Where to Eat, Drink and Celebrate Labor Day Weekend in the Hamptons and North Fork

From live music and Montauk waterfront parties to East Hampton brunch and North Fork wine country, here’s where to eat, drink and toast Labor Day weekend.

Labor Day weekend calls for one more sunset drink, one more lobster roll and, apparently, at least one all-white outfit.

Restaurants, resorts and wineries across the Hamptons and North Fork are giving summer a proper send-off with waterfront live music, DJs, brunches, seafood boils, wine and oysters, paella and sangria, and a few parties built for lingering well past dinner.

From Montauk and East Hampton to Southampton and North Fork wine country, here’s where to eat, drink and squeeze a little more summer out of Labor Day weekend.

HAMPTONS

EAST HAMPTON

Labor Day White Party at Sí Sí
Sunday, Sept. 6, 1-5:30 p.m.
Sí Sí, EHP Resort & Marina, East Hampton

Si Si East Hampton Point Resort & Marina

Wear white and head to the water. Sí Sí closes out its regular summer season with its annual Labor Day White Party overlooking Three Mile Harbor. Lohrasp Kansara kicks things off from 1-3:30 p.m., followed by Kasango from 3:30-5:30 p.m. Add Mediterranean-inspired food, cocktails and marina views for one final Sunday afternoon by the water.

Brunch at The Baker House 1650
Friday-Sunday, Sept. 4-6, 11:30 a.m.-1:30 p.m.
The Baker House 1650, East Hampton
$55 per person; advance reservations required

Here’s a new reason to brunch in East Hampton. For the first time, The Baker House 1650 has opened its signature weekend brunch to a limited number of outside guests at the historic Main Street inn.

The Baker House 1650, East Hampton

Only 10 non-hotel guests are accepted for each brunch, making this one to reserve rather than leave to a last-minute Labor Day decision.

WATER MILL

Foie Gras Friday at Bistro Été
Friday, Sept. 4
Bistro Été, Water Mill

Bistro Ete, Water Mill

Start Labor Day weekend on a decidedly French note. Bistro Été’s regular Foie Gras Friday falls on Sept. 4, with a complimentary wine pairing offered with each foie gras order.

It’s not exclusive to Labor Day weekend, but for foie gras fans, the timing works rather nicely.

SOUTHAMPTON

Labor Day Weekend at Southampton Inn
Friday, Sept. 4-Saturday, Sept. 5
Southampton Inn, Southampton

Brianna Tang. Photo courtesy of SH Inn

Start the holiday weekend on a classical note. Pianist Brianna Tang returns to Claude’s on Friday to accompany dinner with works by Cécile Chaminade and Robert Schumann. On Saturday, the action moves poolside for Happy House from 4-6 p.m., with specialty cocktails and complimentary hot dogs. Both inn guests and the public are welcome.

HAMPTONS BAYS

Sunday Paella & Sangria for Two at R.AIRE
Sunday, Sept. 6, 4-9:30 p.m.
R.AIRE at The Hampton Maid, Hampton Bays
$75 for two; Land & Sea upgrade, additional $20

Paella and a pitcher of sangria sound like a pretty good way to spend the last Sunday of summer.

R.AIRE’s Sunday special pairs a choice of paella with a pitcher of red, white or nonalcoholic sangria for two. Choose the Meat Paella with chorizo, Ibérico pork and chicken; Seafood Paella with calamari, mussels, shrimp and clams; or a meat-free Mushroom Fideuà with seasonal mushrooms and aioli.

For an additional $20, the Land & Sea version ups the ante with an 8-ounce Wagyu filet mignon, whole grilled lobster and calamari.

SAG HARBOR

Lunedì Lucci Mondays at Faraway Sag Harbor
Monday, Sept. 7, all day
Faraway Sag Harbor, Sag Harbor

Faraway Sag Harbor

Raise a glass to Labor Day — Italian style. Faraway Sag Harbor is teaming up with Lucci, the sparkling red Lambrusco co-founded by Ashley Graham, to launch Lunedì Lucci Mondays at the hotel’s Lobby Bar & Patio. The special menu pairs Lambrusco by the glass with four sparkling cocktails — the Dirty Lucci Spritz, Negroni Sbagliato Rossa, Lucci French 75 and Lucci Amaro Highball — alongside bites including lamb chips, tuna tartare and a smash burger with fries. The Labor Day kickoff starts a limited series running every Monday in September.

MONTAUK

Labor Day Weekend at The Surf Lodge
Friday and Saturday, Sept. 4-5
The Surf Lodge, Montauk

Surf Lodge, Montauk

The Surf Lodge isn’t letting summer disappear without a soundtrack. The Montauk waterfront hot spot heads into Labor Day weekend with WhoMadeWho on Friday, followed by Carlita and Mochakk on Saturday. Make a night of it with dinner and drinks overlooking Fort Pond before the music takes over.

Live Music at Gosman’s Dock
Thursday-Sunday, Sept. 3-6, 6-9 p.m.
Gosman’s Dock, Montauk

Dinner comes with a soundtrack at Gosman’s Dock over Labor Day weekend. The Montauk Harbor landmark has live music Thursday through Sunday, making it an easy stop for seafood, sunset harbor views and a little music after dinner.

