidays, Sannino Vineyard B&B and Blue Iris B&B.

Each of the stops will feature a special treat such as wine from a local vineyard, cookies, hot cider, cheese, and a little bite from a local restaurant. Sannino Vineyard Tasting House, Alex Ferrone Art Gallery and The French Picnic are also stops along the way. The day will include a tour of the Cutchogue New Suffolk Historical Council’s Old House and wrap up with their Annual Tree Lighting. We will be collecting unwrapped toys for Toys for Tots.

Annual Christmas Tree Lighting on the
Cutchogue Village Green

Saturday, December 2nd   3:30p

Starting at 3:30 with hot cider and treats. 4:00 gather for carols before the tree lighting and 4:30 visit from Santa. (times approximate) Visit the Pop-up Christmas shop at the Carriage house! Rain Date Dec. 3rd.

2023 Greenport Shellabration

Greenport Village   |   Saturday, December 2nd  &  Sunday, December 3rd   
12p - 4p

Shellabration is back!
Participants gain access to Greenport’s finest establishments to enjoy local shellfish, wine and beer pairings during a weekend long restaurant walk. All proceeds generated from wristband sales will support Cornell Cooperative Extension Marine Program’s shellfish restoration and community stewardship projects-specifically the SPAT Program (Suffolk Project in Aquaculture Training) and Back to the Bays Initiative.

Participating restaurants will offer those wearing official Shellabration wristbands access to small plate menu items featuring local shellfish, paired with tasting pours of Long Island wine, craft beer and spirits. Additionally, local shops will be offering special promotions for Shellabration participants, making for a wonderful weekend of eating, drinking and shopping local, all in support of our marine environment!

It is highly recommended that Shellabrants reserve wristbands in advance, as this event sells out every year. Upon checking in, you will be treated to a complimentary first pairing of clams and oysters on the half shell and a local craft beverage tasting.


Greenport’s Annual Parade of Lights and Tree Lighting

Saturday, December 2nd   5p - 7p

See wow around every corner at the Village of Greenport’s annual Parade of Lights and tree lighting. The parade will kick off at 5 p.m. from the corner of Main and Center Streets and will continue through the village to Mitchell Park where the Christmas tree will be lit for the season.

Rain Date Dec. 3.

Santa Day in Mattituck

Veteran's Memorial Park Recreation Center
Saturday, December 2nd   12p - 2p

After many years of Santa Day at the Mattituck Shopping Center, we have teamed up with the Mattituck Parks Department and moved Santa Day to it’s new location to Mattituck Veteran’s Memorial Park’s Recreation Center!

The fun starts at Noon with Hot Dogs, Ice Cream, Candy, and Hot Chocolate. There will be indoor games and lots of space for the kids to run around outside while waiting for Santa!

Santa and Mrs. Claus will arrive at 1:00pm on a Mattituck Fire Department Fire Truck, and then head inside for pictures! 

Veteran’s Memorial Park is located off Peconic Bay Blvd and Bay Ave.

All are welcome and we’ll see you there!

*photo courtesy of SoutholdLocal

Holiday Tree Lighting Ceremony in Orient

Orient Beach State Park   |   Saturday, December 2nd   5:30p

Join us in lighting the tree at our annual Holiday Tree Lighting Ceremony at Orient Beach State Park. The tree is lit by Santa and then he will be available for pictures afterwards. Hot chocolate and cookies will be served. In the spirit of the season the Park will be collecting winter coats and non-perishable food items for families in need.

Southold Historical Museum Holiday Fair

Southold Town Recreation Center, 970 Peconic Lane, Peconic, NY 
Saturday, December 2nd   9a - 4p

This a wonderful opportunity to celebrate the season and to find some unique gift items from a variety of vendors and talented local artisans.

A “Holiday Auction” will feature gift baskets for all ages. Take a chance to win one for yourself or to give as a holiday gift.

There will be a bake sale and ‘café’ for snacks, as well as crafts for children. Families won’t want to miss a visit with Santa who will be on hand to greet children from 11am-1pm.
Admission to the event is free.


Shelter Island Chamber of Commerce Tree Lighting

Town of Shelter Island Police Dept. Headquarters
Tuesday, December 5th   5p

You don’t want to miss this quintessential community holiday event!

Join usfor music and caroling, and the ceremonial lighting of the Town tree.

Then walk on down to the American Legion to warm up with some hot chocolate and homemade cookies, and have your photo taken with Santa Claus.

Free Admission. All welcome!


