East End Getaway

East End Getaway Long Island's East End is New York's premiere vacation destination for all! A paradise for beach love

Here’s a north fork vineyard you’ll want to add to your East End summer plan 🍇 Peconic Bay Vineyards at 31320 Main Rd. I...
05/29/2026

Here’s a north fork vineyard you’ll want to add to your East End summer plan 🍇

Peconic Bay Vineyards at 31320 Main Rd. In Cutchogue is a family-owned, sustainably farmed winery with hundreds of acres on the north fork of Long Island. Surrounded by vines, it’s one of the largest and most beautiful wine tasting properties on Long Island’s wine trail.

This award winning vineyard features an exceptional wine program that ranges across Rieslings, Chardonnay, Sauvignon Blanc, Merlot, and so many more. The Riesling in particular has become one of the most talked-about wines coming out of this area.

You’ll want to come and stay awhile to enjoy the gorgeous property complete with comfortable outdoor seating areas perfect for couples or your whole friend group. Fire pits, live music and fun events throughout the season all make this the perfect spot for a fun day with friends.

Save this for your North Fork wine country trip & tag who you’re going with. Drop a 🍷 if it’s already on your list!

This past holiday weekend saw the opening of countless businesses across the East End, including the gorgeous Chequit Ho...
05/26/2026

This past holiday weekend saw the opening of countless businesses across the East End, including the gorgeous Chequit Hotel on Shelter Island & we got a sneak peek for you!

Situated between the north & south fork of Long Island, you can access it only by ferry or boat. Just a few minutes from either shore and you’re there.

The Chequit has been welcoming guests to their property since 1872. Sitting high up on a hill, the hotel has beautiful sweeping porches overlooking the harbor, complete with the perfect swing chairs to sit and read your favorite book. The seating areas are airy and full of sunlight and pretty plantings. Each guest room features Italian linens you’ll love to sink in to at the end of your day. Plus a phenomenal restaurant and bar on premises that puts an emphasis on serving local seafood & produce with an Italian flare.

Within walking distance you can find everything from beautiful beaches and trails, to shops, live music, and the most epic sunsets around.

Save this post for your East End trip planning and let us know in the comments if you’ve ever been to Shelter Island! 🛥️ ☀️

Memorial Day Weekend is here and even if the forecast is not cooperating, the East End absolutely is. Both forks are ful...
05/21/2026

Memorial Day Weekend is here and even if the forecast is not cooperating, the East End absolutely is. Both forks are fully open and worth every minute, rain or shine. Here is where we are pointing you this weekend. 🌿

The Long Island Aquarium on East Main Street in Riverhead is one of the best rainy day destinations on the East End. Sharks, penguins, touch tanks, and if you’re feeling adventurous, ask about the shark dives!

The Westhampton Beach Fine Art Festival is on the Great Lawn on Main Street in Westhampton Beach this Saturday May 23 from 10 AM to 6 PM and Sunday May 24 from 11 AM to 6 PM. Free admission, artists from across the country, and original works in sculpture, jewelry, painting, photography, glass, and more. Check their website for weather updates.

Up on the North Fork, Peconic Bay Vineyards in Cutchogue is open Friday through Sunday noon to 6 PM with a beautiful indoor tasting experience, an oyster and wine bar, and outdoor fire pits overlooking the vines if the weather cooperates.

North Fork Brewing Company at 24 East 2nd Street in Riverhead has been pouring craft beer in a converted firehouse since 2018. Bring a board game and the dog for a perfect rainy afternoon.

And at The Suffolk Theater in Riverhead, the Lords of 52nd Street featuring Liberty DeVitto and Russell Javors perform Billy Joel’s greatest hits as they were originally recorded. One of the best live music nights of the entire weekend.

Beyond these highlights the bars, restaurants, boutiques, and galleries across both forks are all open and ready for the season. The East End does not need sunshine to deliver, it just needs you to show up. 🗺️

Save this and share it with whoever you are coming out with. 👇

We kicked off the season by finding the perfect new summer spot on the North Fork! 🍋 Saylor Beach House is the newest ad...
05/19/2026

We kicked off the season by finding the perfect new summer spot on the North Fork! 🍋

Saylor Beach House is the newest addition to the iconic Claudio’s Marina property located in Greenport, NY. This Mediterranean- inspired restaurant & bar is the place to go when you want to lounge, soak up some sun, and catch the breeze with a gorgeous drink in hand. The relaxed vibe, set dockside and under gently flapping awnings, made us feel like we were sipping cocktails on the French Riviera.

Launching this Memorial Day Weekend, this is a spot you’ll want to check out for yourself! The laidback atmosphere is perfect for when you need an escape from reality that happens to include a delicious Mediterranean- inspired menu, all the water views, and a sun-drenched aesthetic that will leave your friends feeling jealous when they see your weekend pics.

They’re even taking it to a whole new level by debuting a new partnership with Yacht Hampton that will provide white glove service as you cruise from Sag Harbor to Greenport aboard one of their premium vessels for a true dock to dine experience. The service will run Thursday through Sunday all season long, and you’ll want to check this out. Their captain and staff were incredible as we made our way across the harbor, and it made the day feel even more special.

