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.

Southampton “It’s a Wonderful Village”

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

East Hampton Village Holiday Celebration

The East Hampton Holiday Celebration begins with Santa touching down in Herrick Park via Helicopter at 10 a.m., 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 11 a.m. 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 1 p.m. Mrs. Claus will be greeting visitors at the Ladies Village Improvement Society from 2 – 4 p.m.

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 from 9 a.m. to 5 p.m. East Hampton Kitchen will offer homemade holiday cookie tins and seasonal soups available for purchase. Gingerbread house replicas of Mulford Farm, Village Hall and candy land will be on display and raffled off at the Holiday Market at 4:30 p.m. by Mayor Larsen. Raffle tickets will be available for purchase at The Palm, White’s Pharmacy and The Monogram shop where the gingerbread houses will be on display. Proceeds from the Holiday Market will be donated to the East Hampton Food Pantry. The Holiday Market is funded by the East Hampton Village Foundation.

The lawn of The Hunting Inn on Main Street will be transformed into an ice skating rink offering complimentary ice skating, including skates, from 12 p.m. to 6 p.m., made possible by Landry’s. The East Hampton middle school choral group, the Bonnettes, will perform a concert of holiday favorites at 3:45 p.m. 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.m.

Holiday Tree Lighting Ceremony in Orient

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.

Greenport’s Annual Parade of Lights and Tree Lighting

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

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 Southold Local

Holiday Market in Riverhead

East End Food Market’s holiday season opens on Saturday, November 11 from 9:00am – 2:00pm and will run every Saturday through the end of the year.

Stock up on holiday gifts and essentials from over 40 local food, farm and craft vendors. Discover festive flavors, artisanal treats and unique gifts all while supporting your local community.

2nd Annual Magic of Montauk Holiday Fair

The Montauk Chamber of Commerce and Visit Montauk is thrilled to announce the return of our Magic of Montauk Holiday Fair! This second annual event consists of a lit holiday path around the town green, featuring holiday gift vendors, hot cocoa contest, children’s activities, festive treats, food trucks, beer and wine, live music, Santa meet and greet, and LIVE reindeer! Bundle up, grab your loved ones, and don’t miss out on all of the magic Montauk has to offer!

4pm – 7pm – Live Band TBD

*Please note that hot cocoa contest and children’s activities supplies are while supplies lasts.

*Rain date will be 12.10.23