11TH ANNUAL WOODEN WONDERLAND: Holiday Craft Show & Sale!

Suffolk County Historical Society, Riverhead
Saturday, December 2nd   10a - 4p

Our annual family-friendly event will feature handmade wooden items as well as other local artisans’ wares. Features include holiday art & crafts, ornaments, home décor, rustic Santas and gnomes, unique handmade carvings, handmade candles and soaps, hats, and scarves, wreaths, pottery, clothing, and more! There will be something for everyone on your holiday gift list! Live woodworking and woodcarving demonstrations will go on all day indoors in our historic galleries and outdoors on our Great Lawn. Fun for the whole family! Free admission!

More info.: 631-727-2881 x100.

Long Island Railroad Museum Holiday Open House with Santa

Visitors Center & Restoration Site,  416 Griffing Avenue, Riverhead
Saturday, December 2nd   11:30a - 3p

Santa arrives from the North Pole on our Fairbanks-Morse four man track speeder at 12 Noon each day with a gift for all good boys and girls.  Refreshments will be served and a LIONEL “Winter Wonderland” Toy Trainset will be raffled at Greenport on Sunday, December 10th at 2:00 PM.  For the train lover on your list, our Gift Shops will be open for holiday shopping.
 Admission is FREE and everyone is welcome.

Riverhead Tree Lighting

Saturday, December 2nd   1:30p - 5p

Holiday fun for all ages and your animals! There will be events from the Paws & Claus Pet Parade to the Goat on a Boat Puppet show & crafts!

*photo courtesy of Discover Long Island

7th Annual Holiday Tree Lighting with
Santa at The Shoppes

East Wind, Wading River   |   Saturday, December 2nd   4p - 8p

Stop by to put a letter in Santa’s mailbox* , enjoy our live DJ entertainment with LI Sound Entertainment and dance number by All Star Dance Academy, Ride Rudolph on the Carousel and more holiday fun including holiday shopping.  Santa arrives on a Wading River Fire Department Fire Truck at 6pm to light the tree.  Bring a new unwrapped toy to support Toys for Tots and the US Marines and bring your camera to take free photo with Santa.  
Admission is free.
Rain Date Sunday, December 3.

*Mail your letters before December 19 to get a return letter back from Santa!

For more information please call 631-846-2372

Jamesport Tree Lighting and Holiday Celebration

George Young Community Center   |   Wednesday, December 6th   6:30p

Jamesport will celebrate the holidays with a tree lighting, Christmas caroling and a visit from Santa!  Hosted by the Jamesport Fire Department and the Greater Jamesport Civic Association.
Free hot chocolate served by Duffy’s Deli and the Treatery.

*photo courtesy of Riverhead Local


2nd Annual Holiday on Main in East Quogue

Saturday, December 2nd  |  2p - 6p

Celebrate the Holidays in East Quogue during the Annual Holiday on Main Street (from Lewis Road east to past Bay Avenue/EQFD).  The road will be closed to vehicular traffic during that time. 

There will be vendors, food trucks, and activities, plus a holiday dog costume parade! Letters and Photos with Santa!
Tree lighting hosted by East Quogue Civic at the Village Green at 5p.

All are welcome!


Long Wharf, Sag Harbor   |   Saturday, December 2nd   4:15p - 5:30p

Help us light up Sag Harbor with the spirit of the season! The festivities start at 4:15 on Long Wharf at the Bay Street Theater courtyard with holiday music by Sarah Conway and the Playful Souls. The Dickens Carolers will join in and the tree lighting will take place at approximately 5pm. Music and celebration will end at 5:30 p.m. 

sag harbor long wharf | Map

Southampton “It’s a Wonderful Village”

Saturday, December 2nd 

11:30 am – 3:30 pm Nostalgic Electric Train Ride
15 W Main Street (Behind Hildreth’s Outdoor Store)

1:30 pm -3:30 pm Santa at the Chamber
76 Main Street

2:00 pm- 4:00 pm Holiday Carolers
Strolling throughout the Village

Winter Festival in Westhampton Beach

Westhampton Beach Village   |   Saturday, December 2nd   11a - 6p

11 AM – 5 PM Main Street will be closed to traffic. • Check Chamber of Commerce website often for updates to schedule & festivities

Artisan Vendors
Beachglass and Burlap, Create & Imaginate, Curiously Creative Candles, Geri Besca Jewelry, Lulu Knits, Moon Breeze Mercantile, Nannyecrafts, Pawcasso Art Studio & Pet Boutique, Silk and Sea Designs