If you’re starting to make your summer plans to the East End, your trip won’t be complete without a stop here!

Tag a friend you want to bring along, and let us know in the comments if you’re adding this stop to your East End bucket list! 👇🍋🍹

After a morning on the America 250th trail in Southampton, or a day spent shopping on Main, this is exactly where you wa...
05/14/2026

After a morning on the America 250th trail in Southampton, or a day spent shopping on Main, this is exactly where you want to end up.🍺

The Southampton Publick House on Jobs Lane is steps from every history stop we have featured in this series and one of the most consistently beloved restaurants in Southampton Village, open year-round for locals and visitors alike.

Great burgers, local seafood, Long Island crab cakes, and a solid craft beer program with five permanent brews on tap. Plus a friendly staff that makes you want to stay awhile.

Happy hour Monday through Friday 4 to 7 PM. Weekend brunch Saturday and Sunday.

This place has been a staple for decades and has plenty of history on its own. Make sure to save this post and add it to your list 🗺️

📍 62 Jobs Lane, Southampton
Open daily from 11:30 AM
Tag who you are going with. 👇

If you have been following our East End America 250th trail from the beginning, this stop connects directly back to wher...
05/14/2026

If you have been following our East End America 250th trail from the beginning, this stop connects directly back to where it all started.

Thomas Halsey and his family were among Southampton’s earliest English colonists, sailing from England in the 1630s seeking religious freedom. By 1648 Thomas Sr. had acquired land on South Main Street and the current saltbox-style house was built beginning around 1683 by his son Thomas Jr.

The house is believed to be the oldest English-style house in New York State. It’s filled with 17th and 18th century furnishings donated by local families, a kitchen with an original wide open-hearth fireplace, and in the backyard a Colonial revival-style garden that replicates an 18th century herb garden, perennial border, and apple orchard.

The Halsey family connection to Southampton goes all the way back to the 1640 landing at Conscience Point, the very first stop in this series. Thomas Halsey Sr. was one of the original settlers who came ashore that June morning in 1640. The homestead his family built is the physical continuation of that founding story, just half a mile south on Main Street.

The house opens for free self-guided tours on Saturdays from June 6th through August 29th, 11 AM to 4 PM. The grounds and gardens are open year-round from sunrise to sunset and worth visiting now while the herb garden and apple orchard are coming into their spring bloom.

This serene historic site is the perfect addition to your Southampton 250th itinerary. Save this post and make sure to go back and check out the other stops we’ve featured!

📍 249 South Main Street, Southampton
Grounds open year-round, dawn to dusk
Interior tours Saturdays June 6 through August 29, 11 AM to 4 PM. Free admission.

Save this and tag someone who needs to see this place. Drop a ⭐ if it’s going on your list!

Mother’s Day is this Sunday and if you’re still looking for something beyond the usual brunch reservation or dinner out,...
05/06/2026

Mother’s Day is this Sunday and if you’re still looking for something beyond the usual brunch reservation or dinner out, the East End has you covered on both forks. 🌸

A beach picnic on the South Fork. A piece of handcrafted jewelry from one of the oldest silversmith shops in America. Wine tasting on 90 acres of North Fork vineyard. A walk through 16 acres of sculpture gardens in East Hampton. Being surrounded by beautiful tulips while you relax with a beer in hand.

However you like to celebrate the moms in your life, there is something out here that will make her feel special and like you put a lot of thought into her day.

Swipe through for ideas on both forks and tag your mom or share this with someone who still needs a plan. 🌸

The East End has a lot going on this weekend and one of the most exciting things happening is the 76th season opener at ...
04/30/2026

The East End has a lot going on this weekend and one of the most exciting things happening is the 76th season opener at Riverhead Raceway, Long Island’s only NASCAR stock car track. 🏁

Saturday May 2nd is NASCAR Pack the Track Night with opening ceremonies at 6:30 PM and gates opening at 5:00 PM. Seven NASCAR feature events are on the card led by the Buzz Chew Chevrolet NASCAR Modified 50-lapper, joined by the Late Models, Eagle Chevrolet Crate Modifieds, TK Figure Eights, Blunderbusts, Super Pro Trucks, and INEX Legend Race Cars.

And the weekend keeps going Sunday May 3rd with the May Meltdown program featuring Street Stocks, Mini Stocks, INEX Bandoleros, Truck Enduro, and a Women’s 4/6-Cylinder race, with gates opening at noon and racing starting at 1:30 PM.

This is one of those East End experiences that always surprises people the first time they go. The quarter-mile high-banked oval is loud, fast, and incredibly fun whether you are a lifelong racing fan or someone who has never watched a stock car race in their life. It is the kind of Saturday night that reminds you why people love this part of Long Island so much.

📍 Riverhead Raceway 1797 Old Country Road, Riverhead, NY riverheadraceway.com

Tag someone you’re taking to opening night. Drop a 🏁 if you have a favorite team!

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431 E Main Street
Riverhead, NY
11901

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