Live music at Gosman’s Dock. Photo: Minskoff Studios

The weekend lineup includes Telly/Hopefully Forgiven on Thursday, Iriespect on Friday, Jettykoon on Saturday and Greyson Little on Sunday.

Website: gosmans.com

Labor Day Weekend at Navy Beach
Saturday-Monday, Sept. 5-7
Navy Beach, Montauk

One more weekend with your feet practically in the sand. Navy Beach heads into Labor Day with waterfront dining, music and drinks on Fort Pond Bay.

DJ Mascari spins Saturday from 5-8 p.m., while Sunday offers another chance for brunch by the water. On Labor Day Monday, the seasonal Après Mondays series goes out with one last round of all-day beverage specials, including $14 rosé, $15 spritzes, $17 Nitro-Tinis and $6 Navy Summer Ale.

Labor Day Weekend at Solé East Resort
Friday, Sept. 4-Sunday, Sept. 6
Solé East Resort, Montauk

Sole East, Montauk, outdoor area.

Solé East keeps the music going all Labor Day weekend with live bands, DJs and a Sunday brunch. Friday starts with live music from Jettykoon from 7-10 p.m., followed by a DJ until 1 a.m. Saturday brings poolside guest DJs from 1-5 p.m. and DJ Matt McCue from 8 p.m.-1 a.m. On Sunday, wind down the weekend with brunch and live music from Julian Link Morse from 11 a.m.-2 p.m.

Labor Day Weekend at Montauk Yacht Club
Friday-Monday, Sept. 4-7
Montauk Yacht Club, Montauk

Alba Spiaggia,. Courtesy of The Montauk Yacht Club

Stretch the holiday weekend out by the marina. Montauk Yacht Club is marking Labor Day with waterfront happenings, dining and live music throughout the weekend, with Alba Spiaggia serving coastal Italian fare overlooking Lake Montauk.

Check the resort’s weekend schedule for individual programming and times.

NORTH FORK

CUTCHOGUE

Labor Day Weekend Garden Party at Meadowlark North Fork
Friday, Sept. 4, 4-8 p.m.
Meadowlark North Fork, Cutchogue

Meadowlark Garden Party, Macari Vineyards, Cutchogue

Start the long weekend among the vines. Meadowlark’s Labor Day weekend Garden Party brings together small-batch wines, canned cocktails and local beer with food from Braun Seafood and The Treatery.

DJ Henry Eau spins from 4:30-7:30 p.m. The party goes on rain or shine, and guests can bring their own chairs and blankets.

Live Music, Oysters & Gelato at Bedell Cellars
Sunday, Sept. 6, 1-5 p.m.
Bedell Cellars, Cutchogue

Wine, oysters, music and gelato — that’s a pretty solid North Fork Sunday.

Rob Europe at Bedell Cellars

Bedell Cellars welcomes guitarist Rob Europe for live music, with fresh oysters from Founders Oyster Farm and a Dorée Gelato pop-up rounding out the afternoon. Grab a glass, find a spot overlooking the vineyard and make an afternoon of it.

JAMESPORT

Wine, Wood-Fired Pizza & Live Music at Jamesport Vineyards
Friday, Sept. 4, 6-8 p.m.
Jamesport Vineyards, Jamesport

Jamesport Vineyards

Pizza, wine and live music get Labor Day weekend started at Jamesport Vineyards. Julian Love performs Friday evening while the winery serves its estate-grown wines alongside wood-fired pizza from its Little Oak kitchen.

SOUTHOLD

Labor Day Weekend at Sparkling Pointe
Friday-Monday, Sept. 4-7
Sparkling Pointe, Southold

There are worse ways to say goodbye to summer than with bubbles and lobster.

Sparkling Pointe Vineyard, Southold

Friday through Sunday, Sparkling Pointe offers a three-wine sparkling flight paired with a lobster roll, North Fork potato chips and dessert. On Labor Day Monday, its Fizz & Fry series pairs méthode Champenoise sparkling wines with a menu of fried favorites, including popcorn chicken, fried shrimp, seafood stuffies, corn fritters and fries.

PECONIC

Live Music at Pindar Vineyards
Saturday and Sunday, Sept. 5-6, 1:30-5:30 p.m.
Pindar Vineyards, Peconic

Pindar Vineyards, Peconic

Keep the North Fork wine-country weekend going with an afternoon at Pindar. The vineyard has live music on its pavilion Saturday and Sunday, with wine available by the glass and bottle and plenty of room to settle in for the afternoon.

ORIENT

Seafood Boil at Duryea’s Orient Point
Labor Day, Monday, Sept. 7, noon-9 p.m.
Duryea’s Orient Point, Orient
$40 per person; minimum three people

Duryeas, Orient

Finish Labor Day weekend with a table full of seafood. Duryea’s Orient Point serves up lobster, snow crab claws and clusters, head-on shrimp, clams and mussels with corn and peewee potatoes in lobster-garlic broth, accompanied by aioli and lemon.

The boil is designed for sharing, with a three-person minimum — and the Orient Point waterfront isn’t a bad place to stretch summer out for a few more hours.

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 .