Beer Garden
Westhampton Beach Brewing Company

Christmas Trees & Wreaths
Bay Gardens

Family Activities
Inflatable Gingerbread Bouncy House & Slide
Sponsored by the Nydegger Family
Inflatable Snow Globe
“Walking Circus Performers” by Island Cirque

Food Vendors
Arlotta Food Studio, LLC, Founders Oyster Farm, J & A’s Gluten Free, Sal & Jerry’s, BakerySugar Sweet, Sweet Legends Bakeshop, Terra Nut, Tommy Pickles

Food Trucks & Restaurants
Brunetti’s Pizza Wine BarEmily’s Apple PuffsFlora & FaunaGood BickleIsland EmpanadaKnot of This World PretzelsMeats MeatSalt+Loft

Informational Vendors
New York Life – Daniel Piedra

11AM – 1 PM Brooklyn Tim Performs Live
1PM – 4PM DJ Eclipse and Traveling Photo Booth
Sponsored by New York Cancer & Blood Specialists

Santa Con Style Pet Parade
Meet at 4 PM in front of the Westhampton Beach Performing Arts Center. The parade will begin at 4:30 PM and travel east on Main Street to The Village Green where it will end.
Parade in partnership with The Southampton Animal Shelter Foundation

5PM - 6PM Christmas Tree and Menorah Lighting at The Village Green


East Hampton Village Holiday Celebration

Saturday, December 2nd   9a - 5p

An exciting new addition to the Holiday Celebration is the first annual Village Holiday Market. Held on the front lawn of East Hampton Village Hall at the corner of Huntting Lane and Main Street, the market will offer an array of holiday greenery, decorations and treats as well as an assortment of specially crafted gingerbread houses.

At 10a Santa touches down in Herrick Park via Helicopter courtesy of the PBA! Santa’s arrival will be accompanied by the Dressen’s food truck providing free doughnuts and hot cocoa to all of Santa’s fans. The annual Santa Parade will follow at 11a featuring floats from community groups, marching bands and of course, Santa and Mrs. Claus on the holiday sleigh. Following the parade, a complimentary holiday movie will be screened at the Regal theater on Main Street at 1p Mrs. Claus will be greeting visitors at the Ladies Village Improvement Society from 2 – 4p.

The lawn of The Hunting Inn on Main Street will be transformed into an ice skating rink offering complimentary ice skating, including skates, from 12p to 6p, made possible by Landry’s. The East Hampton middle school choral group, the Bonnettes, will perform a concert of holiday favorites at 3:45p on the Village Hall lawn. Additionally, John Pappas, Cittanouva, Tutto Caffe and The Palm will offer lunch and dinner specials in honor of the holiday kick off. The ARF adoption truck will be parked behind Village Hall with dogs, cats, puppies and kittens available for adoption into their forever homes.

Finally to cap off the holiday celebration there will be a tree lighting adjacent from the East Hampton post office on Gay Lane at 5p.

*photo courtesy of


Historic Holidays at Hallockville

Hallockville Museum Farm, Riverhead   |   Sunday, December 3rd   12p - 3:30p

Hallockville Museum Farm, an authentic, preserved 28-acre North Fork farm homestead, invites visitors to experience old-fashioned holiday traditions during the Historic Holidays at Hallockville open house on Sunday, December 3, from 12:00 – 3:30 p.m. Costumed docents will lead tours of historic homes at Hallockville, while sharing stories of past holiday celebrations. The Hallock Homestead, which is listed on the National Register of Historic Places, will be decorated for a Victorian Christmas. In the Cichanowicz Farmhouse, docents will recreate a Polish Christmas Eve celebration from the 1930s. Visitors may view an exhibit of antique toys, take in the aroma of baking in an antique wood stove, and  learn how Christmas celebrations were banned by early East End settlers and eventually came to the North Fork primarily as a secular celebration.

The event is free and open to the public as Hallockville’s holiday gift to the community. Hallockville Museum Farm is located at 6038 Sound Ave. in Riverhead.


Downtown Riverhead’s Annual Holiday Parade + Bonfire

Saturday, December 9th   |   3p - 5p
Rain date December 16th

2nd Annual Magic of Montauk Holiday Fair

Montauk Town Green   |   Saturday, December 9th   2p - 7p
Rain date Sunday, December 10th

The Nutcracker

Westhampton Beach Performing Arts Center
Saturday, December 9th  &  Sunday, December 10th

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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